# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_gopi
_database_code_depnum_ccdc_archive 'CCDC 1535512'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'C19 H13 N O3'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N O3'
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.350(4)
_cell_length_b                   8.514(3)
_cell_length_c                   18.643(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.789(18)
_cell_angle_gamma                90.00
_cell_volume                     1441.3(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2012
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      29.10

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12578
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_sigmaI/netI    0.1097
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2506
_reflns_number_gt                1318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_data_reduction        'Bruker SAINT, SADABS and XPREP'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0638P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2506
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3601(2) 0.0893(2) 0.53637(11) 0.0250(5) Uani 1 1 d . . .
N1 N 0.6575(3) 0.1894(3) 0.81713(15) 0.0323(7) Uani 1 1 d . . .
C1 C 0.4145(3) 0.2131(3) 0.56349(16) 0.0209(7) Uani 1 1 d . . .
O2 O 1.1429(2) 0.3488(2) 0.76218(11) 0.0281(6) Uani 1 1 d . . .
C2 C 0.3582(3) 0.3734(3) 0.54846(15) 0.0186(7) Uani 1 1 d . . .
O3 O 1.2761(2) 0.2255(2) 0.68916(11) 0.0254(5) Uani 1 1 d . . .
C3 C 0.2270(3) 0.4234(4) 0.50094(16) 0.0235(7) Uani 1 1 d . . .
H3 H 0.1609 0.3504 0.4719 0.028 Uiso 1 1 calc R . .
C4 C 0.1969(4) 0.5811(4) 0.49754(17) 0.0282(8) Uani 1 1 d . . .
H4 H 0.1080 0.6183 0.4660 0.034 Uiso 1 1 calc R . .
C5 C 0.2958(4) 0.6884(4) 0.54012(16) 0.0274(8) Uani 1 1 d . . .
H5 H 0.2732 0.7974 0.5366 0.033 Uiso 1 1 calc R . .
C6 C 0.4263(3) 0.6383(4) 0.58726(16) 0.0236(7) Uani 1 1 d . . .
H6 H 0.4934 0.7116 0.6155 0.028 Uiso 1 1 calc R . .
C7 C 0.4558(3) 0.4793(3) 0.59188(15) 0.0202(7) Uani 1 1 d . . .
C8 C 0.5880(3) 0.3960(3) 0.64043(16) 0.0210(7) Uani 1 1 d . . .
H8A H 0.6806 0.4285 0.6277 0.025 Uiso 1 1 calc R . .
H8B H 0.5956 0.4178 0.6934 0.025 Uiso 1 1 calc R . .
C9 C 0.5553(3) 0.2239(3) 0.62278(16) 0.0177(7) Uani 1 1 d . . .
C10 C 0.5740(3) 0.0977(3) 0.68240(16) 0.0216(7) Uani 1 1 d . . .
H10 H 0.4953 0.0156 0.6735 0.026 Uiso 1 1 calc R . .
C11 C 0.6234(3) 0.1467(3) 0.75769(18) 0.0230(7) Uani 1 1 d . . .
C12 C 0.6714(3) 0.0962(3) 0.62805(16) 0.0210(7) Uani 1 1 d . . .
H12 H 0.6414 0.0138 0.5891 0.025 Uiso 1 1 calc R . .
C13 C 0.8319(3) 0.1288(3) 0.64520(16) 0.0180(7) Uani 1 1 d . . .
C14 C 0.9024(3) 0.2331(3) 0.70123(15) 0.0193(7) Uani 1 1 d . . .
H14 H 0.8495 0.2844 0.7321 0.023 Uiso 1 1 calc R . .
C15 C 1.0493(3) 0.2575(3) 0.70929(16) 0.0192(7) Uani 1 1 d . . .
C16 C 1.2775(3) 0.3563(4) 0.73766(19) 0.0339(9) Uani 1 1 d . . .
H16A H 1.2830 0.4562 0.7113 0.041 Uiso 1 1 calc R . .
H16B H 1.3637 0.3498 0.7804 0.041 Uiso 1 1 calc R . .
C17 C 1.1286(3) 0.1846(3) 0.66513(16) 0.0195(7) Uani 1 1 d . . .
C18 C 1.0647(3) 0.0821(3) 0.61064(15) 0.0185(7) Uani 1 1 d . . .
H18 H 1.1194 0.0320 0.5803 0.022 Uiso 1 1 calc R . .
C19 C 0.9142(3) 0.0549(3) 0.60209(16) 0.0194(7) Uani 1 1 d . . .
H19 H 0.8661 -0.0170 0.5652 0.023 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(3) . ?
