# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shi_2389_nica
_database_code_depnum_ccdc_archive 'CCDC 1834419'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2018-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H14 N2'
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H40 N2 O3'
_chemical_oxdiff_usercomment     S_45
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y+1/2, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y-1/2, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y, z-1/2'

_cell_length_a                   19.954(3)
_cell_length_b                   9.7592(12)
_cell_length_c                   7.2875(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1419.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    848
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      28.6940
_cell_measurement_theta_min      2.3160
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3565
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.32
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   56.00   83.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.5133   77.0000   67.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   51.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.5133   77.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega    0.00   58.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       16.5133   77.0000  -60.0000 58
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0297474000
_diffrn_orient_matrix_UB_12      0.0010193000
_diffrn_orient_matrix_UB_13      -0.0533289000
_diffrn_orient_matrix_UB_21      0.0027056000
_diffrn_orient_matrix_UB_22      -0.0721151000
_diffrn_orient_matrix_UB_23      0.0086480000
_diffrn_orient_matrix_UB_31      -0.0193162000
_diffrn_orient_matrix_UB_32      -0.0084443000
_diffrn_orient_matrix_UB_33      -0.0809852000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1012
_reflns_number_total             1262
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0449
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0497P)²+0.0673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1091
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N 0.25258(7) 0.09270(14) 0.3669(2) 0.0305(4) Uani 1 d . . 1 . . .
C1 C 0.0000 0.7183(2) 0.2500 0.0309(6) Uani 1 d . . 2 S T P
H1 H 0.0000 0.8136 0.2500 0.037 Uiso 1 calc . . 2 RS T P
C2 C 0.05960(8) 0.65813(16) 0.3053(2) 0.0279(4) Uani 1 d . . 1 . . .
H2 H 0.0931 0.7184 0.3422 0.033 Uiso 1 calc . . 1 R . .
C3 C 0.07609(8) 0.52015(15) 0.3131(2) 0.0236(4) Uani 1 d . . 1 . . .
H3 H 0.1197 0.5008 0.3501 0.028 Uiso 1 calc . . 1 R . .
C4 C 0.03631(8) 0.40656(15) 0.2731(2) 0.0199(4) Uani 1 d . . 1 . . .
C5 C 0.05665(8) 0.26771(16) 0.2829(2) 0.0208(4) Uani 1 d . . 1 . . .
C6 C 0.0000 0.1870(2) 0.2500 0.0230(6) Uani 1 d . . 2 S T P
H6 H 0.0000 0.0917 0.2500 0.028 Uiso 1 calc . . 2 RS T P
C7 C 0.12420(8) 0.21232(16) 0.3166(2) 0.0218(4) Uani 1 d . . 1 . . .
C8 C 0.18229(8) 0.27279(16) 0.2482(2) 0.0240(4) Uani 1 d . . 1 . . .
H8 H 0.1798 0.3548 0.1836 0.029 Uiso 1 calc . . 1 R . .
C9 C 0.24372(8) 0.21055(17) 0.2766(2) 0.0284(4) Uani 1 d . . 1 . . .
H9 H 0.2815 0.2538 0.2296 0.034 Uiso 1 calc . . 1 R . .
C10 C 0.13300(8) 0.08952(15) 0.4120(2) 0.0272(4) Uani 1 d . . 1 . . .
H10 H 0.0962 0.0447 0.4620 0.033 Uiso 1 calc . . 1 R . .
C11 C 0.19627(9) 0.03471(17) 0.4321(2) 0.0305(4) Uani 1 d . . 1 . . .
H11 H 0.2003 -0.0478 0.4949 0.037 Uiso 1 calc . . 1 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 C9 1.337(2) . ?
N1 C11 1.345(2) . ?
C1 C2 1.3863(19) 4 ?
C1 C2 1.3863(19) . ?
C2 C3 1.387(2) . ?
C3 C4 1.394(2) . ?
C4 C4 1.488(3) 4 ?
C4 C5 1.416(2) . ?
C5 C6 1.3984(19) . ?
C5 C7 1.473(2) . ?
C6 C5 1.3984(19) 4 ?
C7 C8 1.393(2) . ?
C7 C10 1.397(2) . ?
C8 C9 1.384(2) . ?
C10 C11 1.379(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
C9 N1 C11 115.17(15) . . ?
C2 C1 C2 129.9(2) . 4 ?
C1 C2 C3 128.79(17) . . ?
C2 C3 C4 128.92(16) . . ?
C3 C4 C4 127.00(9) . 4 ?
C3 C4 C5 125.95(15) . . ?
C5 C4 C4 106.89(9) . 4 ?
C4 C5 C7 128.45(14) . . ?
C6 C5 C4 107.37(14) . . ?
C6 C5 C7 124.17(15) . . ?
C5 C6 C5 111.45(19) 4 . ?
C8 C7 C5 123.12(15) . . ?
C8 C7 C10 115.93(15) . . ?
C10 C7 C5 120.86(14) . . ?
C9 C8 C7 119.83(16) . . ?
N1 C9 C8 124.66(16) . . ?
C11 C10 C7 120.05(15) . . ?
N1 C11 C10 124.35(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C3 H3 N1 0.93 2.70 3.513(2) 145.8 7_665

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_2617_sini
_database_code_depnum_ccdc_archive 'CCDC 1834435'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2018-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H15 N2, C20 H14 N2, C8 H6 O4'
_chemical_formula_sum            'C48 H35 N4 O4'
_chemical_formula_weight         731.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H25 N2 O4'
_chemical_oxdiff_usercomment     S_44
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, z'

_cell_length_a                   12.4512(9)
_cell_length_b                   19.7388(14)
_cell_length_c                   14.6081(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3590.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1556
_cell_measurement_temperature    172.8(3)
_cell_measurement_theta_max      24.8360
_cell_measurement_theta_min      2.1310
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1532
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9600
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.73
_diffrn_ambient_temperature      172.8(3)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -4.00   24.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690  -99.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00   52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690   77.0000  -60.0000 93

#__ type_ start__ end____ width___ exp.time_
  3 omega   37.00   79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690   57.0000 -180.0000 42
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0047042000
_diffrn_orient_matrix_UB_12      -0.0352357000
_diffrn_orient_matrix_UB_13      -0.0084698000
_diffrn_orient_matrix_UB_21      -0.0563517000
_diffrn_orient_matrix_UB_22      -0.0021291000
_diffrn_orient_matrix_UB_23      -0.0066466000
_diffrn_orient_matrix_UB_31      0.0071102000
_diffrn_orient_matrix_UB_32      0.0066195000
_diffrn_orient_matrix_UB_33      -0.0473498000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2306
_reflns_number_total             3269
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0559
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0615P)²+0.8033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1477
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C25(H25), C26(H26), C27(H27), C3(H3),
 C4(H4), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
N1 N -0.01843(17) 0.49242(10) 0.13816(15) 0.0341(6) Uani 1 d . . 1 . . .
C6 C -0.0900(2) 0.54104(12) 0.11795(19) 0.0370(7) Uani 1 d . . 1 . . .
H6 H -0.1627 0.5312 0.1244 0.044 Uiso 1 calc . . 1 R . .
C7 C -0.0613(2) 0.60497(12) 0.08810(18) 0.0328(6) Uani 1 d . . 1 . . .
H7 H -0.1142 0.6366 0.0742 0.039 Uiso 1 calc . . 1 R . .
C8 C 0.04679(19) 0.62219(11) 0.07880(16) 0.0238(6) Uani 1 d . . 1 . . .
C9 C 0.12024(19) 0.57115(11) 0.09972(17) 0.0265(6) Uani 1 d . . 1 . . .
H9 H 0.1935 0.5796 0.0947 0.032 Uiso 1 calc . . 1 R . .
C10 C 0.0852(2) 0.50835(12) 0.12769(17) 0.0315(6) Uani 1 d . . 1 . . .
H10 H 0.1363 0.4752 0.1400 0.038 Uiso 1 calc . . 1 R . .
C11 C 0.07908(19) 0.69134(10) 0.05330(16) 0.0239(6) Uani 1 d . . 1 . . .
C12 C 0.0233(3) 0.7500 0.0798(2) 0.0244(8) Uani 1 d . . 2 S T P
H12A H 0.0141 0.7500 0.1457 0.029 Uiso 1 calc . . 2 RS T P
H12B H -0.0474 0.7500 0.0519 0.029 Uiso 1 calc . . 2 RS T P
C13 C 0.17355(19) 0.71240(11) 0.00668(15) 0.0218(5) Uani 1 d . . 1 . . .
C14 C 0.24862(19) 0.67020(12) -0.03512(16) 0.0267(6) Uani 1 d . . 1 . . .
H14 H 0.2327 0.6242 -0.0331 0.032 Uiso 1 calc . . 1 R . .
C15 C 0.3440(2) 0.68683(12) -0.07949(16) 0.0299(6) Uani 1 d . . 1 . . .
H15 H 0.3850 0.6503 -0.0992 0.036 Uiso 1 calc . . 1 R . .
C16 C 0.3862(3) 0.7500 -0.0983(2) 0.0302(8) Uani 1 d . . 2 S T P
H16 H 0.4525 0.7500 -0.1277 0.036 Uiso 1 calc . . 2 RS T P
N2 N 0.35784(18) 0.51358(11) -0.03145(18) 0.0405(6) Uani 1 d . . 1 . . .
C17 C 0.3591(2) 0.46542(13) 0.0330(2) 0.0393(7) Uani 1 d . . 1 . . .
H17 H 0.3388 0.4775 0.0921 0.047 Uiso 1 calc . . 1 R . .
C18 C 0.3886(2) 0.39880(12) 0.01759(18) 0.0336(6) Uani 1 d . . 1 . . .
H18 H 0.3872 0.3676 0.0653 0.040 Uiso 1 calc . . 1 R . .
C19 C 0.42032(19) 0.37888(11) -0.06911(17) 0.0269(6) Uani 1 d . . 1 . . .
C20 C 0.4170(2) 0.42854(12) -0.13700(19) 0.0330(6) Uani 1 d . . 1 . . .
H20 H 0.4351 0.4177 -0.1970 0.040 Uiso 1 calc . . 1 R . .
C21 C 0.3870(2) 0.49370(13) -0.1149(2) 0.0391(7) Uani 1 d . . 1 . . .
H21 H 0.3871 0.5259 -0.1614 0.047 Uiso 1 calc . . 1 R . .
C22 C 0.45352(19) 0.30853(11) -0.08758(16) 0.0252(6) Uani 1 d . . 1 . . .
C23 C 0.4034(3) 0.2500 -0.0540(2) 0.0265(8) Uani 1 d . . 2 S T P
H23 H 0.3447 0.2500 -0.0146 0.032 Uiso 1 calc . . 2 RS T P
C24 C 0.54161(19) 0.28772(11) -0.14141(16) 0.0260(6) Uani 1 d . . 1 . . .
C25 C 0.6192(2) 0.33016(13) -0.17935(17) 0.0339(6) Uani 1 d . . 1 . . .
H25 H 0.6072 0.3763 -0.1716 0.041 Uiso 1 calc . . 1 R . .
C26 C 0.7118(2) 0.31356(15) -0.22700(18) 0.0405(7) Uani 1 d . . 1 . . .
H26 H 0.7518 0.3500 -0.2486 0.049 Uiso 1 calc . . 1 R . .
C27 C 0.7528(3) 0.2500 -0.2469(3) 0.0428(10) Uani 1 d . . 2 S T P
H27 H 0.8177 0.2500 -0.2783 0.051 Uiso 1 calc . . 2 RS T P
O1 O -0.07521(14) 0.37396(8) 0.20365(13) 0.0384(5) Uani 1 d . . 1 . . .
H1 H -0.0584 0.4115 0.1842 0.058 Uiso 1 calc . . 1 GR . .
O2 O -0.21774(15) 0.43048(8) 0.25564(12) 0.0401(5) Uani 1 d . . 1 . . .
C1 C -0.1682(2) 0.37778(12) 0.24455(17) 0.0283(6) Uani 1 d . . 1 . . .
C2 C -0.2120(2) 0.31102(11) 0.27681(16) 0.0261(6) Uani 1 d . . 1 . . .
C3 C -0.3053(2) 0.31050(12) 0.32851(17) 0.0316(6) Uani 1 d . . 1 . . .
H3 H -0.3370 0.3513 0.3455 0.038 Uiso 1 calc . . 1 R . .
C4 C -0.3516(3) 0.2500 0.3550(2) 0.0345(9) Uani 1 d . . 2 S T P
H4 H -0.4137 0.2500 0.3904 0.041 Uiso 1 calc . . 2 RS T P
C5 C -0.1642(3) 0.2500 0.2521(2) 0.0253(8) Uani 1 d . . 2 S T P
H5 H -0.1004 0.2500 0.2191 0.030 Uiso 1 calc . . 2 RS T P


_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 1.343(3) . ?
N1 C10 1.337(3) . ?
C6 C7 1.382(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.394(3) . ?
C8 C11 1.471(3) . ?
C9 C10 1.376(3) . ?
C11 C12 1.404(3) . ?
C11 C13 1.421(3) . ?
C12 C11 1.404(3) 8_575 ?
C13 C13 1.484(4) 8_575 ?
C13 C14 1.393(3) . ?
C14 C15 1.392(3) . ?
C15 C16 1.381(3) . ?
C16 C15 1.381(3) 8_575 ?
N2 C17 1.338(3) . ?
N2 C21 1.332(4) . ?
C17 C18 1.384(3) . ?
C18 C19 1.384(3) . ?
C19 C20 1.395(3) . ?
C19 C22 1.474(3) . ?
C20 C21 1.378(3) . ?
C22 C23 1.402(3) . ?
C22 C24 1.411(3) . ?
C23 C22 1.402(3) 8_565 ?
C24 C24 1.489(4) 8_565 ?
C24 C25 1.394(3) . ?
C25 C26 1.386(4) . ?
C26 C27 1.385(3) . ?
C27 C26 1.385(3) 8_565 ?
O1 C1 1.305(3) . ?
O2 C1 1.220(3) . ?
C1 C2 1.502(3) . ?
C2 C3 1.386(3) . ?
C2 C5 1.391(3) . ?
C3 C4 1.382(3) . ?
C4 C3 1.382(3) 8_565 ?
C5 C2 1.391(3) 8_565 ?

