# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_nacho16
_database_code_depnum_ccdc_archive 'CCDC 1406855'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ; 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H28 N12'
_chemical_formula_sum            'C22 H28 N12'
_chemical_formula_weight         460.56

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.3759(6)
_cell_length_b                   5.9408(3)
_cell_length_c                   37.263(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2296.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    20354
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      26.1

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'

_exptl_special_details           
; 
 ; 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13694
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0841
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         25.740
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4288
_reflns_number_gt                3657
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.992

_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 (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL97

_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)+(0.0777P)²+0.0915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1524 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   2.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4288
_refine_ls_number_parameters     308
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1286
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8076(3) 0.2916(6) 0.41807(8) 0.0558(8) Uani 1 1 d . . . . .
N2 N 0.8856(3) 0.4627(7) 0.40993(9) 0.0643(9) Uani 1 1 d . . . . .
N3 N 0.8323(3) 0.5738(7) 0.38320(9) 0.0608(9) Uani 1 1 d . . . . .
C4 C 0.7203(3) 0.4696(7) 0.37412(10) 0.0481(8) Uani 1 1 d . . . . .
C5 C 0.7030(4) 0.2887(7) 0.39667(10) 0.0516(9) Uani 1 1 d . . . . .
H5 H 0.6331 0.1854 0.3971 0.062 Uiso 1 1 calc R U . . .
C6 C 0.6405(3) 0.5497(6) 0.34280(10) 0.0459(8) Uani 1 1 d . . . . .
C7 C 0.5111(4) 0.4281(7) 0.34108(11) 0.0521(8) Uani 1 1 d . . . . .
H7A H 0.4620 0.4828 0.3204 0.078 Uiso 1 1 calc R U . . .
H7B H 0.4625 0.4575 0.3631 0.078 Uiso 1 1 calc R U . . .
H7C H 0.5257 0.2658 0.3386 0.078 Uiso 1 1 calc R U . . .
C8 C 0.6215(4) 0.8024(7) 0.34423(12) 0.0558(9) Uani 1 1 d . . . . .
H8A H 0.5695 0.8505 0.3237 0.084 Uiso 1 1 calc R U . . .
H8B H 0.7056 0.8773 0.3434 0.084 Uiso 1 1 calc R U . . .
H8C H 0.5772 0.8428 0.3665 0.084 Uiso 1 1 calc R U . . .
N11 N 0.7149(3) 0.4930(5) 0.30954(8) 0.0445(7) Uani 1 1 d . . . . .
N12 N 0.7363(3) 0.2759(5) 0.30139(8) 0.0497(7) Uani 1 1 d . . . . .
N13 N 0.8070(3) 0.2708(5) 0.27189(9) 0.0487(7) Uani 1 1 d . . . . .
C14 C 0.8303(3) 0.4858(6) 0.26148(9) 0.0437(8) Uani 1 1 d . . . . .
C15 C 0.7723(3) 0.6304(6) 0.28529(10) 0.0452(7) Uani 1 1 d . . . . .
H15 H 0.7723 0.7903 0.2849 0.054 Uiso 1 1 calc R U . . .
C16 C 0.9111(3) 0.5381(6) 0.22882(10) 0.0456(8) Uani 1 1 d . . . . .
C17 C 1.0427(3) 0.4272(7) 0.23239(10) 0.0510(9) Uani 1 1 d . . . . .
H17A H 1.0943 0.4600 0.2110 0.076 Uiso 1 1 calc R U . . .
H17B H 1.0319 0.2640 0.2348 0.076 Uiso 1 1 calc R U . . .
H17C H 1.0866 0.4862 0.2537 0.076 Uiso 1 1 calc R U . . .
C18 C 0.9253(4) 0.7906(6) 0.22335(10) 0.0520(9) Uani 1 1 d . . . . .
H18A H 0.9785 0.8191 0.2021 0.078 Uiso 1 1 calc R U . . .
H18B H 0.9667 0.8572 0.2445 0.078 Uiso 1 1 calc R U . . .
H18C H 0.8400 0.8581 0.2200 0.078 Uiso 1 1 calc R U . . .
N21 N 0.8441(3) 0.4417(5) 0.19685(7) 0.0424(7) Uani 1 1 d . . . . .