N1 C11 1.137(4) . ?
C1 C2 1.465(4) . ?
C1 C9 1.507(4) . ?
O2 C15 1.390(3) . ?
O2 C16 1.440(3) . ?
C2 C7 1.396(4) . ?
C2 C3 1.397(4) . ?
O3 C17 1.389(3) . ?
O3 C16 1.432(3) . ?
C3 C4 1.370(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.522(4) . ?
C8 C9 1.517(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C12 1.523(4) . ?
C9 C10 1.526(4) . ?
C10 C11 1.431(4) . ?
C10 C12 1.515(4) . ?
C10 H10 1.0000 . ?
C12 C13 1.484(4) . ?
C12 H12 1.0000 . ?
C13 C19 1.388(4) . ?
C13 C14 1.409(4) . ?
C14 C15 1.362(4) . ?
C14 H14 0.9500 . ?
C15 C17 1.380(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.365(4) . ?
C18 C19 1.398(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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 128.8(3) . . ?
O1 C1 C9 124.0(3) . . ?
C2 C1 C9 107.1(2) . . ?
C15 O2 C16 104.4(2) . . ?
C7 C2 C3 121.6(3) . . ?
C7 C2 C1 109.6(3) . . ?
C3 C2 C1 128.8(3) . . ?
C17 O3 C16 104.9(2) . . ?
C4 C3 C2 117.9(3) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 118.2(3) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 120.3(3) . . ?
C6 C7 C8 128.0(3) . . ?
C2 C7 C8 111.7(3) . . ?
C9 C8 C7 103.2(2) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
C1 C9 C8 108.3(2) . . ?
C1 C9 C12 119.3(2) . . ?
C8 C9 C12 124.9(2) . . ?
C1 C9 C10 114.8(2) . . ?
C8 C9 C10 122.7(2) . . ?
C12 C9 C10 59.61(17) . . ?
C11 C10 C12 123.6(3) . . ?
C11 C10 C9 117.6(3) . . ?
C12 C10 C9 60.12(18) . . ?
C11 C10 H10 114.8 . . ?
C12 C10 H10 114.8 . . ?
C9 C10 H10 114.8 . . ?
N1 C11 C10 177.2(3) . . ?
C13 C12 C10 126.3(3) . . ?
C13 C12 C9 123.3(2) . . ?
C10 C12 C9 60.28(18) . . ?
C13 C12 H12 112.4 . . ?
C10 C12 H12 112.4 . . ?
C9 C12 H12 112.4 . . ?
C19 C13 C14 119.3(3) . . ?
C19 C13 C12 117.5(3) . . ?
C14 C13 C12 123.2(2) . . ?
C15 C14 C13 117.3(2) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C17 122.5(3) . . ?
C14 C15 O2 127.7(2) . . ?
C17 C15 O2 109.8(3) . . ?
O3 C16 O2 106.8(2) . . ?
O3 C16 H16A 110.4 . . ?
O2 C16 H16A 110.4 . . ?
O3 C16 H16B 110.4 . . ?
O2 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C18 C17 C15 122.0(3) . . ?
C18 C17 O3 128.7(3) . . ?
C15 C17 O3 109.2(2) . . ?
C17 C18 C19 116.2(3) . . ?
C17 C18 H18 121.9 . . ?
C19 C18 H18 121.9 . . ?
C13 C19 C18 122.8(3) . . ?
C13 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?

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
O1 C1 C2 C7 180.0(3) . . . . ?
C9 C1 C2 C7 1.9(3) . . . . ?
O1 C1 C2 C3 1.8(5) . . . . ?
C9 C1 C2 C3 -176.2(3) . . . . ?
C7 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C2 1.8(4) . . . . ?
C5 C6 C7 C8 -178.4(3) . . . . ?
C3 C2 C7 C6 -1.8(4) . . . . ?
C1 C2 C7 C6 179.9(2) . . . . ?
C3 C2 C7 C8 178.4(2) . . . . ?
C1 C2 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C9 178.2(3) . . . . ?
C2 C7 C8 C9 -1.9(3) . . . . ?
O1 C1 C9 C8 178.7(3) . . . . ?
C2 C1 C9 C8 -3.2(3) . . . . ?
O1 C1 C9 C12 27.6(4) . . . . ?
C2 C1 C9 C12 -154.3(2) . . . . ?
O1 C1 C9 C10 -40.1(4) . . . . ?
C2 C1 C9 C10 138.0(2) . . . . ?
C7 C8 C9 C1 3.0(3) . . . . ?
C7 C8 C9 C12 152.1(3) . . . . ?