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 N1 C6 116.6(2) . . ?
N1 C6 C7 123.4(2) . . ?
C6 C7 C8 120.2(2) . . ?
C7 C8 C11 121.0(2) . . ?
C9 C8 C7 115.8(2) . . ?
C9 C8 C11 123.1(2) . . ?
C10 C9 C8 120.5(2) . . ?
N1 C10 C9 123.5(2) . . ?
C12 C11 C8 124.1(2) . . ?
C12 C11 C13 107.5(2) . . ?
C13 C11 C8 128.2(2) . . ?
C11 C12 C11 111.1(3) . 8_575 ?
C11 C13 C13 107.01(12) . 8_575 ?
C14 C13 C11 126.2(2) . . ?
C14 C13 C13 126.73(14) . 8_575 ?
C15 C14 C13 129.4(2) . . ?
C16 C15 C14 129.1(3) . . ?
C15 C16 C15 129.1(3) . 8_575 ?
C21 N2 C17 115.6(2) . . ?
N2 C17 C18 124.3(3) . . ?
C19 C18 C17 119.7(2) . . ?
C18 C19 C20 116.3(2) . . ?
C18 C19 C22 121.0(2) . . ?
C20 C19 C22 122.7(2) . . ?
C21 C20 C19 119.8(3) . . ?
N2 C21 C20 124.3(3) . . ?
C23 C22 C19 126.0(2) . . ?
C23 C22 C24 107.5(2) . . ?
C24 C22 C19 126.5(2) . . ?
C22 C23 C22 111.0(3) . 8_565 ?
C22 C24 C24 106.93(13) . 8_565 ?
C25 C24 C22 125.9(2) . . ?
C25 C24 C24 126.94(15) . 8_565 ?
C26 C25 C24 129.4(3) . . ?
C27 C26 C25 128.7(3) . . ?
C26 C27 C26 129.8(4) . 8_565 ?
O1 C1 C2 114.5(2) . . ?
O2 C1 O1 124.0(2) . . ?
O2 C1 C2 121.5(2) . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 C5 119.6(2) . . ?
C5 C2 C1 121.5(2) . . ?
C4 C3 C2 120.6(2) . . ?
C3 C4 C3 119.6(3) . 8_565 ?
C2 C5 C2 120.0(3) . 8_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14 N2 0.93 2.68 3.378(3) 132.2 .
O1 H1 N1 0.82 1.80 2.623(2) 177.9 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shi_2460_sini
_database_code_depnum_ccdc_archive 'CCDC 1834436'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2018-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H6 O6, C20 H14 N2, 0.85(H2 O)'
_chemical_formula_sum            'C29 H21.70 N2 O6.85'
_chemical_formula_weight         507.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H30 N2 O6'
_chemical_oxdiff_usercomment     S_32
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   21.627(2)
_cell_length_b                   7.3399(7)
_cell_length_c                   20.281(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.943(7)
_cell_angle_gamma                90.00
_cell_volume                     2844.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2038
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7550
_cell_measurement_theta_min      2.1220
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1058
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1351
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4957
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.01
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   53.00   95.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127  178.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00   89.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127   19.0000 -180.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega   40.00   69.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.5127  178.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -81.00  -47.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1690 -178.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -47.00   -3.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       19.6690  -57.0000 -120.0000 44
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0266485000
_diffrn_orient_matrix_UB_12      -0.0629262000
_diffrn_orient_matrix_UB_13      0.0219094000
_diffrn_orient_matrix_UB_21      0.0097077000
_diffrn_orient_matrix_UB_22      0.0560169000
_diffrn_orient_matrix_UB_23      0.0318633000
_diffrn_orient_matrix_UB_31      -0.0239532000
_diffrn_orient_matrix_UB_32      -0.0473676000
_diffrn_orient_matrix_UB_33      0.0085094000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2450
_reflns_number_total             4957
_reflns_odcompleteness_completeness 97.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4957
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0821
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1072P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2523
_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. 
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.570(3)
 0.430(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Uiso/Uaniso restraints and constraints
C14 \\sim N1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Fixed Sof: O1W(0.15) H1WA(0.15) H1WB(0.15) O4W(0.05) H4WA(0.05) H4WB(0.05)
 O8W(0.1) H8WA(0.1) H8WB(0.1) O2W(0.15) H2WA(0.15) H2WB(0.15) O6W(0.15)
 H6WA(0.15) H6WB(0.15) O5W(0.05) H5WA(0.05) H5WB(0.05) O7W(0.1) H7WA(0.1)
 H7WB(0.1) O3W(0.1) H3WA(0.1) H3WB(0.1)
5.a Riding coordinates:
 O1(H1), O5(H5), O1W(H1WA,H1WB), O4W(H4WA,H4WB), O8W(H8WA,H8WB), O2W(H2WA,
 H2WB), O6W(H6WA,H6WB), O5W(H5WA,H5WB), O7W(H7WA,H7WB), O3W(H3WA,H3WB)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5A), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C29(H29), C30(H30), C28(H28), C27(H27), C24(H24), C23(H23), C22(H22), C21(H21),
  C20(H20)
5.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.6562(2) 0.8146(8) 0.5871(3) 0.088(2) Uani 1 d . . . .
H1 H 0.6126 0.8056 0.5585 0.132 Uiso 1 d . . R .
O2 O 0.6593(3) 0.7586(10) 0.6938(3) 0.100(2) Uani 1 d . . . .
O3 O 0.9615(2) 1.0671(7) 0.6775(2) 0.0561(12) Uani 1 d . . . .
H3 H 0.9740 1.1230 0.6508 0.084 Uiso 1 calc . . GR .
O4 O 0.8645(2) 1.0301(7) 0.5717(2) 0.0716(15) Uani 1 d . . . .
O5 O 0.9896(2) 0.7344(6) 0.9002(2) 0.0524(12) Uani 1 d . . . .
H5 H 1.0206 0.7227 0.9441 0.079 Uiso 1 d . . R .
O6 O 0.9024(2) 0.7748(8) 0.9260(2) 0.0680(15) Uani 1 d . . . .
C1 C 0.6882(3) 0.7989(10) 0.6582(5) 0.062(2) Uani 1 d . . . .
C2 C 0.7653(3) 0.8288(8) 0.6931(4) 0.0435(15) Uani 1 d . . . .
C3 C 0.8074(3) 0.7926(8) 0.7670(4) 0.0452(15) Uani 1 d . . . .
H3A H 0.7868 0.7530 0.7957 0.054 Uiso 1 calc . . R .
C4 C 0.8803(3) 0.8127(8) 0.8012(3) 0.0362(13) Uani 1 d . . . .
C5 C 0.9086(3) 0.8795(7) 0.7574(3) 0.0353(13) Uani 1 d . . . .
H5A H 0.9568 0.8928 0.7782 0.042 Uiso 1 calc . . R .
C6 C 0.8670(3) 0.9269(7) 0.6837(3) 0.0383(14) Uani 1 d . . . .
C7 C 0.7945(3) 0.8976(8) 0.6505(3) 0.0458(15) Uani 1 d . . . .
H7 H 0.7663 0.9242 0.6003 0.055 Uiso 1 calc . . R .
C8 C 0.8970(3) 1.0096(9) 0.6373(3) 0.0422(15) Uani 1 d . . . .
C9 C 0.9257(3) 0.7694(8) 0.8815(3) 0.0440(15) Uani 1 d . . . .
N1 N 0.5241(3) 0.7623(10) 0.5184(5) 0.083(2) Uani 1 d . . . U
N2 N 0.0647(3) 0.7053(8) 0.0452(3) 0.0542(15) Uani 1 d . . . .
C10 C 0.4958(4) 0.6979(13) 0.4481(5) 0.080(3) Uani 1 d . . . .
H10 H 0.5252 0.6734 0.4274 0.097 Uiso 1 calc . . R .
C11 C 0.4276(3) 0.6680(11) 0.4070(5) 0.071(2) Uani 1 d . . . .
H11 H 0.4112 0.6165 0.3599 0.086 Uiso 1 calc . . R .
C12 C 0.3799(3) 0.7123(9) 0.4332(4) 0.0540(18) Uani 1 d . . . .
C13 C 0.4076(3) 0.7833(11) 0.5050(4) 0.066(2) Uani 1 d . . . .
H13 H 0.3790 0.8166 0.5258 0.080 Uiso 1 calc . . R .
C14 C 0.4810(4) 0.8025(12) 0.5450(5) 0.086(3) Uani 1 d . . . U
H14 H 0.5001 0.8468 0.5936 0.103 Uiso 1 calc . . R .
C15 C 0.3056(3) 0.6806(9) 0.3866(3) 0.0478(17) Uani 1 d . . . .
C16 C 0.2712(3) 0.7049(9) 0.3090(3) 0.0478(17) Uani 1 d . . . .
H16 H 0.2932 0.7415 0.2813 0.057 Uiso 1 calc . . R .
C17 C 0.1996(3) 0.6671(8) 0.2784(3) 0.0421(15) Uani 1 d . . . .
C25 C 0.1863(3) 0.6082(8) 0.3373(3) 0.0427(15) Uani 1 d . . . .
C19 C 0.2549(3) 0.6176(9) 0.4065(3) 0.0485(16) Uani 1 d . . . .
C26 C 0.1510(3) 0.6828(8) 0.1986(3) 0.0415(15) Uani 1 d . . . .
C29 C 0.1770(3) 0.6605(10) 0.1467(4) 0.060(2) Uani 1 d . . . .
H29 H 0.2242 0.6355 0.1636 0.073 Uiso 1 calc . . R .
C30 C 0.1333(4) 0.6754(10) 0.0723(3) 0.0597(19) Uani 1 d . . . .
H30 H 0.1517 0.6645 0.0392 0.072 Uiso 1 calc . . R .
C28 C 0.0386(4) 0.7230(9) 0.0917(4) 0.0567(19) Uani 1 d . . . .
H28 H -0.0093 0.7414 0.0722 0.068 Uiso 1 calc . . R .
C27 C 0.0796(3) 0.7154(8) 0.1691(3) 0.0442(15) Uani 1 d . . . .
H27 H 0.0594 0.7317 0.2003 0.053 Uiso 1 calc . . R .
C24 C 0.1249(3) 0.5409(8) 0.3310(3) 0.0451(15) Uani 1 d . . . .
H24 H 0.0884 0.5331 0.2825 0.054 Uiso 1 calc . . R .
C23 C 0.1090(3) 0.4824(10) 0.3863(4) 0.0567(18) Uani 1 d . . . .
H23 H 0.0624 0.4509 0.3698 0.068 Uiso 1 calc . . R .
C22 C 0.1514(4) 0.4640(10) 0.4615(4) 0.064(2) Uani 1 d . . . .
H22 H 0.1298 0.4223 0.4890 0.076 Uiso 1 calc . . R .
C21 C 0.2228(4) 0.4998(11) 0.5021(4) 0.073(2) Uani 1 d . . . .
H21 H 0.2431 0.4734 0.5528 0.087 Uiso 1 calc . . R .
C20 C 0.2678(3) 0.5696(10) 0.4771(4) 0.0604(19) Uani 1 d . . . .
H20 H 0.3137 0.5864 0.5140 0.072 Uiso 1 calc . . R .
O1W O 0.2907(18) 1.012(5) 0.575(2) 0.079(11) Uiso 0.15 d A 2 . .
H1WA H 0.3065 1.0092 0.5438 0.118 Uiso 0.15 d A 2 R .
H1WB H 0.3193 1.0693 0.6140 0.118 Uiso 0.15 d A 2 R .
O4W O 0.421(7) 0.663(17) 0.699(7) 0.10(4) Uiso 0.05 d B 1 . .
H4WA H 0.3902 0.7460 0.6862 0.150 Uiso 0.05 d B 1 R .
H4WB H 0.4052 0.5653 0.7080 0.150 Uiso 0.05 d B 1 R .
O8W O 0.422(3) 0.529(7) 0.666(3) 0.075(14) Uiso 0.10 d C 4 . .
H8WA H 0.4403 0.5003 0.6379 0.112 Uiso 0.10 d C 4 R .
H8WB H 0.3884 0.6020 0.6425 0.112 Uiso 0.10 d C 4 R .
O2W O 0.309(3) 1.100(6) 0.608(3) 0.106(15) Uiso 0.15 d D 1 . .
H2WA H 0.2655 1.0824 0.5845 0.160 Uiso 0.15 d D 1 R .
H2WB H 0.3266 1.0822 0.5781 0.160 Uiso 0.15 d D 1 R .
O6W O 0.3418(17) 1.008(4) 0.6997(19) 0.074(9) Uiso 0.15 d E 4 . .
H6WA H 0.3241 1.0796 0.6626 0.111 Uiso 0.15 d E 4 R .
H6WB H 0.3352 1.0498 0.7349 0.111 Uiso 0.15 d E 4 R .
O5W O 0.452(7) 0.386(19) 0.736(8) 0.12(5) Uiso 0.05 d F 3 . .
H5WA H 0.4380 0.2784 0.7376 0.184 Uiso 0.05 d F 3 R .
H5WB H 0.4862 0.3828 0.7271 0.184 Uiso 0.05 d F 3 R .
O7W O 0.394(4) 0.554(11) 0.710(5) 0.14(3) Uiso 0.10 d G 2 . .
H7WA H 0.3591 0.5933 0.6711 0.215 Uiso 0.10 d G 2 R .
H7WB H 0.3793 0.4818 0.7331 0.215 Uiso 0.10 d G 2 R .
O3W O 0.355(5) 1.082(12) 0.646(5) 0.15(3) Uiso 0.10 d H 3 . .
H3WA H 0.3666 1.0906 0.6114 0.220 Uiso 0.10 d H 3 R .
H3WB H 0.3509 0.9698 0.6541 0.220 Uiso 0.10 d H 3 R .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.279(9) . ?
O2 C1 1.192(9) . ?
O3 C8 1.312(6) . ?
O4 C8 1.189(7) . ?
O5 C9 1.276(7) . ?
O6 C9 1.224(7) . ?
C1 C2 1.492(8) . ?
C2 C3 1.366(8) . ?
C2 C7 1.382(9) . ?
C3 C4 1.401(8) . ?
C4 C5 1.384(8) . ?
C4 C9 1.489(8) . ?
C5 C6 1.380(7) . ?
C6 C7 1.404(7) . ?
C6 C8 1.498(8) . ?
N1 C10 1.346(11) . ?
N1 C14 1.311(11) . ?
N2 C30 1.336(8) . ?
N2 C28 1.313(9) . ?
C10 C11 1.328(9) . ?
C11 C12 1.403(10) . ?
C12 C13 1.390(10) . ?
C12 C15 1.451(8) . ?
C13 C14 1.411(10) . ?
C15 C16 1.403(8) . ?
C15 C19 1.412(9) . ?
C16 C17 1.400(8) . ?
C17 C25 1.419(8) . ?
C17 C26 1.465(8) . ?
C25 C19 1.492(8) . ?
C25 C24 1.365(8) . ?
C19 C20 1.371(9) . ?
C26 C29 1.416(9) . ?
C26 C27 1.391(8) . ?
C29 C30 1.359(9) . ?
C28 C27 1.396(8) . ?
C24 C23 1.387(9) . ?
C23 C22 1.369(10) . ?
C22 C21 1.392(10) . ?
C21 C20 1.388(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 114.5(7) . . ?
O2 C1 O1 123.1(6) . . ?
O2 C1 C2 122.4(7) . . ?
C3 C2 C1 120.9(7) . . ?
C3 C2 C7 119.5(5) . . ?
C7 C2 C1 119.6(6) . . ?
C2 C3 C4 122.6(6) . . ?
C3 C4 C9 122.2(6) . . ?
C5 C4 C3 116.9(5) . . ?
C5 C4 C9 120.9(5) . . ?
C6 C5 C4 121.7(5) . . ?
C5 C6 C7 119.7(6) . . ?
C5 C6 C8 121.9(5) . . ?
C7 C6 C8 118.4(5) . . ?
C2 C7 C6 119.4(5) . . ?
O3 C8 C6 112.8(5) . . ?
O4 C8 O3 123.6(6) . . ?
O4 C8 C6 123.5(5) . . ?
O5 C9 C4 115.9(5) . . ?
O6 C9 O5 123.3(6) . . ?
O6 C9 C4 120.7(6) . . ?
C14 N1 C10 117.1(6) . . ?
C28 N2 C30 119.3(5) . . ?
C11 C10 N1 123.0(9) . . ?
C10 C11 C12 121.4(9) . . ?
C11 C12 C15 120.2(6) . . ?
C13 C12 C11 116.8(6) . . ?
C13 C12 C15 123.0(7) . . ?
C12 C13 C14 117.2(8) . . ?
N1 C14 C13 124.5(8) . . ?
C16 C15 C12 123.6(6) . . ?
C16 C15 C19 106.7(5) . . ?
C19 C15 C12 129.6(6) . . ?
C17 C16 C15 111.5(6) . . ?
C16 C17 C25 107.8(5) . . ?
C16 C17 C26 123.1(6) . . ?
C25 C17 C26 129.1(5) . . ?
C17 C25 C19 105.9(5) . . ?
C24 C25 C17 127.1(5) . . ?
C24 C25 C19 126.8(6) . . ?
C15 C19 C25 108.0(5) . . ?
C20 C19 C15 125.3(6) . . ?
C20 C19 C25 126.7(6) . . ?
C29 C26 C17 118.9(5) . . ?
C27 C26 C17 124.5(6) . . ?
C27 C26 C29 116.6(5) . . ?
C30 C29 C26 120.3(6) . . ?
N2 C30 C29 122.0(7) . . ?
N2 C28 C27 122.9(6) . . ?
C26 C27 C28 118.9(6) . . ?
C25 C24 C23 129.5(6) . . ?
C22 C23 C24 129.9(6) . . ?
C23 C22 C21 128.2(7) . . ?
C20 C21 C22 128.8(7) . . ?
C19 C20 C21 129.9(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.85 1.72 2.554(7) 166.5 .
O3 H3 O5 0.82 1.77 2.583(6) 173.6 2_756
O5 H5 N2 0.83 1.81 2.617(6) 162.0 1_656
C30 H30 O4 0.93 2.33 3.129(8) 144.3 2_645
C22 H22 O6 0.93 2.40 3.313(9) 167.1 2_646