N22 N 0.7242(3) 0.5114(6) 0.18846(8) 0.0490(7) Uani 1 1 d . . . . .
N23 N 0.6867(3) 0.3930(6) 0.16026(8) 0.0492(7) Uani 1 1 d . . . . .
C24 C 0.7823(3) 0.2481(7) 0.15065(9) 0.0450(8) Uani 1 1 d . . . . .
C25 C 0.8834(3) 0.2785(6) 0.17377(9) 0.0457(8) Uani 1 1 d . . . . .
H25 H 0.9637 0.2019 0.1737 0.055 Uiso 1 1 calc R U . . .
C26 C 0.7702(4) 0.0875(7) 0.11944(9) 0.0499(8) Uani 1 1 d . . . . .
C27 C 0.6349(4) -0.0131(8) 0.11742(12) 0.0592(10) Uani 1 1 d . . . . .
H27A H 0.6299 -0.1168 0.0970 0.089 Uiso 1 1 calc R U . . .
H27B H 0.5718 0.1080 0.1143 0.089 Uiso 1 1 calc R U . . .
H27C H 0.6164 -0.0950 0.1397 0.089 Uiso 1 1 calc R U . . .
C28 C 0.8702(4) -0.0981(7) 0.12173(10) 0.0551(9) Uani 1 1 d . . . . .
H28A H 0.8599 -0.2005 0.1013 0.083 Uiso 1 1 calc R U . . .
H28B H 0.8585 -0.1820 0.1441 0.083 Uiso 1 1 calc R U . . .
H28C H 0.9567 -0.0319 0.1212 0.083 Uiso 1 1 calc R U . . .
N4 N 0.8023(4) 0.2092(6) 0.08499(9) 0.0599(9) Uani 1 1 d . . . . .
N5 N 0.7204(4) 0.3428(7) 0.07489(9) 0.0592(9) Uani 1 1 d . . . . .
N6 N 0.6522(5) 0.4719(9) 0.06280(13) 0.0826(12) Uani 1 1 d . . . . .
C31 C 0.8439(5) 0.1274(9) 0.44613(11) 0.0656(11) Uani 1 1 d . . . . .
H31A H 0.9198 0.1841 0.4595 0.079 Uiso 1 1 calc R U . . .
H31B H 0.8680 -0.0171 0.4347 0.079 Uiso 1 1 calc R U . . .
C32 C 0.7336(4) 0.0890(8) 0.47200(10) 0.0604(10) Uani 1 1 d . . . . .
C33 C 0.6678(6) -0.1111(10) 0.47223(13) 0.0753(13) Uani 1 1 d . . . . .
H33 H 0.6916 -0.2274 0.4560 0.090 Uiso 1 1 calc R U . . .
C34 C 0.5661(6) -0.1449(11) 0.49607(17) 0.0893(16) Uani 1 1 d . . . . .
H34 H 0.5207 -0.2838 0.4963 0.107 Uiso 1 1 calc R U . . .
C35 C 0.5324(6) 0.0256(13) 0.51925(15) 0.0901(18) Uani 1 1 d . . . . .
H35 H 0.4630 0.0036 0.5355 0.108 Uiso 1 1 calc R U . . .
C36 C 0.5977(6) 0.2280(11) 0.51923(12) 0.0807(15) Uani 1 1 d . . . . .
H36 H 0.5733 0.3446 0.5353 0.097 Uiso 1 1 calc R U . . .
C37 C 0.6986(5) 0.2594(9) 0.49571(12) 0.0686(12) Uani 1 1 d . . . . .
H37 H 0.7444 0.3978 0.4957 0.082 Uiso 1 1 calc R U . . .


_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 N2 1.334(5) . ?
N1 C5 1.347(5) . ?
N1 C31 1.479(5) . ?
N2 N3 1.317(5) . ?
N3 C4 1.359(5) . ?
C4 C5 1.376(6) . ?
C4 C6 1.509(5) . ?
C5 H5 0.9500 . ?
C6 N11 1.498(4) . ?
C6 C8 1.515(5) . ?
C6 C7 1.526(5) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
N11 N12 1.344(4) . ?
N11 C15 1.355(5) . ?
N12 N13 1.322(4) . ?
N13 C14 1.356(5) . ?
C14 C15 1.374(5) . ?