C7 C8 C9 C10 -134.5(3) . . . . ?
C1 C9 C10 C11 -134.5(3) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C12 C9 C10 C11 114.8(3) . . . . ?
C1 C9 C10 C12 110.7(3) . . . . ?
C8 C9 C10 C12 -114.3(3) . . . . ?
C12 C10 C11 N1 133(7) . . . . ?
C9 C10 C11 N1 62(7) . . . . ?
C11 C10 C12 C13 6.3(5) . . . . ?
C9 C10 C12 C13 111.4(3) . . . . ?
C11 C10 C12 C9 -105.1(3) . . . . ?
C1 C9 C12 C13 140.6(3) . . . . ?
C8 C9 C12 C13 -5.4(4) . . . . ?
C10 C9 C12 C13 -116.2(3) . . . . ?
C1 C9 C12 C10 -103.3(3) . . . . ?
C8 C9 C12 C10 110.7(3) . . . . ?
C10 C12 C13 C19 150.5(3) . . . . ?
C9 C12 C13 C19 -134.2(3) . . . . ?
C10 C12 C13 C14 -31.3(4) . . . . ?
C9 C12 C13 C14 44.0(4) . . . . ?
C19 C13 C14 C15 0.9(4) . . . . ?
C12 C13 C14 C15 -177.4(3) . . . . ?
C13 C14 C15 C17 0.1(4) . . . . ?
C13 C14 C15 O2 -176.9(3) . . . . ?
C16 O2 C15 C14 -170.0(3) . . . . ?
C16 O2 C15 C17 12.7(3) . . . . ?
C17 O3 C16 O2 21.7(3) . . . . ?
C15 O2 C16 O3 -21.1(3) . . . . ?
C14 C15 C17 C18 -0.5(5) . . . . ?
O2 C15 C17 C18 177.0(3) . . . . ?
C14 C15 C17 O3 -176.6(2) . . . . ?
O2 C15 C17 O3 0.8(3) . . . . ?
C16 O3 C17 C18 170.1(3) . . . . ?
C16 O3 C17 C15 -14.1(3) . . . . ?
C15 C17 C18 C19 0.0(4) . . . . ?
O3 C17 C18 C19 175.3(3) . . . . ?
C14 C13 C19 C18 -1.4(4) . . . . ?
C12 C13 C19 C18 176.9(3) . . . . ?
C17 C18 C19 C13 1.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_inn
_database_code_depnum_ccdc_archive 'CCDC 1535511'
_audit_update_record             
;
2017-03-01 deposited with the CCDC.
2017-04-04 downloaded from the CCDC.
;

_audit_creation_method           'Manual edit of SHELXL-97 CIF'
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   7.199(3)
_cell_length_b                   13.738(5)
_cell_length_c                   30.836(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3050(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3907
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25.3

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   numbus

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23094
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.34
_reflns_number_total             5564
_reflns_number_gt                4866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0754P)²+0.1625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?


_refine_ls_number_reflns         5564
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1276
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.1885(3) -0.23597(14) 0.03090(6) 0.0277(5) Uani 1 1 d . . .
H1 H -0.1840 -0.2874 0.0150 0.033 Uiso 1 1 calc R . .
O2 O -0.2287(2) 0.33304(11) 0.04474(5) 0.0299(4) Uani 1 1 d . . .
C4 C -0.1892(4) -0.23394(18) 0.07509(7) 0.0242(5) Uani 1 1 d . . .
C6 C -0.1964(3) -0.13819(17) 0.08867(7) 0.0233(5) Uani 1 1 d . . .
C10 C -0.2039(3) -0.07837(17) 0.05104(7) 0.0233(5) Uani 1 1 d . . .
C11 C -0.1926(4) -0.11352(18) 0.13594(7) 0.0259(5) Uani 1 1 d . . .
H11A H -0.2736 -0.0583 0.1412 0.031 Uiso 1 1 calc R . .
H11B H -0.0675 -0.0947 0.1440 0.031 Uiso 1 1 calc R . .
C12 C -0.2151(3) 0.02886(16) 0.04890(7) 0.0236(5) Uani 1 1 d . . .
N18 N -0.1794(3) -0.11156(15) -0.06633(7) 0.0342(5) Uani 1 1 d . . .
C19 C -0.2161(4) -0.38009(19) 0.17580(8) 0.0307(6) Uani 1 1 d . . .
H19 H -0.2378 -0.3700 0.2052 0.037 Uiso 1 1 calc R . .
C21 C -0.1310(3) 0.18824(18) 0.07706(8) 0.0266(6) Uani 1 1 d . . .