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.570(3)
2 0.430(3)

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

data_shi_1454_seio
_database_code_depnum_ccdc_archive 'CCDC 1834420'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H14 N2, C12 H10 O2'
_chemical_formula_sum            'C32 H24 N2 O2'
_chemical_formula_weight         468.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H20 N2 O2'
_chemical_oxdiff_usercomment     'S_8, 0.8x0.2x0.15, maro-verzi'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   7.1365(9)
_cell_length_b                   22.3829(14)
_cell_length_c                   30.1328(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4813.3(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1597
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      29.5919
_cell_measurement_theta_min      2.6981
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0930
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            12841
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00   18.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.9352  -99.0000  -91.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   82.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.7477   57.0000  -90.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   63.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       16.7477  178.0000   90.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0522389000
_diffrn_orient_matrix_UB_12      0.0234013000
_diffrn_orient_matrix_UB_13      -0.0099629000
_diffrn_orient_matrix_UB_21      -0.0800187000
_diffrn_orient_matrix_UB_22      -0.0187686000
_diffrn_orient_matrix_UB_23      -0.0008436000
_diffrn_orient_matrix_UB_31      -0.0275301000
_diffrn_orient_matrix_UB_32      0.0101924000
_diffrn_orient_matrix_UB_33      0.0213050000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2526
_reflns_number_total             4253
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0342P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1224
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A), O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1 N 0.6920(4) 0.60132(10) 0.30193(8) 0.0542(7) Uani 1 d . . .
N2 N 0.7044(3) 1.00680(9) 0.45085(8) 0.0384(6) Uani 1 d . . .
C1 C 0.5781(4) 0.63187(12) 0.32860(10) 0.0505(8) Uani 1 d . . .
H1 H 0.4958 0.6104 0.3464 0.061 Uiso 1 calc . . R
C2 C 0.5743(4) 0.69360(12) 0.33143(9) 0.0416(7) Uani 1 d . . .
H2 H 0.4916 0.7122 0.3509 0.050 Uiso 1 calc . . R
C3 C 0.6941(4) 0.72792(11) 0.30528(8) 0.0334(6) Uani 1 d . . .
C4 C 0.8152(4) 0.69592(12) 0.27816(9) 0.0425(7) Uani 1 d . . .
H4 H 0.9007 0.7161 0.2603 0.051 Uiso 1 calc . . R
C5 C 0.8091(4) 0.63389(13) 0.27759(10) 0.0513(8) Uani 1 d . . .
H5 H 0.8920 0.6139 0.2590 0.062 Uiso 1 calc . . R
C6 C 0.6921(3) 0.79325(11) 0.30792(8) 0.0315(6) Uani 1 d . . .
C7 C 0.6762(3) 0.82480(11) 0.34758(8) 0.0327(7) Uani 1 d . . .
H7 H 0.6647 0.8071 0.3754 0.039 Uiso 1 calc . . R
C8 C 0.6796(3) 0.88661(11) 0.34034(8) 0.0313(6) Uani 1 d . . .
C9 C 0.6925(3) 0.89568(11) 0.29376(8) 0.0309(6) Uani 1 d . . .
C10 C 0.6817(4) 0.95016(11) 0.27167(9) 0.0386(7) Uani 1 d . . .
H10 H 0.6667 0.9834 0.2898 0.046 Uiso 1 calc . . R
C11 C 0.6899(4) 0.96205(13) 0.22649(10) 0.0470(8) Uani 1 d . . .
H11 H 0.6819 1.0022 0.2188 0.056 Uiso 1 calc . . R
C12 C 0.7083(4) 0.92315(13) 0.19138(9) 0.0464(8) Uani 1 d . . .
H12 H 0.7172 0.9408 0.1635 0.056 Uiso 1 calc . . R
C13 C 0.7152(4) 0.86142(12) 0.19188(9) 0.0433(7) Uani 1 d . . .
H13 H 0.7247 0.8432 0.1642 0.052 Uiso 1 calc . . R
C14 C 0.7099(4) 0.82279(12) 0.22789(9) 0.0382(7) Uani 1 d . . .
H14 H 0.7118 0.7824 0.2208 0.046 Uiso 1 calc . . R
C15 C 0.7023(3) 0.83559(11) 0.27286(8) 0.0319(6) Uani 1 d . . .
C16 C 0.6801(3) 0.93051(11) 0.37638(8) 0.0308(6) Uani 1 d . . .
C17 C 0.7710(4) 0.98556(11) 0.37412(9) 0.0367(7) Uani 1 d . . .
H17 H 0.8267 0.9981 0.3478 0.044 Uiso 1 calc . . R
C18 C 0.7774(4) 1.02126(11) 0.41142(9) 0.0395(7) Uani 1 d . . .
H18 H 0.8368 1.0581 0.4090 0.047 Uiso 1 calc . . R
C19 C 0.5984(3) 0.91603(11) 0.41698(8) 0.0334(7) Uani 1 d . . .
H19 H 0.5325 0.8804 0.4200 0.040 Uiso 1 calc . . R
C20 C 0.6149(4) 0.95422(11) 0.45264(9) 0.0379(7) Uani 1 d . . .
H20 H 0.5609 0.9429 0.4794 0.046 Uiso 1 calc . . R
O1 O 0.2309(3) 0.52115(7) 0.40122(6) 0.0433(5) Uani 1 d . . .
H1A H 0.2732 0.5012 0.4218 0.065 Uiso 1 calc . . GR
O2 O 0.1628(2) 0.95068(6) 0.47371(6) 0.0365(5) Uani 1 d . . .
H2A H 0.2130 0.9588 0.4974 0.055 Uiso 1 calc . . GR
C21 C 0.2196(4) 0.58009(10) 0.41391(8) 0.0317(6) Uani 1 d . . .
C22 C 0.1180(4) 0.61848(11) 0.38754(9) 0.0454(8) Uani 1 d . . .
H22 H 0.0566 0.6041 0.3625 0.055 Uiso 1 calc . . R
C23 C 0.1075(4) 0.67853(11) 0.39841(9) 0.0451(8) Uani 1 d . . .
H23 H 0.0383 0.7039 0.3803 0.054 Uiso 1 calc . . R
C24 C 0.1968(3) 0.70212(10) 0.43543(8) 0.0278(6) Uani 1 d . . .
C25 C 0.2962(3) 0.66204(10) 0.46138(8) 0.0339(7) Uani 1 d . . .
H25 H 0.3566 0.6760 0.4867 0.041 Uiso 1 calc . . R
C26 C 0.3087(3) 0.60183(10) 0.45084(8) 0.0345(7) Uani 1 d . . .
H26 H 0.3777 0.5762 0.4688 0.041 Uiso 1 calc . . R
C27 C 0.1879(3) 0.76702(9) 0.44659(8) 0.0251(6) Uani 1 d . . .
C28 C 0.0919(3) 0.80756(10) 0.41990(8) 0.0325(6) Uani 1 d . . .
H28 H 0.0304 0.7935 0.3948 0.039 Uiso 1 calc . . R
C29 C 0.0846(4) 0.86801(10) 0.42929(8) 0.0332(7) Uani 1 d . . .
H29 H 0.0199 0.8937 0.4105 0.040 Uiso 1 calc . . R
C30 C 0.1732(3) 0.89017(10) 0.46652(8) 0.0283(6) Uani 1 d . . .
C31 C 0.2692(4) 0.85143(10) 0.49412(9) 0.0359(7) Uani 1 d . . .
H31 H 0.3287 0.8658 0.5194 0.043 Uiso 1 calc . . R
C32 C 0.2762(4) 0.79104(10) 0.48395(9) 0.0364(7) Uani 1 d . . .
H32 H 0.3422 0.7656 0.5027 0.044 Uiso 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 C1 1.332(3) . ?
N1 C5 1.329(3) . ?
N2 C18 1.337(3) . ?
N2 C20 1.340(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.388(3) . ?
C3 C6 1.465(3) . ?
C4 C5 1.389(3) . ?
C6 C7 1.393(3) . ?
C6 C15 1.421(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.421(3) . ?
C8 C16 1.465(3) . ?
C9 C10 1.391(3) . ?
C9 C15 1.487(3) . ?
C10 C11 1.389(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.383(3) . ?
C13 C14 1.388(3) . ?
C14 C15 1.386(3) . ?
C16 C17 1.394(3) . ?
C16 C19 1.394(3) . ?
C17 C18 1.380(3) . ?
C19 C20 1.378(3) . ?
O1 C21 1.376(3) . ?
O2 C30 1.374(2) . ?
C21 C22 1.377(3) . ?
C21 C26 1.371(3) . ?
C22 C23 1.385(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.386(3) . ?
C24 C27 1.492(3) . ?
C25 C26 1.388(3) . ?
C27 C28 1.393(3) . ?
C27 C32 1.398(3) . ?
C28 C29 1.383(3) . ?
C29 C30 1.380(3) . ?
C30 C31 1.383(3) . ?
C31 C32 1.387(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
C5 N1 C1 115.8(2) . . ?
C18 N2 C20 115.7(2) . . ?
N1 C1 C2 124.1(3) . . ?
C1 C2 C3 120.2(3) . . ?
C2 C3 C6 120.9(2) . . ?
C4 C3 C2 115.5(2) . . ?
C4 C3 C6 123.6(2) . . ?
C3 C4 C5 120.2(3) . . ?
N1 C5 C4 124.1(3) . . ?
C7 C6 C3 123.6(2) . . ?
C7 C6 C15 107.7(2) . . ?
C15 C6 C3 128.7(2) . . ?
C6 C7 C8 111.5(2) . . ?
C7 C8 C9 107.2(2) . . ?
C7 C8 C16 123.2(2) . . ?
C9 C8 C16 129.5(2) . . ?
C8 C9 C15 107.0(2) . . ?
C10 C9 C8 126.4(2) . . ?
C10 C9 C15 126.4(2) . . ?
C11 C10 C9 129.4(3) . . ?
C12 C11 C10 129.5(3) . . ?
C11 C12 C13 128.8(3) . . ?
C12 C13 C14 129.1(3) . . ?
C15 C14 C13 129.5(3) . . ?
C6 C15 C9 106.6(2) . . ?
C14 C15 C6 126.2(2) . . ?
C14 C15 C9 127.1(2) . . ?
C17 C16 C8 123.9(2) . . ?
C19 C16 C8 119.6(2) . . ?
C19 C16 C17 116.3(2) . . ?
C18 C17 C16 119.2(2) . . ?
N2 C18 C17 124.8(2) . . ?
C20 C19 C16 120.3(2) . . ?
N2 C20 C19 123.7(3) . . ?
O1 C21 C22 118.0(2) . . ?
C26 C21 O1 122.6(2) . . ?
C26 C21 C22 119.4(2) . . ?
C21 C22 C23 119.8(2) . . ?
C22 C23 C24 122.3(2) . . ?
C23 C24 C27 122.1(2) . . ?
C25 C24 C23 116.2(2) . . ?
C25 C24 C27 121.7(2) . . ?
C24 C25 C26 122.2(2) . . ?
C21 C26 C25 120.1(2) . . ?
C28 C27 C24 121.7(2) . . ?
C28 C27 C32 115.9(2) . . ?
C32 C27 C24 122.4(2) . . ?
C29 C28 C27 122.5(2) . . ?
C30 C29 C28 120.0(2) . . ?
O2 C30 C29 117.2(2) . . ?
O2 C30 C31 123.4(2) . . ?
C29 C30 C31 119.4(2) . . ?
C30 C31 C32 119.8(2) . . ?
C31 C32 C27 122.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.82 1.98 2.799(2) 171.7 7_655
O2 H2A N2 0.82 1.84 2.641(3) 166.8 5_676