C14 C16 1.510(5) . ?
C15 H15 0.9500 . ?
C16 N21 1.493(4) . ?
C16 C18 1.521(5) . ?
C16 C17 1.522(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N21 N22 1.349(4) . ?
N21 C25 1.359(5) . ?
N22 N23 1.323(4) . ?
N23 C24 1.361(5) . ?
C24 C25 1.369(5) . ?
C24 C26 1.510(5) . ?
C25 H25 0.9500 . ?
C26 N4 1.511(5) . ?
C26 C28 1.516(6) . ?
C26 C27 1.528(6) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
N4 N5 1.222(5) . ?
N5 N6 1.137(6) . ?
C31 C32 1.514(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.371(8) . ?
C32 C37 1.392(7) . ?
C33 C34 1.394(8) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(9) . ?
C34 H34 0.9500 . ?
C35 C36 1.380(9) . ?
C35 H35 0.9500 . ?
C36 C37 1.378(7) . ?
C36 H36 0.9500 . ?
C37 H37 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
N2 N1 C5 111.3(3) . . ?
N2 N1 C31 120.6(3) . . ?
C5 N1 C31 128.0(4) . . ?
N3 N2 N1 107.4(3) . . ?
N2 N3 C4 108.6(4) . . ?
N3 C4 C5 108.4(3) . . ?
N3 C4 C6 121.2(3) . . ?
C5 C4 C6 130.3(3) . . ?
N1 C5 C4 104.2(3) . . ?
N1 C5 H5 127.9 . . ?
C4 C5 H5 127.9 . . ?
N11 C6 C4 106.6(3) . . ?
N11 C6 C8 108.6(3) . . ?
C4 C6 C8 110.9(3) . . ?
N11 C6 C7 108.2(3) . . ?
C4 C6 C7 111.5(3) . . ?
C8 C6 C7 110.9(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N12 N11 C15 110.8(3) . . ?
N12 N11 C6 119.2(3) . . ?
C15 N11 C6 130.0(3) . . ?
N13 N12 N11 107.6(3) . . ?
N12 N13 C14 108.4(3) . . ?
N13 C14 C15 109.0(3) . . ?
N13 C14 C16 121.5(3) . . ?
C15 C14 C16 129.4(3) . . ?
N11 C15 C14 104.3(3) . . ?
N11 C15 H15 127.9 . . ?
C14 C15 H15 127.9 . . ?
N21 C16 C14 107.8(3) . . ?
N21 C16 C18 108.5(3) . . ?
C14 C16 C18 111.4(3) . . ?
N21 C16 C17 108.7(3) . . ?
C14 C16 C17 109.8(3) . . ?
C18 C16 C17 110.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N22 N21 C25 110.4(3) . . ?
N22 N21 C16 119.8(3) . . ?
C25 N21 C16 129.7(3) . . ?
N23 N22 N21 107.0(3) . . ?
N22 N23 C24 109.3(3) . . ?
N23 C24 C25 108.0(3) . . ?
N23 C24 C26 122.8(3) . . ?
C25 C24 C26 129.1(3) . . ?
N21 C25 C24 105.2(3) . . ?
N21 C25 H25 127.4 . . ?
C24 C25 H25 127.4 . . ?
C24 C26 N4 109.5(3) . . ?
C24 C26 C28 111.1(3) . . ?
N4 C26 C28 104.2(3) . . ?
C24 C26 C27 111.2(3) . . ?
N4 C26 C27 110.3(3) . . ?
C28 C26 C27 110.3(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N5 N4 C26 114.8(3) . . ?
N6 N5 N4 173.3(5) . . ?
N1 C31 C32 110.9(3) . . ?
N1 C31 H31A 109.5 . . ?
C32 C31 H31A 109.5 . . ?
N1 C31 H31B 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 108.0 . . ?
C33 C32 C37 119.8(5) . . ?
C33 C32 C31 120.7(4) . . ?
C37 C32 C31 119.5(5) . . ?
C32 C33 C34 120.4(5) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C35 C34 C33 119.1(6) . . ?
C35 C34 H34 120.5 . . ?
C33 C34 H34 120.5 . . ?
C34 C35 C36 121.1(5) . . ?
C34 C35 H35 119.5 . . ?
C36 C35 H35 119.5 . . ?