H21 H -0.0689 0.2259 0.0975 0.032 Uiso 1 1 calc R . .
C22 C -0.3195(4) 0.07569(18) 0.01698(8) 0.0262(6) Uani 1 1 d . . .
H22 H -0.3857 0.0385 -0.0029 0.031 Uiso 1 1 calc R . .
C23 C -0.2322(4) 0.23254(17) 0.04446(8) 0.0247(5) Uani 1 1 d . . .
C24 C -0.1964(4) -0.14138(18) 0.01590(8) 0.0264(5) Uani 1 1 d . . .
C28 C -0.1877(3) -0.12297(17) -0.02917(8) 0.0271(6) Uani 1 1 d . . .
C31 C -0.3270(3) 0.17681(17) 0.01417(8) 0.0249(5) Uani 1 1 d . . .
H31 H -0.3949 0.2066 -0.0078 0.030 Uiso 1 1 calc R . .
C32 C -0.1842(4) -0.31860(18) 0.10353(8) 0.0260(6) Uani 1 1 d . . .
C33 C -0.2130(3) -0.30102(18) 0.14789(7) 0.0254(6) Uani 1 1 d . . .
C34 C -0.1224(4) 0.08728(18) 0.07922(8) 0.0265(6) Uani 1 1 d . . .
H34 H -0.0538 0.0580 0.1012 0.032 Uiso 1 1 calc R . .
C36 C -0.3231(4) 0.38225(18) 0.01031(8) 0.0331(6) Uani 1 1 d . . .
H36A H -0.2736 0.3612 -0.0170 0.050 Uiso 1 1 calc R . .
H36B H -0.3059 0.4512 0.0133 0.050 Uiso 1 1 calc R . .
H36C H -0.4533 0.3673 0.0116 0.050 Uiso 1 1 calc R . .
C39 C -0.1531(4) -0.41318(19) 0.08870(8) 0.0304(6) Uani 1 1 d . . .
H39 H -0.1302 -0.4241 0.0594 0.036 Uiso 1 1 calc R . .
C40 C -0.2550(4) -0.19922(17) 0.16443(8) 0.0290(6) Uani 1 1 d . . .
H40A H -0.1970 -0.1920 0.1926 0.035 Uiso 1 1 calc R . .
H40B H -0.3881 -0.1940 0.1687 0.035 Uiso 1 1 calc R . .
C41 C -0.1877(4) -0.47353(19) 0.16081(8) 0.0346(6) Uani 1 1 d . . .
H41 H -0.1899 -0.5254 0.1802 0.042 Uiso 1 1 calc R . .
C45 C -0.1561(4) -0.49057(19) 0.11726(8) 0.0336(6) Uani 1 1 d . . .
H45 H -0.1370 -0.5537 0.1073 0.040 Uiso 1 1 calc R . .
O3 O 0.2490(3) 0.32832(13) 0.14541(5) 0.0378(5) Uani 1 1 d . . .
N5 N 0.2851(3) -0.23993(14) 0.13482(6) 0.0267(5) Uani 1 1 d . . .
H5 H 0.2876 -0.2915 0.1191 0.032 Uiso 1 1 calc R . .
C7 C 0.2668(4) 0.22904(17) 0.14644(7) 0.0268(6) Uani 1 1 d . . .
N8 N 0.3026(3) -0.11411(15) 0.03751(7) 0.0320(5) Uani 1 1 d . . .
C9 C 0.2922(4) -0.14500(17) 0.11976(7) 0.0263(6) Uani 1 1 d . . .
C13 C 0.2978(4) -0.12660(17) 0.07427(8) 0.0267(5) Uani 1 1 d . . .
C14 C 0.1688(4) 0.18152(18) 0.17860(8) 0.0289(6) Uani 1 1 d . . .
H14 H 0.0982 0.2173 0.1982 0.035 Uiso 1 1 calc R . .
C15 C 0.2734(4) -0.23747(18) 0.17868(8) 0.0247(5) Uani 1 1 d . . .
C16 C 0.3737(3) 0.17599(18) 0.11733(8) 0.0271(6) Uani 1 1 d . . .
H16 H 0.4408 0.2076 0.0957 0.033 Uiso 1 1 calc R . .
C17 C 0.2790(3) -0.32072(18) 0.20750(7) 0.0250(5) Uani 1 1 d . . .
C20 C 0.2808(3) 0.02574(17) 0.15256(7) 0.0243(5) Uani 1 1 d . . .
C25 C 0.2826(3) -0.08124(18) 0.15506(7) 0.0246(5) Uani 1 1 d . . .