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1834733'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H25.50 N2.50 O7'
_chemical_formula_weight         545.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        Pnca
_space_group_name_Hall           '-P 2a 2n'

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

_cell_length_a                   13.1102(5)
_cell_length_b                   14.3955(6)
_cell_length_c                   30.2012(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5699.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23175
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      31.52

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             2280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE-IPDS II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56098
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5587
_reflns_number_gt                3618
_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       X-Area
_computing_cell_refinement       X-Area
_computing_data_reduction        X-Area
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1414P)²+0.8289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0087(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5587
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.2262
_refine_ls_wR_factor_gt          0.1947
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0915(2) 0.2045(2) 0.13253(10) 0.0632(8) Uani 1 1 d . . . . .
H1 H 1.0643 0.2298 0.1068 0.076 Uiso 1 1 calc R U . . .
C2 C 1.1927(2) 0.1823(2) 0.13395(10) 0.0600(7) Uani 1 1 d . . . . .
H2 H 1.2340 0.1945 0.1096 0.072 Uiso 1 1 calc R U . . .
C3 C 1.23438(19) 0.14157(19) 0.17171(9) 0.0533(6) Uani 1 1 d . . . . .
C4 C 1.1690(2) 0.1287(2) 0.20777(10) 0.0572(7) Uani 1 1 d . . . . .
H4 H 1.1938 0.1026 0.2338 0.069 Uiso 1 1 calc R U . . .
C5 C 1.0691(2) 0.1540(2) 0.20501(10) 0.0603(7) Uani 1 1 d . . . . .
H5 H 1.0266 0.1461 0.2294 0.072 Uiso 1 1 calc R U . . .
C6 C 1.34155(19) 0.11433(19) 0.17442(10) 0.0545(6) Uani 1 1 d . . . . .
C7 C 1.40023(19) 0.12014(19) 0.21316(10) 0.0558(7) Uani 1 1 d . . . . .
H7 H 1.3758 0.1396 0.2405 0.067 Uiso 1 1 calc R U . . .
C8 C 1.50005(18) 0.09273(19) 0.20481(10) 0.0542(7) Uani 1 1 d . . . . .
C9 C 1.58263(18) 0.09750(19) 0.23771(11) 0.0560(7) Uani 1 1 d . . . . .
C10 C 1.5644(2) 0.0766(2) 0.28171(11) 0.0637(8) Uani 1 1 d . . . . .
H10 H 1.5004 0.0559 0.2906 0.076 Uiso 1 1 calc R U . . .
C11 C 1.6407(2) 0.0864(2) 0.31213(12) 0.0702(8) Uani 1 1 d . . . . .
H11 H 1.6262 0.0735 0.3416 0.084 Uiso 1 1 calc R U . . .
C12 C 1.7532(2) 0.1328(2) 0.25961(12) 0.0655(8) Uani 1 1 d . . . . .
H12 H 1.8185 0.1521 0.2519 0.079 Uiso 1 1 calc R U . . .
C13 C 1.6813(2) 0.1258(2) 0.22680(11) 0.0604(7) Uani 1 1 d . . . . .
H13 H 1.6980 0.1398 0.1976 0.072 Uiso 1 1 calc R U . . .
C14 C 1.50604(19) 0.06331(19) 0.16039(10) 0.0567(7) Uani 1 1 d . . . . .
C15 C 1.5900(2) 0.0217(2) 0.14034(12) 0.0681(8) Uani 1 1 d . . . . .
H15 H 1.6475 0.0160 0.1582 0.082 Uiso 1 1 calc R U . . .
C16 C 1.6004(3) -0.0124(3) 0.09784(15) 0.0825(10) Uani 1 1 d . . . . .
H16 H 1.6646 -0.0357 0.0908 0.099 Uiso 1 1 calc R U . . .
C17 C 1.5296(3) -0.0165(3) 0.06478(14) 0.0879(11) Uani 1 1 d . . . . .
H17 H 1.5524 -0.0427 0.0384 0.106 Uiso 1 1 calc R U . . .
C18 C 1.4282(3) 0.0127(3) 0.06472(12) 0.0837(11) Uani 1 1 d . . . . .
H18 H 1.3925 0.0033 0.0385 0.100 Uiso 1 1 calc R U . . .
C19 C 1.3745(2) 0.0537(2) 0.09854(11) 0.0686(8) Uani 1 1 d . . . . .
H19 H 1.3069 0.0672 0.0918 0.082 Uiso 1 1 calc R U . . .
C20 C 1.40403(19) 0.07802(19) 0.14049(10) 0.0550(7) Uani 1 1 d . . . . .
C21 C 0.81928(19) 0.2400(2) 0.11634(9) 0.0552(7) Uani 1 1 d . . . . .
C22 C 0.70934(18) 0.25423(18) 0.10357(9) 0.0489(6) Uani 1 1 d . . . . .
C23 C 0.6778(2) 0.23863(19) 0.06050(9) 0.0535(6) Uani 1 1 d . . . . .
H23 H 0.7251 0.2197 0.0394 0.064 Uiso 1 1 calc R U . . .
C24 C 0.5764(2) 0.2509(2) 0.04836(9) 0.0547(7) Uani 1 1 d . . . . .
C25 C 0.5449(2) 0.2339(3) 0.00204(10) 0.0674(8) Uani 1 1 d . . . . .
C26 C 0.50665(19) 0.28086(19) 0.07982(9) 0.0540(7) Uani 1 1 d . . . . .
H26 H 0.4387 0.2893 0.0719 0.065 Uiso 1 1 calc R U . . .
C27 C 0.53751(18) 0.29832(18) 0.12295(9) 0.0481(6) Uani 1 1 d . . . . .
C28 C 0.46347(19) 0.3321(2) 0.15653(10) 0.0537(6) Uani 1 1 d . . . . .
C29 C 0.63866(18) 0.28421(18) 0.13475(9) 0.0477(6) Uani 1 1 d . . . . .
H29 H 0.6593 0.2949 0.1638 0.057 Uiso 1 1 calc R U . . .
C31 C 0.7500 0.5000 0.1662(4) 0.313(14) Uani 1 2 d S T P . .
C32 C 0.8291(9) 0.4844(6) 0.0998(5) 0.350(10) Uani 1 1 d . . . . .
H32A H 0.8064 0.4889 0.0697 0.525 Uiso 1 1 calc R U . . .
H32B H 0.8813 0.5299 0.1051 0.525 Uiso 1 1 calc R U . . .
H32C H 0.8560 0.4234 0.1051 0.525 Uiso 1 1 calc R U . . .
C33 C 0.2410(15) 0.4114(10) 0.0434(6) 0.214(10) Uani 0.5 1 d . . P . .
N1 N 1.03095(17) 0.19049(18) 0.16738(8) 0.0596(6) Uani 1 1 d . . . . .
N2 N 1.73470(18) 0.11366(19) 0.30169(10) 0.0671(7) Uani 1 1 d . . . . .
N3 N 0.7500 0.5000 0.1272(2) 0.123(2) Uani 1 2 d S T P . .
O1 O 0.83842(14) 0.23109(18) 0.15690(7) 0.0745(7) Uani 1 1 d . . . . .
O2 O 0.88488(15) 0.23781(19) 0.08687(7) 0.0776(7) Uani 1 1 d . . . . .
O3 O 0.60247(19) 0.2089(2) -0.02661(9) 0.0982(9) Uani 1 1 d . . . . .
O4 O 0.44725(17) 0.2473(2) -0.00507(8) 0.0912(9) Uani 1 1 d . . . . .
H4A H 0.4341 0.2361 -0.0311 0.137 Uiso 1 1 calc R U . . .
O5 O 0.37288(14) 0.34877(19) 0.14031(7) 0.0754(7) Uani 1 1 d . . . . .
H5A H 0.3353 0.3675 0.1601 0.113 Uiso 1 1 calc R U . . .
O6 O 0.48605(16) 0.34397(18) 0.19484(7) 0.0753(7) Uani 1 1 d . . . . .
O7 O 0.7896(6) 0.4833(7) 0.1996(3) 0.137(3) Uani 0.5 1 d . . P . .
O9 O 0.2500 0.5000 0.0388(3) 0.478(16) Uani 1 2 d S T P . .
H1N H 0.950(3) 0.204(3) 0.1629(13) 0.094(11) 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
C1 N1 1.334(4) . ?
C1 C2 1.365(4) . ?
C2 C3 1.394(4) . ?
C3 C4 1.399(4) . ?
C3 C6 1.461(3) . ?
C4 C5 1.362(4) . ?
C5 N1 1.348(4) . ?
C6 C7 1.403(4) . ?
C6 C20 1.412(4) . ?
C7 C8 1.390(4) . ?
C8 C14 1.409(4) . ?
C8 C9 1.471(4) . ?
C9 C10 1.383(5) . ?
C9 C13 1.395(4) . ?
C10 C11 1.365(4) . ?
C11 N2 1.331(4) . ?
C12 N2 1.323(4) . ?
C12 C13 1.371(4) . ?
C14 C15 1.392(4) . ?
C14 C20 1.481(4) . ?
C15 C16 1.381(5) . ?
C16 C17 1.365(6) . ?
C17 C18 1.395(5) . ?
C18 C19 1.374(5) . ?
C19 C20 1.370(4) . ?
C21 O2 1.238(3) . ?
C21 O1 1.257(3) . ?
C21 C22 1.506(3) . ?
C22 C23 1.383(4) . ?
C22 C29 1.390(4) . ?
C23 C24 1.390(4) . ?
C24 C26 1.388(4) . ?
C24 C25 1.479(4) . ?
C25 O3 1.203(4) . ?
C25 O4 1.313(4) . ?
C26 C27 1.387(4) . ?
C27 C29 1.388(3) . ?
C27 C28 1.486(4) . ?
C28 O6 1.206(3) . ?
C28 O5 1.307(3) . ?
C31 O7 1.159(11) . ?
C31 O7 1.159(11) 2_665 ?
C31 N3 1.177(13) . ?
C32 N3 1.345(8) . ?
C33 O9 1.289(14) . ?
N3 C32 1.345(8) 2_665 ?
O7 O7 1.145(15) 2_665 ?
O9 C33 1.289(14) 2_565 ?