C37 C36 C35 119.4(5) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C32 120.2(5) . . ?
C36 C37 H37 119.9 . . ?
C32 C37 H37 119.9 . . ?

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
C5 N1 N2 N3 0.2(5) . . . . ?
C31 N1 N2 N3 177.1(4) . . . . ?
N1 N2 N3 C4 -0.8(5) . . . . ?
N2 N3 C4 C5 1.1(5) . . . . ?
N2 N3 C4 C6 -176.4(3) . . . . ?
N2 N1 C5 C4 0.4(5) . . . . ?
C31 N1 C5 C4 -176.1(4) . . . . ?
N3 C4 C5 N1 -0.9(4) . . . . ?
C6 C4 C5 N1 176.3(3) . . . . ?
N3 C4 C6 N11 70.0(4) . . . . ?
C5 C4 C6 N11 -106.9(4) . . . . ?
N3 C4 C6 C8 -48.0(5) . . . . ?
C5 C4 C6 C8 135.1(4) . . . . ?
N3 C4 C6 C7 -172.1(4) . . . . ?
C5 C4 C6 C7 11.0(5) . . . . ?
C4 C6 N11 N12 64.6(4) . . . . ?
C8 C6 N11 N12 -175.8(3) . . . . ?
C7 C6 N11 N12 -55.4(4) . . . . ?
C4 C6 N11 C15 -112.5(4) . . . . ?
C8 C6 N11 C15 7.1(5) . . . . ?
C7 C6 N11 C15 127.5(4) . . . . ?
C15 N11 N12 N13 -0.2(4) . . . . ?
C6 N11 N12 N13 -177.8(3) . . . . ?
N11 N12 N13 C14 0.1(4) . . . . ?
N12 N13 C14 C15 0.1(4) . . . . ?
N12 N13 C14 C16 178.9(3) . . . . ?
N12 N11 C15 C14 0.2(4) . . . . ?
C6 N11 C15 C14 177.5(3) . . . . ?
N13 C14 C15 N11 -0.2(4) . . . . ?
C16 C14 C15 N11 -178.8(3) . . . . ?
N13 C14 C16 N21 62.4(4) . . . . ?
C15 C14 C16 N21 -119.0(4) . . . . ?
N13 C14 C16 C18 -178.7(3) . . . . ?
C15 C14 C16 C18 -0.2(5) . . . . ?
N13 C14 C16 C17 -55.9(4) . . . . ?
C15 C14 C16 C17 122.7(4) . . . . ?
C14 C16 N21 N22 59.9(4) . . . . ?
C18 C16 N21 N22 -60.8(4) . . . . ?
C17 C16 N21 N22 178.9(3) . . . . ?
C14 C16 N21 C25 -117.2(4) . . . . ?
C18 C16 N21 C25 122.1(4) . . . . ?
C17 C16 N21 C25 1.8(5) . . . . ?
C25 N21 N22 N23 0.2(4) . . . . ?
C16 N21 N22 N23 -177.4(3) . . . . ?
N21 N22 N23 C24 0.0(4) . . . . ?
N22 N23 C24 C25 -0.2(4) . . . . ?
N22 N23 C24 C26 179.8(3) . . . . ?
N22 N21 C25 C24 -0.3(4) . . . . ?
C16 N21 C25 C24 176.9(3) . . . . ?
N23 C24 C25 N21 0.3(4) . . . . ?
C26 C24 C25 N21 -179.7(3) . . . . ?
N23 C24 C26 N4 82.7(4) . . . . ?
C25 C24 C26 N4 -97.3(5) . . . . ?
N23 C24 C26 C28 -162.7(4) . . . . ?
C25 C24 C26 C28 17.3(6) . . . . ?
N23 C24 C26 C27 -39.4(5) . . . . ?
C25 C24 C26 C27 140.6(4) . . . . ?
C24 C26 N4 N5 -72.6(4) . . . . ?
C28 C26 N4 N5 168.5(4) . . . . ?
C27 C26 N4 N5 50.1(5) . . . . ?
N2 N1 C31 C32 131.9(4) . . . . ?
C5 N1 C31 C32 -51.9(6) . . . . ?
N1 C31 C32 C33 109.4(5) . . . . ?
N1 C31 C32 C37 -70.4(5) . . . . ?