C26 C 0.3194(3) -0.30172(18) 0.25133(8) 0.0261(5) Uani 1 1 d . . .
C27 C 0.3322(4) -0.37975(19) 0.27978(8) 0.0306(6) Uani 1 1 d . . .
H27 H 0.3569 -0.3682 0.3089 0.037 Uiso 1 1 calc R . .
C29 C 0.2706(3) -0.14153(17) 0.19208(7) 0.0256(5) Uani 1 1 d . . .
C30 C 0.3796(3) 0.07485(18) 0.12084(8) 0.0255(5) Uani 1 1 d . . .
H30 H 0.4516 0.0395 0.1014 0.031 Uiso 1 1 calc R . .
C35 C 0.1748(4) 0.08072(18) 0.18196(7) 0.0266(6) Uani 1 1 d . . .
H35 H 0.1084 0.0495 0.2038 0.032 Uiso 1 1 calc R . .
C37 C 0.3085(4) -0.47493(19) 0.26535(8) 0.0331(6) Uani 1 1 d . . .
H37 H 0.3204 -0.5264 0.2847 0.040 Uiso 1 1 calc R . .
C38 C 0.2527(4) -0.41677(18) 0.19355(8) 0.0289(6) Uani 1 1 d . . .
H38 H 0.2250 -0.4290 0.1646 0.035 Uiso 1 1 calc R . .
C42 C 0.3644(4) -0.19852(17) 0.26539(8) 0.0295(6) Uani 1 1 d . . .
H42A H 0.4968 -0.1878 0.2620 0.035 Uiso 1 1 calc R . .
H42B H 0.3351 -0.1918 0.2959 0.035 Uiso 1 1 calc R . .
C44 C 0.2674(4) -0.49341(19) 0.22218(8) 0.0336(6) Uani 1 1 d . . .
H44 H 0.2498 -0.5570 0.2126 0.040 Uiso 1 1 calc R . .
C46 C 0.2599(4) -0.11969(17) 0.24005(7) 0.0270(6) Uani 1 1 d . . .
H46A H 0.1310 -0.1180 0.2492 0.032 Uiso 1 1 calc R . .
H46B H 0.3146 -0.0565 0.2459 0.032 Uiso 1 1 calc R . .
C51 C 0.3451(5) 0.3793(2) 0.11150(9) 0.0480(8) Uani 1 1 d . . .
H51A H 0.4763 0.3684 0.1142 0.072 Uiso 1 1 calc R . .
H51B H 0.3197 0.4477 0.1137 0.072 Uiso 1 1 calc R . .
H51C H 0.3034 0.3559 0.0838 0.072 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.363(3) . ?
N1 C24 1.380(3) . ?
N1 H1 0.8600 . ?
O2 C23 1.381(3) . ?
O2 C36 1.430(3) . ?
C4 C6 1.382(3) . ?
C4 C32 1.457(3) . ?
C6 C10 1.423(3) . ?
C6 C11 1.497(3) . ?
C10 C24 1.388(3) . ?
C10 C12 1.477(3) . ?
C11 C40 1.536(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C22 1.396(3) . ?
C12 C34 1.401(3) . ?
N18 C28 1.158(3) . ?
C19 C41 1.380(4) . ?
C19 C33 1.386(3) . ?
C19 H19 0.9300 . ?
C21 C23 1.382(3) . ?
C21 C34 1.390(3) . ?
C21 H21 0.9300 . ?
C22 C31 1.393(3) . ?
C22 H22 0.9300 . ?
C23 C31 1.387(3) . ?
C24 C28 1.414(4) . ?
C31 H31 0.9300 . ?
C32 C39 1.396(3) . ?
C32 C33 1.404(3) . ?
C33 C40 1.519(3) . ?
C34 H34 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C39 C45 1.381(3) . ?
C39 H39 0.9300 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 C45 1.382(4) . ?
C41 H41 0.9300 . ?
C45 H45 0.9300 . ?
O3 C7 1.370(3) . ?
O3 C51 1.436(3) . ?
N5 C15 1.356(3) . ?
N5 C9 1.385(3) . ?
N5 H5 0.8600 . ?
C7 C14 1.381(3) . ?
C7 C16 1.389(3) . ?
N8 C13 1.147(3) . ?
C9 C25 1.399(3) . ?
C9 C13 1.426(3) . ?
C14 C35 1.389(3) . ?
C14 H14 0.9300 . ?
C15 C29 1.381(3) . ?
C15 C17 1.449(3) . ?
C16 C30 1.394(3) . ?
C16 H16 0.9300 . ?
C17 C38 1.401(3) . ?
C17 C26 1.407(3) . ?