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
N1 C1 C2 121.2(3) . . ?
C1 C2 C3 120.3(3) . . ?
C2 C3 C4 116.9(2) . . ?
C2 C3 C6 122.4(3) . . ?
C4 C3 C6 120.7(3) . . ?
C5 C4 C3 120.4(3) . . ?
N1 C5 C4 120.8(3) . . ?
C7 C6 C20 108.0(2) . . ?
C7 C6 C3 123.9(3) . . ?
C20 C6 C3 128.1(3) . . ?
C8 C7 C6 110.4(3) . . ?
C7 C8 C14 108.1(2) . . ?
C7 C8 C9 123.9(3) . . ?
C14 C8 C9 128.0(2) . . ?
C10 C9 C13 116.7(3) . . ?
C10 C9 C8 120.8(3) . . ?
C13 C9 C8 122.4(3) . . ?
C11 C10 C9 119.9(3) . . ?
N2 C11 C10 123.3(3) . . ?
N2 C12 C13 123.6(3) . . ?
C12 C13 C9 119.2(3) . . ?
C15 C14 C8 126.0(3) . . ?
C15 C14 C20 126.8(3) . . ?
C8 C14 C20 107.0(2) . . ?
C16 C15 C14 129.5(3) . . ?
C17 C16 C15 128.9(3) . . ?
C16 C17 C18 129.5(3) . . ?
C19 C18 C17 128.1(3) . . ?
C20 C19 C18 130.7(3) . . ?
C19 C20 C6 127.0(3) . . ?
C19 C20 C14 126.4(3) . . ?
C6 C20 C14 106.4(2) . . ?
O2 C21 O1 124.0(2) . . ?
O2 C21 C22 118.9(2) . . ?
O1 C21 C22 117.0(2) . . ?
C23 C22 C29 119.2(2) . . ?
C23 C22 C21 120.3(2) . . ?
C29 C22 C21 120.4(2) . . ?
C22 C23 C24 120.9(2) . . ?
C26 C24 C23 119.3(3) . . ?
C26 C24 C25 121.0(2) . . ?
C23 C24 C25 119.7(3) . . ?
O3 C25 O4 122.6(3) . . ?
O3 C25 C24 123.7(3) . . ?
O4 C25 C24 113.7(3) . . ?
C27 C26 C24 120.5(2) . . ?
C26 C27 C29 119.6(2) . . ?
C26 C27 C28 120.7(2) . . ?
C29 C27 C28 119.8(2) . . ?
O6 C28 O5 123.8(3) . . ?
O6 C28 C27 122.7(2) . . ?
O5 C28 C27 113.5(2) . . ?
C27 C29 C22 120.5(2) . . ?
O7 C31 O7 59.2(9) . 2_665 ?
O7 C31 N3 150.4(5) . . ?
O7 C31 N3 150.4(5) 2_665 . ?
C1 N1 C5 120.2(2) . . ?
C12 N2 C11 117.3(3) . . ?
C31 N3 C32 128.0(7) . 2_665 ?
C31 N3 C32 128.0(7) . . ?
C32 N3 C32 104.1(15) 2_665 . ?
O7 O7 C31 60.4(5) 2_665 . ?
C33 O9 C33 167.6(18) 2_565 . ?

_refine_diff_density_max         0.549
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.108

_shelxl_version_number           2014-3

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

data_shi_1586_nica
_database_code_depnum_ccdc_archive 'CCDC 1834427'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-07-05 downloaded from the CCDC.
;
_audit_creation_date             2018-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         
'2(C20 H14 N2), 2(C14 H10 O5), 2(C2 H3 N), 0.75(H2 O)'
_chemical_formula_sum            'C72 H55.50 N6 O10.75'
_chemical_formula_weight         1176.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 O4 N2'
_chemical_oxdiff_usercomment     'S_17, rosu-brun?, 0.4x0.2x0.1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   52.2362(18)
_cell_length_b                   7.4175(3)
_cell_length_c                   32.1601(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.831(4)
_cell_angle_gamma                90.00
_cell_volume                     12045.6(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8136
_cell_measurement_temperature    200.05(10)
_cell_measurement_theta_max      28.8196
_cell_measurement_theta_min      2.3349
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4924
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_limit_h_max       62
_diffrn_reflns_limit_h_min       -62
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            48203
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.42
_diffrn_ambient_temperature      200.05(10)
_diffrn_detector_area_resol_mean 16.1593
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   16.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  -99.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00  -35.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563 -178.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00   -4.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  -57.0000  150.0000 106

#__ type_ start__ end____ width___ exp.time_
  4 omega   25.00   95.50   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4563   19.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega  -90.00    3.00   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  -57.0000   60.0000 124