C37 C32 C33 C34 0.0(7) . . . . ?
C31 C32 C33 C34 -179.9(4) . . . . ?
C32 C33 C34 C35 0.3(8) . . . . ?
C33 C34 C35 C36 -0.1(9) . . . . ?
C34 C35 C36 C37 -0.3(8) . . . . ?
C35 C36 C37 C32 0.5(7) . . . . ?
C33 C32 C37 C36 -0.4(7) . . . . ?
C31 C32 C37 C36 179.4(4) . . . . ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_nacho23
_database_code_depnum_ccdc_archive 'CCDC 1406856'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-10-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H39 N15 O2'
_chemical_formula_sum            'C30 H39 N15 O2'
_chemical_formula_weight         641.76

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.8503(9)
_cell_length_b                   11.3224(12)
_cell_length_c                   24.444(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.072(13)
_cell_angle_gamma                90
_cell_volume                     1619.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7219
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      25.7

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.192
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'X-Area (Stoe & Cie, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13020
_diffrn_reflns_av_unetI/netI     0.1510
_diffrn_reflns_av_R_equivalents  0.1567
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.982
_diffrn_reflns_theta_max         25.587
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             5546
_reflns_number_gt                3271
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_max     0.830
_reflns_Friedel_fraction_full    0.858

_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 (Stoe & Cie, 2001)'
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_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)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 994 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -2.4(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5546
_refine_ls_number_parameters     424
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1830
_refine_ls_wR_factor_gt          0.1638
_refine_ls_goodness_of_fit_ref   0.926
_refine_ls_restrained_S_all      0.926
_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
O1 O 1.1549(10) 0.0244(6) 0.1980(3) 0.073(2) Uani 1 1 d . . . . .
H1 H 1.1808 -0.0380 0.2155 0.109 Uiso 1 1 calc R U . . .
O2 O 0.8840(14) 0.0444(6) 0.2601(3) 0.073(2) Uani 1 1 d . . . . .
N1 N 0.3947(9) 0.3120(7) 0.9352(3) 0.0503(18) Uani 1 1 d . . . . .
N2 N 0.3740(10) 0.3818(7) 0.8971(3) 0.0496(18) Uani 1 1 d . . . . .
N3 N 0.3366(13) 0.4474(8) 0.8624(4) 0.071(2) Uani 1 1 d . . . . .
C1 C 0.9852(15) 0.0798(8) 0.2200(5) 0.058(3) Uani 1 1 d . . . . .
C2 C 0.5669(12) 0.2306(8) 0.2501(3) 0.048(2) Uani 1 1 d . . . . .
H2A H 0.4134 0.2612 0.2407 0.058 Uiso 1 1 calc R U . . .
H2B H 0.5554 0.1437 0.2540 0.058 Uiso 1 1 calc R U . . .
C3 C 0.9669(10) 0.3318(6) 0.4281(3) 0.0360(17) Uani 1 1 d . . . . .
C31 C 1.1535(12) 0.2369(8) 0.4251(3) 0.047(2) Uani 1 1 d . . . . .
H31A H 1.2505 0.2514 0.3932 0.070 Uiso 1 1 calc R U . . .
H31B H 1.2470 0.2400 0.4584 0.070 Uiso 1 1 calc R U . . .
H31C H 1.0825 0.1589 0.4220 0.070 Uiso 1 1 calc R U . . .
C32 C 1.0773(12) 0.4527(7) 0.4337(3) 0.0416(18) Uani 1 1 d . . . . .
H32A H 1.1719 0.4686 0.4014 0.062 Uiso 1 1 calc R U . . .
H32B H 0.9581 0.5132 0.4366 0.062 Uiso 1 1 calc R U . . .
H32C H 1.1732 0.4544 0.4666 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4516(10) 0.3438(6) 0.5962(3) 0.0352(17) Uani 1 1 d . . . . .
C41 C 0.2395(12) 0.2611(9) 0.5981(3) 0.056(2) Uani 1 1 d . . . . .
H41A H 0.1456 0.2739 0.5654 0.083 Uiso 1 1 calc R U . . .
H41B H 0.2901 0.1786 0.5992 0.083 Uiso 1 1 calc R U . . .
H41C H 0.1491 0.2787 0.6308 0.083 Uiso 1 1 calc R U . . .