C20 C30 1.385(3) . ?
C20 C35 1.405(3) . ?
C20 C25 1.472(3) . ?
C25 C29 1.413(3) . ?
C26 C27 1.388(3) . ?
C26 C42 1.517(3) . ?
C27 C37 1.392(4) . ?
C27 H27 0.9300 . ?
C29 C46 1.511(3) . ?
C30 H30 0.9300 . ?
C35 H35 0.9300 . ?
C37 C44 1.387(4) . ?
C37 H37 0.9300 . ?
C38 C44 1.378(3) . ?
C38 H38 0.9300 . ?
C42 C46 1.533(3) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C44 H44 0.9300 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C24 108.4(2) . . ?
C4 N1 H1 125.8 . . ?
C24 N1 H1 125.8 . . ?
C23 O2 C36 117.33(18) . . ?
N1 C4 C6 108.8(2) . . ?
N1 C4 C32 125.8(2) . . ?
C6 C4 C32 125.3(2) . . ?
C4 C6 C10 107.7(2) . . ?
C4 C6 C11 120.7(2) . . ?
C10 C6 C11 131.6(2) . . ?
C24 C10 C6 106.0(2) . . ?
C24 C10 C12 126.1(2) . . ?
C6 C10 C12 127.9(2) . . ?
C6 C11 C40 112.2(2) . . ?
C6 C11 H11A 109.2 . . ?
C40 C11 H11A 109.2 . . ?
C6 C11 H11B 109.2 . . ?
C40 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C22 C12 C34 117.6(2) . . ?
C22 C12 C10 121.4(2) . . ?
C34 C12 C10 121.0(2) . . ?
C41 C19 C33 121.3(2) . . ?
C41 C19 H19 119.4 . . ?
C33 C19 H19 119.4 . . ?
C23 C21 C34 119.9(2) . . ?
C23 C21 H21 120.1 . . ?
C34 C21 H21 120.1 . . ?
C31 C22 C12 121.6(2) . . ?
C31 C22 H22 119.2 . . ?
C12 C22 H22 119.2 . . ?
O2 C23 C21 115.2(2) . . ?
O2 C23 C31 124.4(2) . . ?
C21 C23 C31 120.4(2) . . ?
N1 C24 C10 109.1(2) . . ?
N1 C24 C28 119.7(2) . . ?
C10 C24 C28 131.1(2) . . ?
N18 C28 C24 177.4(3) . . ?
C23 C31 C22 119.3(2) . . ?
C23 C31 H31 120.4 . . ?
C22 C31 H31 120.4 . . ?
C39 C32 C33 120.2(2) . . ?
C39 C32 C4 123.4(2) . . ?
C33 C32 C4 116.4(2) . . ?
C19 C33 C32 118.2(2) . . ?
C19 C33 C40 120.6(2) . . ?
C32 C33 C40 121.0(2) . . ?
C21 C34 C12 121.2(2) . . ?
C21 C34 H34 119.4 . . ?
C12 C34 H34 119.4 . . ?
O2 C36 H36A 109.5 . . ?
O2 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O2 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C45 C39 C32 120.4(2) . . ?
C45 C39 H39 119.8 . . ?
C32 C39 H39 119.8 . . ?
C33 C40 C11 117.1(2) . . ?
C33 C40 H40A 108.0 . . ?
C11 C40 H40A 108.0 . . ?
C33 C40 H40B 108.0 . . ?
C11 C40 H40B 108.0 . . ?
H40A C40 H40B 107.3 . . ?
C19 C41 C45 120.5(2) . . ?
C19 C41 H41 119.8 . . ?
C45 C41 H41 119.8 . . ?
C39 C45 C41 119.5(2) . . ?
C39 C45 H45 120.3 . . ?
C41 C45 H45 120.3 . . ?
C7 O3 C51 117.2(2) . . ?
C15 N5 C9 108.3(2) . . ?
C15 N5 H5 125.9 . . ?
C9 N5 H5 125.9 . . ?
O3 C7 C14 116.1(2) . . ?
O3 C7 C16 124.0(2) . . ?
C14 C7 C16 119.9(2) . . ?
N5 C9 C25 109.1(2) . . ?
N5 C9 C13 119.9(2) . . ?
C25 C9 C13 131.0(2) . . ?
N8 C13 C9 178.4(3) . . ?
C7 C14 C35 120.6(2) . . ?
C7 C14 H14 119.7 . . ?
C35 C14 H14 119.7 . . ?
N5 C15 C29 108.8(2) . . ?
N5 C15 C17 126.2(2) . . ?
C29 C15 C17 124.8(2) . . ?