#__ type_ start__ end____ width___ exp.time_
  6 omega  -99.00  -36.00   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563 -178.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega -102.00  -51.75   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.9563  178.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
  8 omega  -48.00   45.00   0.7500   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.4563  -57.0000 -180.0000 124
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0132568000
_diffrn_orient_matrix_UB_12      0.0183832000
_diffrn_orient_matrix_UB_13      0.0004277000
_diffrn_orient_matrix_UB_21      0.0037509000
_diffrn_orient_matrix_UB_22      0.0883335000
_diffrn_orient_matrix_UB_23      0.0075949000
_diffrn_orient_matrix_UB_31      -0.0027561000
_diffrn_orient_matrix_UB_32      0.0315967000
_diffrn_orient_matrix_UB_33      -0.0215100000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7633
_reflns_number_total             10638
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     926
_refine_ls_number_reflns         10638
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0655
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0862P)²+14.8588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.1859
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 N3-C5 \\sim N2-C3 \\sim N1-C1
 with sigma of 0.001
 C3-C4 \\sim C2-C1 \\sim C6-C5
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uiso(N3) = Uiso(N2)
Uiso(C4) = Uiso(C6) = Uiso(C5) = Uiso(C3)
4. Others
 Fixed Sof: N2(0.75) C3(0.75) C4(0.75) H4C(0.75) H4D(0.75) H4E(0.75) N3(0.25)
 C5(0.25) C6(0.25) H6C(0.25) H6D(0.25) H6E(0.25) O2W(0.5) H2WA(0.5) H2WB(0.5)
 O1W(0.25) H1WA(0.25) H1WB(0.25)
5.a Riding coordinates:
 O1B(H1B), O4B(H4B), O4A(H4A), O1A(H1A), C4(H4C,H4D,H4E), C2(H2A,H2B,H2C),
 C6(H6C,H6D,H6E), O2W(H2WA,H2WB), O1W(H1WA,H1WB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
N1B N 0.02014(6) 0.9627(4) 0.42067(11) 0.0553(8) Uani 1 d . . .
N2B N 0.21190(5) 0.9423(4) 0.41240(8) 0.0380(6) Uani 1 d . . .
C15B C 0.03596(7) 1.0096(5) 0.39583(14) 0.0519(9) Uani 1 d . . .
H15B H 0.0289(7) 1.032(5) 0.3655(12) 0.062 Uiso 1 d . . R
C16B C 0.06281(6) 1.0314(5) 0.41184(12) 0.0435(8) Uani 1 d . . .
H16B H 0.0732(7) 1.072(5) 0.3932(11) 0.052 Uiso 1 d . . R
C17B C 0.07461(6) 1.0023(4) 0.45541(10) 0.0363(7) Uani 1 d . . .
C18B C 0.05780(6) 0.9493(5) 0.48061(13) 0.0455(8) Uani 1 d . . .
H18B H 0.0647(7) 0.931(5) 0.5113(12) 0.055 Uiso 1 d . . R
C19B C 0.03097(7) 0.9332(5) 0.46237(15) 0.0565(10) Uani 1 d . . .
H19B H 0.0173(8) 0.893(5) 0.4801(12) 0.068 Uiso 1 d . . R
C20B C 0.10347(6) 1.0208(4) 0.47167(10) 0.0324(7) Uani 1 d . . .
C21B C 0.12080(6) 0.9843(4) 0.44589(10) 0.0320(7) Uani 1 d . . .
H21B H 0.1155(6) 0.943(4) 0.4168(10) 0.038 Uiso 1 d . . R
C22B C 0.14706(5) 1.0098(4) 0.46886(9) 0.0285(6) Uani 1 d . . .
C23B C 0.14701(5) 1.0694(4) 0.51068(9) 0.0288(6) Uani 1 d . . .
C24B C 0.11880(6) 1.0748(4) 0.51243(9) 0.0324(7) Uani 1 d . . .
C25B C 0.10948(7) 1.1305(4) 0.54738(11) 0.0399(8) Uani 1 d . . .
H25B H 0.0902(7) 1.127(4) 0.5428(10) 0.048 Uiso 1 d . . R
C26B C 0.12364(8) 1.1898(4) 0.58775(11) 0.0455(8) Uani 1 d . . .
H26B H 0.1128(7) 1.212(5) 0.6097(11) 0.055 Uiso 1 d . . R
C27B C 0.15053(8) 1.2211(4) 0.60295(11) 0.0461(9) Uani 1 d . . .
H27B H 0.1559(7) 1.268(5) 0.6322(11) 0.055 Uiso 1 d . . R
C28B C 0.17061(7) 1.1991(4) 0.58237(11) 0.0430(8) Uani 1 d . . .
H28B H 0.1875(7) 1.236(5) 0.5986(11) 0.052 Uiso 1 d . . R
C29B C 0.16887(6) 1.1310(4) 0.54162(10) 0.0357(7) Uani 1 d . . .
H29B H 0.1860(6) 1.127(4) 0.5330(10) 0.043 Uiso 1 d . . R
C30B C 0.16975(5) 0.9836(4) 0.45044(9) 0.0290(6) Uani 1 d . . .
C31B C 0.16812(6) 1.0440(4) 0.40900(9) 0.0327(7) Uani 1 d . . .
H31B H 0.1520(6) 1.107(4) 0.3928(9) 0.039 Uiso 1 d . . R
C32B C 0.18912(6) 1.0210(4) 0.39109(11) 0.0380(7) Uani 1 d . . .
H32B H 0.1885(6) 1.066(4) 0.3615(10) 0.046 Uiso 1 d . . R
C33B C 0.19315(6) 0.8995(4) 0.47212(10) 0.0336(7) Uani 1 d . . .
H33B H 0.1946(6) 0.855(4) 0.4999(10) 0.040 Uiso 1 d . . R
C34B C 0.21338(6) 0.8833(4) 0.45216(10) 0.0367(7) Uani 1 d . . .
H34B H 0.2304(6) 0.823(4) 0.4655(10) 0.044 Uiso 1 d . . R
N1A N -0.00765(5) 1.5677(4) 0.34238(9) 0.0444(7) Uani 1 d . . .
N2A N 0.18257(5) 1.3957(3) 0.31376(8) 0.0347(6) Uani 1 d . . .
C15A C 0.00790(7) 1.6333(5) 0.31870(11) 0.0476(9) Uani 1 d . . .
H15A H -0.0009(7) 1.694(5) 0.2936(12) 0.057 Uiso 1 d . . R
C16A C 0.03510(6) 1.6215(5) 0.33074(10) 0.0398(8) Uani 1 d . . .
H16A H 0.0445(6) 1.679(4) 0.3105(10) 0.048 Uiso 1 d . . R
C17A C 0.04764(5) 1.5360(4) 0.36915(9) 0.0307(7) Uani 1 d . . .
C18A C 0.03132(6) 1.4669(4) 0.39347(11) 0.0374(7) Uani 1 d . . .
H18A H 0.0385(6) 1.398(4) 0.4195(10) 0.045 Uiso 1 d . . R
C19A C 0.00429(6) 1.4864(5) 0.37935(11) 0.0415(8) Uani 1 d . . .
H19A H -0.0085(7) 1.442(4) 0.3960(10) 0.050 Uiso 1 d . . R
C20A C 0.07685(5) 1.5191(4) 0.38156(9) 0.0291(6) Uani 1 d . . .
C21A C 0.09232(6) 1.4997(4) 0.35212(10) 0.0313(7) Uani 1 d . . .
H21A H 0.0851(6) 1.491(4) 0.3200(10) 0.038 Uiso 1 d . . R
C22A C 0.11920(5) 1.4918(4) 0.37319(9) 0.0283(6) Uani 1 d . . .
C23A C 0.12147(5) 1.5078(3) 0.41813(9) 0.0267(6) Uani 1 d . . .
C24A C 0.09415(5) 1.5269(4) 0.42317(9) 0.0288(6) Uani 1 d . . .
C25A C 0.08699(6) 1.5584(4) 0.46127(10) 0.0337(7) Uani 1 d . . .
H25A H 0.0678(6) 1.573(4) 0.4578(9) 0.040 Uiso 1 d . . R
C26A C 0.10300(7) 1.5745(4) 0.50284(10) 0.0398(8) Uani 1 d . . .
H26A H 0.0923(6) 1.601(4) 0.5239(10) 0.048 Uiso 1 d . . R
C27A C 0.13014(7) 1.5590(4) 0.51746(10) 0.0403(8) Uani 1 d . . .
H27A H 0.1383(6) 1.565(4) 0.5483(11) 0.048 Uiso 1 d . . R
C28A C 0.14870(6) 1.5216(4) 0.49464(10) 0.0348(7) Uani 1 d . . .
H28A H 0.1666(6) 1.511(4) 0.5106(10) 0.042 Uiso 1 d . . R
C29A C 0.14475(6) 1.4962(4) 0.45066(9) 0.0307(7) Uani 1 d . . .
H29A H 0.1609(6) 1.465(4) 0.4419(9) 0.037 Uiso 1 d . . R
C30A C 0.14085(5) 1.4661(4) 0.35230(9) 0.0281(6) Uani 1 d . . .
C31A C 0.13745(6) 1.3596(4) 0.31552(9) 0.0322(7) Uani 1 d . . .
H31A H 0.1211(6) 1.313(4) 0.3024(9) 0.039 Uiso 1 d . . R
C32A C 0.15821(6) 1.3301(4) 0.29752(10) 0.0356(7) Uani 1 d . . .
H32A H 0.1562(6) 1.260(4) 0.2744(10) 0.043 Uiso 1 d . . R
C33A C 0.16594(6) 1.5432(4) 0.36760(10) 0.0320(7) Uani 1 d . . .
H33A H 0.1687(6) 1.626(4) 0.3916(10) 0.038 Uiso 1 d . . R
C34A C 0.18575(6) 1.5024(4) 0.34811(10) 0.0351(7) Uani 1 d . . .
H34A H 0.2027(6) 1.545(4) 0.3594(10) 0.042 Uiso 1 d . . R
O3B O -0.14454(4) 1.3021(3) 0.31775(6) 0.0359(5) Uani 1 d . . .
O2B O -0.22684(4) 1.2901(3) 0.43348(7) 0.0491(6) Uani 1 d . . .
O1B O -0.24885(4) 1.4453(3) 0.37627(7) 0.0472(6) Uani 1 d . . .
H1B H -0.2636 1.4681 0.3837 0.071 Uiso 1 d . . R
O4B O -0.02941(5) 0.9835(4) 0.38609(10) 0.0740(9) Uani 1 d . . .
H4B H -0.0127 0.9895 0.4004 0.111 Uiso 1 d . . R
O5B O -0.02814(5) 1.1821(4) 0.43794(8) 0.0623(7) Uani 1 d . . .
C1B C -0.22808(6) 1.3593(4) 0.39883(9) 0.0334(7) Uani 1 d . . .
C2B C -0.20569(5) 1.3522(4) 0.37792(9) 0.0280(6) Uani 1 d . . .
C3B C -0.20727(6) 1.4293(4) 0.33786(9) 0.0312(7) Uani 1 d . . .
H3B H -0.2231(6) 1.490(4) 0.3235(9) 0.037 Uiso 1 d . . R
C4B C -0.18659(6) 1.4143(4) 0.31895(10) 0.0321(7) Uani 1 d . . .
H4BA H -0.1874(6) 1.458(4) 0.2919(10) 0.039 Uiso 1 d . . R
C5B C -0.16395(5) 1.3207(4) 0.33981(9) 0.0289(6) Uani 1 d . . .
C6B C -0.16210(6) 1.2427(4) 0.37962(9) 0.0307(7) Uani 1 d . . .
H6B H -0.1468(6) 1.172(4) 0.3926(9) 0.037 Uiso 1 d . . R
C7B C -0.18302(6) 1.2612(4) 0.39834(9) 0.0299(6) Uani 1 d . . .
H7B H -0.1824(6) 1.204(4) 0.4250(10) 0.036 Uiso 1 d . . R
C8B C -0.11898(5) 1.2532(4) 0.34059(9) 0.0308(7) Uani 1 d . . .
C9B C -0.10726(6) 1.1128(5) 0.32491(11) 0.0435(8) Uani 1 d . . .
H9B H -0.1177(7) 1.052(5) 0.3004(11) 0.052 Uiso 1 d . . R
C10B C -0.08144(6) 1.0649(5) 0.34565(12) 0.0482(9) Uani 1 d . . .
H10B H -0.0720(7) 0.951(5) 0.3339(11) 0.058 Uiso 1 d . . R
C11B C -0.06765(6) 1.1576(4) 0.38167(10) 0.0365(7) Uani 1 d . . .
C12B C -0.07968(6) 1.3019(4) 0.39656(10) 0.0372(7) Uani 1 d . . .
H12B H -0.0692(6) 1.375(4) 0.4213(10) 0.045 Uiso 1 d . . R
C13B C -0.10550(6) 1.3494(4) 0.37623(10) 0.0364(7) Uani 1 d . . .
H13B H -0.1137(6) 1.452(4) 0.3864(10) 0.044 Uiso 1 d . . R
C14B C -0.03983(6) 1.1075(5) 0.40468(11) 0.0442(8) Uani 1 d . . .
O3A O -0.17342(4) 1.8633(3) 0.21574(6) 0.0342(5) Uani 1 d . . .
O4A O -0.05893(4) 1.6007(3) 0.31494(7) 0.0521(6) Uani 1 d . . .
H4A H -0.0422 1.6045 0.3251 0.078 Uiso 1 d . . R
O5A O -0.04952(4) 1.7309(4) 0.25829(7) 0.0586(7) Uani 1 d . . .
O1A O -0.27579(4) 1.8115(3) 0.28290(7) 0.0429(5) Uani 1 d . . .
H1A H -0.2882 1.8430 0.2950 0.064 Uiso 1 d . . R
O2A O -0.25014(4) 1.9533(3) 0.33998(7) 0.0445(6) Uani 1 d . . .
C1A C -0.25308(6) 1.8805(4) 0.30538(9) 0.0311(7) Uani 1 d . . .
C2A C -0.23149(5) 1.8648(4) 0.28296(9) 0.0278(6) Uani 1 d . . .
C3A C -0.23601(6) 1.7887(4) 0.24229(9) 0.0299(6) Uani 1 d . . .
H3A H -0.2539(6) 1.734(4) 0.2301(9) 0.036 Uiso 1 d . . R
C4A C -0.21616(6) 1.7851(4) 0.22092(10) 0.0314(7) Uani 1 d . . .
H4AA H -0.2194(6) 1.732(4) 0.1915(10) 0.038 Uiso 1 d . . R
C5A C -0.19168(5) 1.8569(4) 0.24044(9) 0.0278(6) Uani 1 d . . .
C6A C -0.18681(6) 1.9338(4) 0.28096(9) 0.0327(7) Uani 1 d . . .
H6A H -0.1694(6) 1.982(4) 0.2950(10) 0.039 Uiso 1 d . . R
C7A C -0.20679(6) 1.9369(4) 0.30221(9) 0.0314(7) Uani 1 d . . .
H7A H -0.2038(6) 1.995(4) 0.3307(10) 0.038 Uiso 1 d . . R
C8A C -0.14750(5) 1.8128(4) 0.23295(9) 0.0270(6) Uani 1 d . . .
C9A C -0.12952(6) 1.8724(4) 0.21079(9) 0.0315(7) Uani 1 d . . .
H9A H -0.1366(6) 1.936(4) 0.1861(10) 0.038 Uiso 1 d . . R
C10A C -0.10316(6) 1.8273(4) 0.22530(10) 0.0337(7) Uani 1 d . . .
H10A H -0.0904(6) 1.864(4) 0.2104(10) 0.040 Uiso 1 d . . R
C11A C -0.09422(5) 1.7223(4) 0.26179(9) 0.0313(7) Uani 1 d . . .
C12A C -0.11254(6) 1.6590(4) 0.28302(10) 0.0336(7) Uani 1 d . . .
H12A H -0.1057(6) 1.587(4) 0.3101(10) 0.040 Uiso 1 d . . R
C13A C -0.13928(6) 1.7037(4) 0.26864(10) 0.0321(7) Uani 1 d . . .
H13A H -0.1515(6) 1.658(4) 0.2853(9) 0.039 Uiso 1 d . . R
C14A C -0.06552(6) 1.6843(4) 0.27812(10) 0.0371(7) Uani 1 d . . .
N2 N -0.04916(15) 2.1325(11) 0.1975(2) 0.138(2) Uiso 0.75 d . . D
C3 C -0.04180(14) 2.1548(10) 0.23298(19) 0.0922(14) Uiso 0.75 d . . D
C4 C -0.03357(13) 2.1740(10) 0.27878(18) 0.0922(14) Uiso 0.75 d . . D
H4C H -0.0290 2.0576 0.2916 0.138 Uiso 0.75 d . . R
H4D H -0.0478 2.2246 0.2890 0.138 Uiso 0.75 d . . R
H4E H -0.0184 2.2519 0.2865 0.138 Uiso 0.75 d . . R
N1 N 0.21131(7) 1.3889(5) 0.47294(13) 0.0806(11) Uani 1 d . . D
C1 C 0.22816(8) 1.3774(5) 0.45748(12) 0.0549(10) Uani 1 d . . D
C2 C 0.24985(8) 1.3633(6) 0.43796(12) 0.0695(12) Uani 1 d . . D
H2A H 0.2432 1.3644 0.4072 0.104 Uiso 1 d . . R
H2B H 0.2617 1.4630 0.4467 0.104 Uiso 1 d . . R
H2C H 0.2592 1.2525 0.4467 0.104 Uiso 1 d . . R
N3 N -0.0231(5) 1.627(4) 0.4928(6) 0.138(2) Uiso 0.25 d A 1 D
C5 C -0.0320(4) 1.659(3) 0.4581(6) 0.0922(14) Uiso 0.25 d A 1 D
C6 C -0.0567(4) 1.707(3) 0.4289(6) 0.0922(14) Uiso 0.25 d A 1 D
H6C H -0.0726 1.6465 0.4309 0.138 Uiso 0.25 d A 1 R
H6D H -0.0595 1.8349 0.4284 0.138 Uiso 0.25 d A 1 R
H6E H -0.0523 1.6707 0.4029 0.138 Uiso 0.25 d A 1 R
O2W O -0.03574(11) 1.4775(8) 0.48924(17) 0.0718(15) Uiso 0.50 d B 3 .
H2WA H -0.0319 1.3680 0.4848 0.108 Uiso 0.50 d B 3 R
H2WB H -0.0223 1.5430 0.4908 0.108 Uiso 0.50 d B 3 R
O1W O -0.0349(3) 1.635(2) 0.4734(4) 0.076(4) Uiso 0.25 d C 2 .
H1WA H -0.0471 1.5585 0.4711 0.114 Uiso 0.25 d C 2 R
H1WB H -0.0292 1.6767 0.4990 0.114 Uiso 0.25 d C 2 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
N1B C15B 1.334(5) . ?
N1B C19B 1.333(5) . ?
N2B C32B 1.345(4) . ?
N2B C34B 1.335(4) . ?
C15B H15B 0.97(4) . ?
C15B C16B 1.375(5) . ?
C16B H16B 0.96(3) . ?
C16B C17B 1.396(5) . ?
C17B C18B 1.395(5) . ?
C17B C20B 1.470(4) . ?
C18B H18B 0.97(3) . ?
C18B C19B 1.379(5) . ?
C19B H19B 1.06(4) . ?
C20B C21B 1.401(4) . ?
C20B C24B 1.408(4) . ?
C21B H21B 0.96(3) . ?
C21B C22B 1.394(4) . ?
C22B C23B 1.417(4) . ?
C22B C30B 1.467(4) . ?
C23B C24B 1.490(4) . ?
C23B C29B 1.386(4) . ?
C24B C25B 1.397(4) . ?
C25B H25B 0.98(3) . ?
C25B C26B 1.391(5) . ?
C26B H26B 1.03(3) . ?
C26B C27B 1.384(5) . ?
C27B H27B 0.97(4) . ?
C27B C28B 1.385(5) . ?
C28B H28B 0.94(3) . ?
C28B C29B 1.386(4) . ?
C29B H29B 1.00(3) . ?
C30B C31B 1.388(4) . ?
C30B C33B 1.390(4) . ?
C31B H31B 0.99(3) . ?
C31B C32B 1.373(4) . ?
C32B H32B 1.00(3) . ?
C33B H33B 0.94(3) . ?
C33B C34B 1.375(4) . ?
C34B H34B 0.99(3) . ?
N1A C15A 1.339(4) . ?
N1A C19A 1.337(4) . ?
N2A C32A 1.337(4) . ?
N2A C34A 1.334(4) . ?
C15A H15A 0.94(4) . ?
C15A C16A 1.377(4) . ?
C16A H16A 1.00(3) . ?
C16A C17A 1.394(4) . ?
C17A C18A 1.394(4) . ?
C17A C20A 1.481(4) . ?
C18A H18A 0.97(3) . ?
C18A C19A 1.376(4) . ?
C19A H19A 1.01(3) . ?
C20A C21A 1.401(4) . ?
C20A C24A 1.411(4) . ?
C21A H21A 1.01(3) . ?
C21A C22A 1.395(4) . ?
C22A C23A 1.425(4) . ?
C22A C30A 1.468(4) . ?
C23A C24A 1.484(4) . ?
C23A C29A 1.389(4) . ?
C24A C25A 1.389(4) . ?
C25A H25A 0.99(3) . ?
C25A C26A 1.389(4) . ?
C26A H26A 1.00(3) . ?
C26A C27A 1.379(5) . ?
C27A H27A 0.98(3) . ?
C27A C28A 1.386(4) . ?
C28A H28A 0.95(3) . ?
C28A C29A 1.389(4) . ?
C29A H29A 0.98(3) . ?
C30A C31A 1.395(4) . ?
C30A C33A 1.399(4) . ?
C31A H31A 0.92(3) . ?
C31A C32A 1.371(4) . ?
C32A H32A 0.89(3) . ?
C33A H33A 0.97(3) . ?
C33A C34A 1.374(4) . ?
C34A H34A 0.92(3) . ?
O3B C5B 1.385(3) . ?
O3B C8B 1.397(3) . ?
O2B C1B 1.214(3) . ?
O1B H1B 0.8818 . ?
O1B C1B 1.307(3) . ?
O4B H4B 0.8786 . ?
O4B C14B 1.291(4) . ?
O5B C14B 1.220(4) . ?
C1B C2B 1.492(4) . ?
C2B C3B 1.392(4) . ?
C2B C7B 1.375(4) . ?
C3B H3B 0.95(3) . ?
C3B C4B 1.373(4) . ?
C4B H4BA 0.92(3) . ?
C4B C5B 1.387(4) . ?
C5B C6B 1.386(4) . ?
C6B H6B 0.96(3) . ?
C6B C7B 1.383(4) . ?
C7B H7B 0.95(3) . ?
C8B C9B 1.368(4) . ?
C8B C13B 1.381(4) . ?
C9B H9B 0.95(3) . ?
C9B C10B 1.389(5) . ?
C10B H10B 1.10(4) . ?
C10B C11B 1.381(4) . ?
C11B C12B 1.387(4) . ?
C11B C14B 1.499(4) . ?
C12B H12B 1.00(3) . ?
C12B C13B 1.385(4) . ?
C13B H13B 0.97(3) . ?
O3A C5A 1.390(3) . ?
O3A C8A 1.377(3) . ?
O4A H4A 0.8533 . ?
O4A C14A 1.303(4) . ?
O5A C14A 1.224(4) . ?
O1A H1A 0.8693 . ?
O1A C1A 1.324(3) . ?
O2A C1A 1.211(3) . ?
C1A C2A 1.491(4) . ?
C2A C3A 1.388(4) . ?
C2A C7A 1.387(4) . ?
C3A H3A 1.00(3) . ?
C3A C4A 1.383(4) . ?
C4A H4AA 1.00(3) . ?
C4A C5A 1.379(4) . ?
C5A C6A 1.385(4) . ?
C6A H6A 0.97(3) . ?
C6A C7A 1.386(4) . ?
C7A H7A 0.99(3) . ?
C8A C9A 1.388(4) . ?
C8A C13A 1.380(4) . ?
C9A H9A 0.91(3) . ?
C9A C10A 1.377(4) . ?
C10A H10A 0.96(3) . ?
C10A C11A 1.386(4) . ?
C11A C12A 1.392(4) . ?
C11A C14A 1.483(4) . ?
C12A H12A 1.01(3) . ?
C12A C13A 1.394(4) . ?
C13A H13A 0.99(3) . ?
N2 C3 1.118(4) . ?
C3 C4 1.432(5) . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9602 . ?
C4 H4E 0.9596 . ?
N1 C1 1.120(4) . ?
C1 C2 1.433(5) . ?
C2 H2A 0.9599 . ?
C2 H2B 0.9598 . ?
C2 H2C 0.9601 . ?
N3 C5 1.119(4) . ?
N3 H2WB 0.6291 . ?
N3 H1WB 0.5576 . ?
C5 C6 1.432(5) . ?
C6 H6C 0.9599 . ?
C6 H6D 0.9600 . ?
C6 H6E 0.9604 . ?
O2W H2WA 0.8574 . ?
O2W H2WB 0.8463 . ?
O1W H1WA 0.8416 . ?
O1W H1WB 0.8602 . ?