C42 C 0.3804(14) 0.4729(8) 0.5959(4) 0.051(2) Uani 1 1 d . . . . .
H42A H 0.2923 0.4895 0.5626 0.077 Uiso 1 1 calc R U . . .
H42B H 0.2862 0.4894 0.6281 0.077 Uiso 1 1 calc R U . . .
H42C H 0.5170 0.5230 0.5967 0.077 Uiso 1 1 calc R U . . .
C5 C 0.9337(10) 0.1649(7) 0.7494(3) 0.0379(18) Uani 1 1 d . . . . .
C51 C 1.1735(11) 0.2191(8) 0.7563(3) 0.053(2) Uani 1 1 d . . . . .
H51A H 1.2516 0.2200 0.7208 0.079 Uiso 1 1 calc R U . . .
H51B H 1.1594 0.3001 0.7700 0.079 Uiso 1 1 calc R U . . .
H51C H 1.2621 0.1718 0.7823 0.079 Uiso 1 1 calc R U . . .
C52 C 0.9451(14) 0.0416(8) 0.7280(3) 0.051(2) Uani 1 1 d . . . . .
H52A H 1.0176 0.0418 0.6919 0.076 Uiso 1 1 calc R U . . .
H52B H 1.0351 -0.0073 0.7531 0.076 Uiso 1 1 calc R U . . .
H52C H 0.7902 0.0094 0.7250 0.076 Uiso 1 1 calc R U . . .
C6 C 0.6341(11) 0.2574(7) 0.9396(3) 0.0410(19) Uani 1 1 d . . . . .
C7 C 0.7993(12) 0.3563(8) 0.9567(4) 0.050(2) Uani 1 1 d . . . . .
H7A H 0.7547 0.3869 0.9927 0.075 Uiso 1 1 calc R U . . .
H7B H 0.9552 0.3248 0.9587 0.075 Uiso 1 1 calc R U . . .
H7C H 0.7936 0.4202 0.9297 0.075 Uiso 1 1 calc R U . . .
C8 C 0.6018(12) 0.1583(8) 0.9832(3) 0.0448(19) Uani 1 1 d . . . . .
H8 H 0.4937 0.0987 0.9676 0.054 Uiso 1 1 calc R U . . .
C9 C 0.8333(16) 0.0958(9) 0.9926(4) 0.065(3) Uani 1 1 d . . . . .
H9A H 0.8946 0.0690 0.9574 0.097 Uiso 1 1 calc R U . . .
H9B H 0.9410 0.1511 1.0095 0.097 Uiso 1 1 calc R U . . .
H9C H 0.8111 0.0276 1.0167 0.097 Uiso 1 1 calc R U . . .
C10 C 0.5024(16) 0.2008(9) 1.0367(4) 0.066(3) Uani 1 1 d . . . . .
H10A H 0.3559 0.2401 1.0299 0.100 Uiso 1 1 calc R U . . .
H10B H 0.4785 0.1332 1.0611 0.100 Uiso 1 1 calc R U . . .
H10C H 0.6083 0.2566 1.0540 0.100 Uiso 1 1 calc R U . . .
C11 C 0.9270(12) 0.1945(7) 0.1905(3) 0.045(2) Uani 1 1 d . . . . .
C12 C 0.7330(11) 0.2601(7) 0.2044(3) 0.0371(17) Uani 1 1 d . . . . .
C13 C 0.6914(12) 0.3649(7) 0.1756(3) 0.0429(19) Uani 1 1 d . . . . .
H13 H 0.5582 0.4095 0.1839 0.051 Uiso 1 1 calc R U . . .
C14 C 0.8382(14) 0.4053(8) 0.1356(3) 0.049(2) Uani 1 1 d . . . . .
H14 H 0.8055 0.4765 0.1165 0.059 Uiso 1 1 calc R U . . .
C15 C 1.0340(13) 0.3412(8) 0.1234(3) 0.050(2) Uani 1 1 d . . . . .
H15 H 1.1392 0.3690 0.0968 0.060 Uiso 1 1 calc R U . . .
C16 C 1.0731(13) 0.2365(8) 0.1506(4) 0.052(2) Uani 1 1 d . . . . .
H16 H 1.2049 0.1916 0.1416 0.062 Uiso 1 1 calc R U . . .