C7 C16 C30 119.3(2) . . ?
C7 C16 H16 120.4 . . ?
C30 C16 H16 120.4 . . ?
C38 C17 C26 119.8(2) . . ?
C38 C17 C15 123.5(2) . . ?
C26 C17 C15 116.6(2) . . ?
C30 C20 C35 118.2(2) . . ?
C30 C20 C25 121.3(2) . . ?
C35 C20 C25 120.5(2) . . ?
C9 C25 C29 105.3(2) . . ?
C9 C25 C20 125.8(2) . . ?
C29 C25 C20 128.8(2) . . ?
C27 C26 C17 118.5(2) . . ?
C27 C26 C42 121.8(2) . . ?
C17 C26 C42 119.5(2) . . ?
C26 C27 C37 121.0(2) . . ?
C26 C27 H27 119.5 . . ?
C37 C27 H27 119.5 . . ?
C15 C29 C25 108.5(2) . . ?
C15 C29 C46 118.9(2) . . ?
C25 C29 C46 132.6(2) . . ?
C20 C30 C16 121.7(2) . . ?
C20 C30 H30 119.2 . . ?
C16 C30 H30 119.2 . . ?
C14 C35 C20 120.3(2) . . ?
C14 C35 H35 119.8 . . ?
C20 C35 H35 119.8 . . ?
C44 C37 C27 120.3(2) . . ?
C44 C37 H37 119.8 . . ?
C27 C37 H37 119.8 . . ?
C44 C38 C17 120.9(2) . . ?
C44 C38 H38 119.6 . . ?
C17 C38 H38 119.6 . . ?
C26 C42 C46 114.2(2) . . ?
C26 C42 H42A 108.7 . . ?
C46 C42 H42A 108.7 . . ?
C26 C42 H42B 108.7 . . ?
C46 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
C38 C44 C37 119.4(2) . . ?
C38 C44 H44 120.3 . . ?
C37 C44 H44 120.3 . . ?
C29 C46 C42 109.5(2) . . ?
C29 C46 H46A 109.8 . . ?
C42 C46 H46A 109.8 . . ?
C29 C46 H46B 109.8 . . ?
C42 C46 H46B 109.8 . . ?
H46A C46 H46B 108.2 . . ?
O3 C51 H51A 109.5 . . ?
O3 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O3 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 N1 C4 C6 -0.4(3) . . . . ?
C24 N1 C4 C32 179.3(2) . . . . ?
N1 C4 C6 C10 1.1(3) . . . . ?
C32 C4 C6 C10 -178.6(2) . . . . ?
N1 C4 C6 C11 -178.0(2) . . . . ?
C32 C4 C6 C11 2.2(4) . . . . ?
C4 C6 C10 C24 -1.4(3) . . . . ?
C11 C6 C10 C24 177.6(3) . . . . ?
C4 C6 C10 C12 179.3(2) . . . . ?
C11 C6 C10 C12 -1.7(4) . . . . ?
C4 C6 C11 C40 -21.9(3) . . . . ?
C10 C6 C11 C40 159.1(3) . . . . ?
C24 C10 C12 C22 37.3(4) . . . . ?
C6 C10 C12 C22 -143.6(3) . . . . ?
C24 C10 C12 C34 -143.4(3) . . . . ?
C6 C10 C12 C34 35.8(4) . . . . ?
C34 C12 C22 C31 2.2(4) . . . . ?
C10 C12 C22 C31 -178.5(2) . . . . ?
C36 O2 C23 C21 176.8(2) . . . . ?
C36 O2 C23 C31 -2.7(4) . . . . ?
C34 C21 C23 O2 -178.8(2) . . . . ?
C34 C21 C23 C31 0.8(4) . . . . ?
C4 N1 C24 C10 -0.5(3) . . . . ?
C4 N1 C24 C28 176.7(2) . . . . ?
C6 C10 C24 N1 1.2(3) . . . . ?
C12 C10 C24 N1 -179.5(2) . . . . ?
C6 C10 C24 C28 -175.7(3) . . . . ?
C12 C10 C24 C28 3.7(5) . . . . ?
N1 C24 C28 N18 -5(6) . . . . ?
C10 C24 C28 N18 172(6) . . . . ?
O2 C23 C31 C22 179.6(2) . . . . ?
C21 C23 C31 C22 0.1(4) . . . . ?
C12 C22 C31 C23 -1.6(4) . . . . ?
N1 C4 C32 C39 8.9(4) . . . . ?
C6 C4 C32 C39 -171.5(3) . . . . ?
N1 C4 C32 C33 -171.1(2) . . . . ?