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
C15B N1B C19B 118.5(3) . . ?
C34B N2B C32B 117.2(3) . . ?
N1B C15B H15B 121(2) . . ?
N1B C15B C16B 122.4(4) . . ?
C16B C15B H15B 117(2) . . ?
C15B C16B H16B 119(2) . . ?
C15B C16B C17B 120.3(4) . . ?
C17B C16B H16B 120(2) . . ?
C16B C17B C20B 119.4(3) . . ?
C18B C17B C16B 116.4(3) . . ?
C18B C17B C20B 124.1(3) . . ?
C17B C18B H18B 120(2) . . ?
C19B C18B C17B 120.0(4) . . ?
C19B C18B H18B 120(2) . . ?
N1B C19B C18B 122.5(4) . . ?
N1B C19B H19B 114(2) . . ?
C18B C19B H19B 123(2) . . ?
C21B C20B C17B 122.0(3) . . ?
C21B C20B C24B 107.9(3) . . ?
C24B C20B C17B 130.1(3) . . ?
C20B C21B H21B 124.9(18) . . ?
C22B C21B C20B 110.9(3) . . ?
C22B C21B H21B 124.2(18) . . ?
C21B C22B C23B 107.7(3) . . ?
C21B C22B C30B 123.7(3) . . ?
C23B C22B C30B 128.5(2) . . ?
C22B C23B C24B 106.6(2) . . ?
C29B C23B C22B 125.7(3) . . ?
C29B C23B C24B 127.3(3) . . ?
C20B C24B C23B 106.8(2) . . ?
C25B C24B C20B 127.0(3) . . ?
C25B C24B C23B 126.2(3) . . ?
C24B C25B H25B 115.2(19) . . ?
C26B C25B C24B 129.3(3) . . ?
C26B C25B H25B 115.5(19) . . ?
C25B C26B H26B 115.9(19) . . ?
C27B C26B C25B 129.2(3) . . ?
C27B C26B H26B 114.9(19) . . ?
C26B C27B H27B 115(2) . . ?
C26B C27B C28B 129.5(3) . . ?
C28B C27B H27B 116(2) . . ?
C27B C28B H28B 115(2) . . ?
C29B C28B C27B 128.4(3) . . ?
C29B C28B H28B 117(2) . . ?
C23B C29B C28B 129.9(3) . . ?
C23B C29B H29B 114.9(18) . . ?
C28B C29B H29B 115.3(18) . . ?
C31B C30B C22B 119.2(2) . . ?
C31B C30B C33B 117.1(3) . . ?
C33B C30B C22B 123.7(3) . . ?
C30B C31B H31B 119.6(18) . . ?
C32B C31B C30B 120.2(3) . . ?
C32B C31B H31B 120.2(18) . . ?
N2B C32B C31B 122.5(3) . . ?
N2B C32B H32B 116.0(18) . . ?
C31B C32B H32B 121.5(18) . . ?
C30B C33B H33B 119.0(19) . . ?
C34B C33B C30B 119.2(3) . . ?
C34B C33B H33B 121.9(19) . . ?
N2B C34B C33B 123.7(3) . . ?
N2B C34B H34B 113.0(18) . . ?
C33B C34B H34B 123.3(18) . . ?
C19A N1A C15A 117.2(3) . . ?
C34A N2A C32A 116.3(3) . . ?
N1A C15A H15A 115(2) . . ?
N1A C15A C16A 123.3(3) . . ?
C16A C15A H15A 121(2) . . ?
C15A C16A H16A 115.5(18) . . ?
C15A C16A C17A 119.7(3) . . ?
C17A C16A H16A 124.8(18) . . ?
C16A C17A C18A 116.7(3) . . ?
C16A C17A C20A 119.7(3) . . ?
C18A C17A C20A 123.6(3) . . ?
C17A C18A H18A 121.5(19) . . ?
C19A C18A C17A 120.0(3) . . ?
C19A C18A H18A 118.4(19) . . ?
N1A C19A C18A 123.1(3) . . ?
N1A C19A H19A 113.3(18) . . ?
C18A C19A H19A 123.5(19) . . ?
C21A C20A C17A 124.0(3) . . ?
C21A C20A C24A 107.8(2) . . ?
C24A C20A C17A 128.1(3) . . ?
C20A C21A H21A 124.9(17) . . ?
C22A C21A C20A 111.0(3) . . ?
C22A C21A H21A 124.0(17) . . ?
C21A C22A C23A 107.5(2) . . ?
C21A C22A C30A 125.5(2) . . ?
C23A C22A C30A 127.0(2) . . ?
C22A C23A C24A 106.6(2) . . ?
C29A C23A C22A 126.0(3) . . ?
C29A C23A C24A 127.2(3) . . ?
C20A C24A C23A 107.0(2) . . ?
C25A C24A C20A 126.3(3) . . ?
C25A C24A C23A 126.6(3) . . ?
C24A C25A H25A 114.5(18) . . ?
C26A C25A C24A 129.2(3) . . ?
C26A C25A H25A 116.3(18) . . ?
C25A C26A H26A 111.4(18) . . ?
C27A C26A C25A 129.3(3) . . ?
C27A C26A H26A 119.2(18) . . ?
C26A C27A H27A 119.0(19) . . ?
C26A C27A C28A 129.3(3) . . ?
C28A C27A H27A 111.5(19) . . ?
C27A C28A H28A 117.3(19) . . ?
C27A C28A C29A 128.7(3) . . ?
C29A C28A H28A 114.0(19) . . ?
C23A C29A H29A 116.7(17) . . ?
C28A C29A C23A 129.2(3) . . ?
C28A C29A H29A 114.1(17) . . ?
C31A C30A C22A 121.0(3) . . ?
C31A C30A C33A 115.7(3) . . ?
C33A C30A C22A 123.2(3) . . ?
C30A C31A H31A 120.4(19) . . ?
C32A C31A C30A 120.4(3) . . ?
C32A C31A H31A 119.2(19) . . ?
N2A C32A C31A 123.6(3) . . ?
N2A C32A H32A 116(2) . . ?
C31A C32A H32A 121(2) . . ?
C30A C33A H33A 118.3(18) . . ?
C34A C33A C30A 119.8(3) . . ?
C34A C33A H33A 121.9(18) . . ?
N2A C34A C33A 124.0(3) . . ?
N2A C34A H34A 116(2) . . ?
C33A C34A H34A 120(2) . . ?
C5B O3B C8B 118.9(2) . . ?
C1B O1B H1B 127.1 . . ?
C14B O4B H4B 101.6 . . ?
O2B C1B O1B 123.9(3) . . ?
O2B C1B C2B 122.3(3) . . ?
O1B C1B C2B 113.7(3) . . ?
C3B C2B C1B 122.3(3) . . ?
C7B C2B C1B 118.7(3) . . ?
C7B C2B C3B 118.9(3) . . ?
C2B C3B H3B 118.8(18) . . ?
C4B C3B C2B 120.6(3) . . ?
C4B C3B H3B 120.6(18) . . ?
C3B C4B H4BA 122.7(19) . . ?
C3B C4B C5B 119.8(3) . . ?
C5B C4B H4BA 117.5(19) . . ?
O3B C5B C4B 116.6(2) . . ?
O3B C5B C6B 123.0(2) . . ?
C6B C5B C4B 120.3(3) . . ?
C5B C6B H6B 118.9(18) . . ?
C7B C6B C5B 119.0(3) . . ?
C7B C6B H6B 122.0(18) . . ?
C2B C7B C6B 121.4(3) . . ?
C2B C7B H7B 118.5(18) . . ?
C6B C7B H7B 120.0(18) . . ?
C9B C8B O3B 117.5(3) . . ?
C9B C8B C13B 121.2(3) . . ?
C13B C8B O3B 121.2(3) . . ?
C8B C9B H9B 117(2) . . ?
C8B C9B C10B 119.3(3) . . ?
C10B C9B H9B 124(2) . . ?
C9B C10B H10B 120.1(18) . . ?
C11B C10B C9B 120.6(3) . . ?
C11B C10B H10B 119.3(18) . . ?
C10B C11B C12B 119.2(3) . . ?
C10B C11B C14B 121.5(3) . . ?
C12B C11B C14B 119.3(3) . . ?
C11B C12B H12B 119.1(18) . . ?
C13B C12B C11B 120.4(3) . . ?
C13B C12B H12B 120.4(18) . . ?
C8B C13B C12B 119.2(3) . . ?
C8B C13B H13B 120.6(19) . . ?
C12B C13B H13B 120.1(19) . . ?
O4B C14B C11B 114.7(3) . . ?
O5B C14B O4B 123.6(3) . . ?
O5B C14B C11B 121.6(3) . . ?
C8A O3A C5A 120.6(2) . . ?
C14A O4A H4A 109.7 . . ?
C1A O1A H1A 108.7 . . ?
O1A C1A C2A 112.9(2) . . ?
O2A C1A O1A 124.0(3) . . ?
O2A C1A C2A 123.1(3) . . ?
C3A C2A C1A 121.3(2) . . ?
C7A C2A C1A 119.1(2) . . ?
C7A C2A C3A 119.5(3) . . ?
C2A C3A H3A 116.6(17) . . ?
C4A C3A C2A 120.5(3) . . ?
C4A C3A H3A 122.8(17) . . ?
C3A C4A H4AA 120.7(17) . . ?
C5A C4A C3A 119.5(3) . . ?
C5A C4A H4AA 119.8(17) . . ?
C4A C5A O3A 116.4(2) . . ?
C4A C5A C6A 120.9(3) . . ?
C6A C5A O3A 122.4(2) . . ?
C5A C6A H6A 120.9(18) . . ?
C5A C6A C7A 119.4(3) . . ?
C7A C6A H6A 119.7(18) . . ?
C2A C7A H7A 119.4(17) . . ?
C6A C7A C2A 120.3(3) . . ?
C6A C7A H7A 120.2(17) . . ?
O3A C8A C9A 115.6(2) . . ?
O3A C8A C13A 124.0(2) . . ?
C13A C8A C9A 120.4(3) . . ?
C8A C9A H9A 115.8(19) . . ?
C10A C9A C8A 119.8(3) . . ?
C10A C9A H9A 124.3(19) . . ?
C9A C10A H10A 121.8(18) . . ?
C9A C10A C11A 121.0(3) . . ?
C11A C10A H10A 117.3(18) . . ?
C10A C11A C12A 118.7(3) . . ?
C10A C11A C14A 119.9(3) . . ?
C12A C11A C14A 121.5(3) . . ?
C11A C12A H12A 117.8(17) . . ?
C11A C12A C13A 120.9(3) . . ?
C13A C12A H12A 121.2(17) . . ?
C8A C13A C12A 119.2(3) . . ?
C8A C13A H13A 123.0(17) . . ?
C12A C13A H13A 117.8(17) . . ?
O4A C14A C11A 114.9(3) . . ?
O5A C14A O4A 123.5(3) . . ?
O5A C14A C11A 121.7(3) . . ?
N2 C3 C4 176.2(9) . . ?
C3 C4 H4C 109.2 . . ?
C3 C4 H4D 109.6 . . ?
C3 C4 H4E 109.7 . . ?
H4C C4 H4D 109.5 . . ?
H4C C4 H4E 109.5 . . ?
H4D C4 H4E 109.5 . . ?
N1 C1 C2 179.6(5) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.7 . . ?
C1 C2 H2C 109.4 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C5 N3 H2WB 97.3 . . ?
C5 N3 H1WA 58.3 . . ?
C5 N3 H1WB 94.9 . . ?
H2WB N3 H1WA 69.8 . . ?
H2WB N3 H1WB 138.8 . . ?
H1WA N3 H1WB 83.9 . . ?
N3 C5 C6 142(3) . . ?
N3 C5 H2WB 27.5 . . ?
N3 C5 H1WA 71.0 . . ?
N3 C5 H1WB 25.5 . . ?
C6 C5 H2WB 140.0 . . ?
C6 C5 H1WA 80.1 . . ?
C6 C5 H1WB 119.5 . . ?
H2WB C5 H1WA 59.9 . . ?
H2WB C5 H1WB 49.6 . . ?
H1WA C5 H1WB 68.5 . . ?
C5 C6 H6C 119.2 . . ?
C5 C6 H6D 111.3 . . ?
C5 C6 H6E 97.2 . . ?
H6C C6 H6D 109.4 . . ?
H6C C6 H6E 109.4 . . ?
H6D C6 H6E 109.5 . . ?
H2WA O2W H2WB 109.0 . . ?
H2WA O2W H1WA 130.1 . . ?
H2WB O2W H1WA 93.0 . . ?
H2WB O1W H1WA 88.0 . . ?
H2WB O1W H1WB 72.3 . . ?
H1WA O1W H1WB 113.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C33B H33B O2B 0.94(3) 2.59(3) 3.400(4) 144(2) 5_576
C34B H34B O2B 0.99(3) 2.70(3) 3.399(4) 128(2) 3_545
C15A H15A O5A 0.94(4) 2.52(4) 3.211(4) 131(3) .
C16A H16A O5A 1.00(3) 2.33(3) 3.245(4) 152(2) 2
C34A H34A O2A 0.92(3) 2.78(3) 3.444(4) 130(2) 3_545
O1B H1B N2B 0.88 1.77 2.602(3) 157.2 3_455
O4B H4B N1B 0.88 1.68 2.547(4) 167.2 .
O4A H4A N1A 0.85 1.77 2.609(3) 168.6 .
O1A H1A N2A 0.87 1.82 2.685(3) 172.1 3_455