C6 C4 C32 C33 8.6(4) . . . . ?
C41 C19 C33 C32 1.4(4) . . . . ?
C41 C19 C33 C40 176.6(3) . . . . ?
C39 C32 C33 C19 -2.3(4) . . . . ?
C4 C32 C33 C19 177.7(2) . . . . ?
C39 C32 C33 C40 -177.5(2) . . . . ?
C4 C32 C33 C40 2.5(3) . . . . ?
C23 C21 C34 C12 -0.2(4) . . . . ?
C22 C12 C34 C21 -1.3(4) . . . . ?
C10 C12 C34 C21 179.4(2) . . . . ?
C33 C32 C39 C45 2.0(4) . . . . ?
C4 C32 C39 C45 -177.9(3) . . . . ?
C19 C33 C40 C11 162.0(2) . . . . ?
C32 C33 C40 C11 -22.9(3) . . . . ?
C6 C11 C40 C33 31.3(3) . . . . ?
C33 C19 C41 C45 -0.3(4) . . . . ?
C32 C39 C45 C41 -0.9(4) . . . . ?
C19 C41 C45 C39 0.0(4) . . . . ?
C51 O3 C7 C14 -178.2(2) . . . . ?
C51 O3 C7 C16 1.2(4) . . . . ?
C15 N5 C9 C25 -0.7(3) . . . . ?
C15 N5 C9 C13 -177.6(2) . . . . ?
N5 C9 C13 N8 -5(10) . . . . ?
C25 C9 C13 N8 179(100) . . . . ?
O3 C7 C14 C35 178.9(2) . . . . ?
C16 C7 C14 C35 -0.6(4) . . . . ?
C9 N5 C15 C29 0.7(3) . . . . ?
C9 N5 C15 C17 -174.3(2) . . . . ?
O3 C7 C16 C30 -178.9(2) . . . . ?
C14 C7 C16 C30 0.5(4) . . . . ?
N5 C15 C17 C38 -16.0(4) . . . . ?
C29 C15 C17 C38 169.7(3) . . . . ?
N5 C15 C17 C26 161.8(2) . . . . ?
C29 C15 C17 C26 -12.4(4) . . . . ?
N5 C9 C25 C29 0.4(3) . . . . ?
C13 C9 C25 C29 176.8(3) . . . . ?
N5 C9 C25 C20 -178.2(2) . . . . ?
C13 C9 C25 C20 -1.7(5) . . . . ?
C30 C20 C25 C9 -34.2(4) . . . . ?
C35 C20 C25 C9 144.5(3) . . . . ?
C30 C20 C25 C29 147.6(3) . . . . ?
C35 C20 C25 C29 -33.8(4) . . . . ?
C38 C17 C26 C27 0.0(4) . . . . ?
C15 C17 C26 C27 -177.9(2) . . . . ?
C38 C17 C26 C42 174.6(2) . . . . ?
C15 C17 C26 C42 -3.3(3) . . . . ?
C17 C26 C27 C37 1.0(4) . . . . ?
C42 C26 C27 C37 -173.5(2) . . . . ?
N5 C15 C29 C25 -0.5(3) . . . . ?
C17 C15 C29 C25 174.7(2) . . . . ?
N5 C15 C29 C46 -179.4(2) . . . . ?
C17 C15 C29 C46 -4.3(4) . . . . ?
C9 C25 C29 C15 0.0(3) . . . . ?
C20 C25 C29 C15 178.6(2) . . . . ?
C9 C25 C29 C46 178.8(3) . . . . ?
C20 C25 C29 C46 -2.7(5) . . . . ?
C35 C20 C30 C16 -0.8(4) . . . . ?
C25 C20 C30 C16 177.8(2) . . . . ?
C7 C16 C30 C20 0.2(4) . . . . ?
C7 C14 C35 C20 -0.1(4) . . . . ?
C30 C20 C35 C14 0.8(4) . . . . ?
C25 C20 C35 C14 -177.9(2) . . . . ?
C26 C27 C37 C44 -1.5(4) . . . . ?
C26 C17 C38 C44 -0.5(4) . . . . ?
C15 C17 C38 C44 177.3(3) . . . . ?
C27 C26 C42 C46 -152.0(2) . . . . ?
C17 C26 C42 C46 33.6(3) . . . . ?
C17 C38 C44 C37 0.0(4) . . . . ?
C27 C37 C44 C38 0.9(4) . . . . ?
C15 C29 C46 C42 33.3(3) . . . . ?
C25 C29 C46 C42 -145.3(3) . . . . ?
C26 C42 C46 C29 -46.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.045