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1B C15B C16B C17B 0.8(5) . . . . ?
C15B N1B C19B C18B 0.0(5) . . . . ?
C15B C16B C17B C18B 0.6(5) . . . . ?
C15B C16B C17B C20B 178.1(3) . . . . ?
C16B C17B C18B C19B -1.7(5) . . . . ?
C16B C17B C20B C21B -30.2(4) . . . . ?
C16B C17B C20B C24B 149.5(3) . . . . ?
C17B C18B C19B N1B 1.5(5) . . . . ?
C17B C20B C21B C22B -179.3(3) . . . . ?
C17B C20B C24B C23B -179.8(3) . . . . ?
C17B C20B C24B C25B -2.3(5) . . . . ?
C18B C17B C20B C21B 147.1(3) . . . . ?
C18B C17B C20B C24B -33.3(5) . . . . ?
C19B N1B C15B C16B -1.2(5) . . . . ?
C20B C17B C18B C19B -179.1(3) . . . . ?
C20B C21B C22B C23B -1.5(3) . . . . ?
C20B C21B C22B C30B -179.5(3) . . . . ?
C20B C24B C25B C26B -178.0(3) . . . . ?
C21B C20B C24B C23B -0.1(3) . . . . ?
C21B C20B C24B C25B 177.3(3) . . . . ?
C21B C22B C23B C24B 1.3(3) . . . . ?
C21B C22B C23B C29B -171.6(3) . . . . ?
C21B C22B C30B C31B 41.3(4) . . . . ?
C21B C22B C30B C33B -138.2(3) . . . . ?
C22B C23B C24B C20B -0.7(3) . . . . ?
C22B C23B C24B C25B -178.2(3) . . . . ?
C22B C23B C29B C28B 176.8(3) . . . . ?
C22B C30B C31B C32B 180.0(3) . . . . ?
C22B C30B C33B C34B -179.3(3) . . . . ?
C23B C22B C30B C31B -136.2(3) . . . . ?
C23B C22B C30B C33B 44.2(4) . . . . ?
C23B C24B C25B C26B -1.0(5) . . . . ?
C24B C20B C21B C22B 1.0(3) . . . . ?
C24B C23B C29B C28B 5.3(5) . . . . ?
C24B C25B C26B C27B 5.0(6) . . . . ?
C25B C26B C27B C28B -1.2(6) . . . . ?
C26B C27B C28B C29B -3.5(6) . . . . ?
C27B C28B C29B C23B 0.8(6) . . . . ?
C29B C23B C24B C20B 172.0(3) . . . . ?
C29B C23B C24B C25B -5.5(5) . . . . ?
C30B C22B C23B C24B 179.2(3) . . . . ?
C30B C22B C23B C29B 6.2(5) . . . . ?
C30B C31B C32B N2B -0.7(5) . . . . ?
C30B C33B C34B N2B -0.8(5) . . . . ?
C31B C30B C33B C34B 1.1(4) . . . . ?
C32B N2B C34B C33B -0.3(5) . . . . ?
C33B C30B C31B C32B -0.4(4) . . . . ?
C34B N2B C32B C31B 1.0(5) . . . . ?
N1A C15A C16A C17A 0.7(5) . . . . ?
C15A N1A C19A C18A -0.5(5) . . . . ?
C15A C16A C17A C18A -0.2(5) . . . . ?
C15A C16A C17A C20A 178.4(3) . . . . ?
C16A C17A C18A C19A -0.6(4) . . . . ?
C16A C17A C20A C21A -32.3(4) . . . . ?
C16A C17A C20A C24A 144.7(3) . . . . ?
C17A C18A C19A N1A 1.0(5) . . . . ?
C17A C20A C21A C22A 178.4(3) . . . . ?
C17A C20A C24A C23A -178.4(3) . . . . ?
C17A C20A C24A C25A -2.2(5) . . . . ?
C18A C17A C20A C21A 146.2(3) . . . . ?
C18A C17A C20A C24A -36.8(5) . . . . ?
C19A N1A C15A C16A -0.3(5) . . . . ?
C20A C17A C18A C19A -179.1(3) . . . . ?
C20A C21A C22A C23A -0.4(3) . . . . ?
C20A C21A C22A C30A 177.9(3) . . . . ?
C20A C24A C25A C26A -177.3(3) . . . . ?
C21A C20A C24A C23A -1.0(3) . . . . ?
C21A C20A C24A C25A 175.1(3) . . . . ?
C21A C22A C23A C24A -0.3(3) . . . . ?
C21A C22A C23A C29A 176.1(3) . . . . ?
C21A C22A C30A C31A -33.6(4) . . . . ?
C21A C22A C30A C33A 147.0(3) . . . . ?
C22A C23A C24A C20A 0.8(3) . . . . ?
C22A C23A C24A C25A -175.4(3) . . . . ?
C22A C23A C29A C28A 175.5(3) . . . . ?
C22A C30A C31A C32A -177.0(3) . . . . ?
C22A C30A C33A C34A 175.3(3) . . . . ?
C23A C22A C30A C31A 144.4(3) . . . . ?
C23A C22A C30A C33A -35.0(4) . . . . ?
C23A C24A C25A C26A -1.8(5) . . . . ?
C24A C20A C21A C22A 0.9(3) . . . . ?
C24A C23A C29A C28A -8.9(5) . . . . ?
C24A C25A C26A C27A -1.9(6) . . . . ?
C25A C26A C27A C28A -0.6(6) . . . . ?
C26A C27A C28A C29A 2.5(6) . . . . ?
C27A C28A C29A C23A 2.5(5) . . . . ?
C29A C23A C24A C20A -175.5(3) . . . . ?
C29A C23A C24A C25A 8.3(5) . . . . ?
C30A C22A C23A C24A -178.5(3) . . . . ?
C30A C22A C23A C29A -2.1(5) . . . . ?
C30A C31A C32A N2A 1.4(5) . . . . ?
C30A C33A C34A N2A 2.2(5) . . . . ?
C31A C30A C33A C34A -4.1(4) . . . . ?
C32A N2A C34A C33A 1.6(4) . . . . ?
C33A C30A C31A C32A 2.4(4) . . . . ?
C34A N2A C32A C31A -3.4(4) . . . . ?
O3B C5B C6B C7B -176.9(3) . . . . ?
O3B C8B C9B C10B 177.3(3) . . . . ?
O3B C8B C13B C12B -176.6(3) . . . . ?
O2B C1B C2B C3B 179.0(3) . . . . ?
O2B C1B C2B C7B 1.1(4) . . . . ?
O1B C1B C2B C3B -0.6(4) . . . . ?
O1B C1B C2B C7B -178.5(3) . . . . ?
C1B C2B C3B C4B -177.6(3) . . . . ?
C1B C2B C7B C6B 176.9(3) . . . . ?
C2B C3B C4B C5B 0.3(4) . . . . ?
C3B C2B C7B C6B -1.0(4) . . . . ?
C3B C4B C5B O3B 176.4(3) . . . . ?
C3B C4B C5B C6B -0.1(4) . . . . ?
C4B C5B C6B C7B -0.6(4) . . . . ?
C5B O3B C8B C9B 129.8(3) . . . . ?
C5B O3B C8B C13B -53.8(4) . . . . ?
C5B C6B C7B C2B 1.2(4) . . . . ?
C7B C2B C3B C4B 0.3(4) . . . . ?
C8B O3B C5B C4B 163.2(3) . . . . ?
C8B O3B C5B C6B -20.3(4) . . . . ?
C8B C9B C10B C11B -0.1(5) . . . . ?
C9B C8B C13B C12B -0.4(5) . . . . ?
C9B C10B C11B C12B -1.2(5) . . . . ?
C9B C10B C11B C14B 179.7(3) . . . . ?
C10B C11B C12B C13B 1.8(5) . . . . ?
C10B C11B C14B O4B 5.6(5) . . . . ?
C10B C11B C14B O5B -175.6(4) . . . . ?
C11B C12B C13B C8B -1.0(5) . . . . ?
C12B C11B C14B O4B -173.4(3) . . . . ?
C12B C11B C14B O5B 5.3(5) . . . . ?
C13B C8B C9B C10B 0.9(5) . . . . ?
C14B C11B C12B C13B -179.1(3) . . . . ?
O3A C5A C6A C7A 174.2(3) . . . . ?
O3A C8A C9A C10A -179.4(3) . . . . ?
O3A C8A C13A C12A 179.2(3) . . . . ?
O1A C1A C2A C3A 1.5(4) . . . . ?
O1A C1A C2A C7A 177.9(3) . . . . ?
O2A C1A C2A C3A -176.6(3) . . . . ?
O2A C1A C2A C7A -0.2(4) . . . . ?
C1A C2A C3A C4A 176.1(3) . . . . ?
C1A C2A C7A C6A -176.2(3) . . . . ?
C2A C3A C4A C5A 0.4(4) . . . . ?
C3A C2A C7A C6A 0.3(4) . . . . ?
C3A C4A C5A O3A -174.5(2) . . . . ?
C3A C4A C5A C6A -0.5(4) . . . . ?
C4A C5A C6A C7A 0.6(4) . . . . ?
C5A O3A C8A C9A -161.9(2) . . . . ?
C5A O3A C8A C13A 21.0(4) . . . . ?
C5A C6A C7A C2A -0.4(4) . . . . ?
C7A C2A C3A C4A -0.3(4) . . . . ?
C8A O3A C5A C4A -135.8(3) . . . . ?
C8A O3A C5A C6A 50.3(4) . . . . ?
C8A C9A C10A C11A 0.3(4) . . . . ?
C9A C8A C13A C12A 2.2(4) . . . . ?
C9A C10A C11A C12A 1.6(4) . . . . ?
C9A C10A C11A C14A -176.6(3) . . . . ?
C10A C11A C12A C13A -1.6(4) . . . . ?
C10A C11A C14A O4A 173.1(3) . . . . ?
C10A C11A C14A O5A -6.0(5) . . . . ?
C11A C12A C13A C8A -0.3(4) . . . . ?
C12A C11A C14A O4A -5.0(4) . . . . ?
C12A C11A C14A O5A 175.8(3) . . . . ?
C13A C8A C9A C10A -2.2(4) . . . . ?
C14A C11A C12A C13A 176.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