N21 N 0.6411(9) 0.2821(5) 0.3024(3) 0.0404(16) Uani 1 1 d . . . . .
N22 N 0.5447(10) 0.3802(7) 0.3222(3) 0.0497(17) Uani 1 1 d . . . . .
N23 N 0.6498(10) 0.4088(6) 0.3684(3) 0.0442(16) Uani 1 1 d . . . . .
C24 C 0.8134(10) 0.3257(6) 0.3777(3) 0.0328(16) Uani 1 1 d . . . . .
C25 C 0.8123(12) 0.2455(7) 0.3368(3) 0.046(2) Uani 1 1 d . . . . .
H25 H 0.9087 0.1786 0.3327 0.055 Uiso 1 1 calc R U . . .
N31 N 0.8217(8) 0.3071(5) 0.4774(2) 0.0331(14) Uani 1 1 d . . . . .
N32 N 0.7795(11) 0.1957(6) 0.4919(3) 0.0435(16) Uani 1 1 d . . . . .
N33 N 0.6416(10) 0.1988(5) 0.5343(3) 0.0418(15) Uani 1 1 d . . . . .
C34 C 0.5997(9) 0.3127(6) 0.5480(3) 0.0318(16) Uani 1 1 d . . . . .
C35 C 0.7132(11) 0.3818(6) 0.5111(3) 0.0365(17) Uani 1 1 d . . . . .
H35 H 0.7150 0.4656 0.5097 0.044 Uiso 1 1 calc R U . . .
N41 N 0.5866(8) 0.3193(5) 0.6473(2) 0.0348(14) Uani 1 1 d . . . . .
N42 N 0.6224(14) 0.4053(6) 0.6839(3) 0.064(2) Uani 1 1 d . . . . .
N43 N 0.7457(14) 0.3558(7) 0.7240(3) 0.067(2) Uani 1 1 d . . . . .
C44 C 0.7894(10) 0.2415(6) 0.7119(3) 0.0325(16) Uani 1 1 d . . . . .
C45 C 0.6790(10) 0.2165(6) 0.6644(3) 0.0337(16) Uani 1 1 d . . . . .
H45 H 0.6688 0.1419 0.6468 0.040 Uiso 1 1 calc R U . . .
N51 N 0.8240(8) 0.1659(5) 0.8043(2) 0.0343(14) Uani 1 1 d . . . . .
N52 N 0.6624(11) 0.0861(6) 0.8158(3) 0.0485(17) Uani 1 1 d . . . . .
N53 N 0.5834(11) 0.1111(6) 0.8650(3) 0.0495(18) Uani 1 1 d . . . . .
C54 C 0.6939(10) 0.2078(6) 0.8854(3) 0.0346(16) Uani 1 1 d . . . . .
C55 C 0.8469(10) 0.2421(7) 0.8464(3) 0.0365(17) Uani 1 1 d . . . . .
H55 H 0.9495 0.3070 0.8484 0.044 Uiso 1 1 calc R U . . .


_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 1.292(12) . ?
O1 H1 0.8400 . ?
O2 C1 1.215(12) . ?
N1 N2 1.227(10) . ?
N1 C6 1.535(8) . ?
N2 N3 1.149(11) . ?
C1 C11 1.524(13) . ?
C2 N21 1.470(9) . ?
C2 C12 1.520(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N31 1.502(9) . ?
C3 C32 1.520(10) . ?
C3 C24 1.524(8) . ?
C3 C31 1.533(10) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C4 N41 1.503(7) . ?
C4 C34 1.506(10) . ?
C4 C42 1.520(11) . ?
C4 C41 1.555(10) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C5 N51 1.488(10) . ?
C5 C52 1.492(12) . ?
C5 C44 1.518(9) . ?
C5 C51 1.541(9) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C6 C54 1.481(11) . ?
C6 C7 1.537(10) . ?
C6 C8 1.559(12) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C10 1.512(13) . ?
C8 C9 1.545(11) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.382(13) . ?
C11 C12 1.399(11) . ?
C12 C13 1.401(10) . ?
C13 C14 1.381(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(12) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N21 N22 1.336(9) . ?
N21 C25 1.370(8) . ?
N22 N23 1.325(8) . ?
N23 C24 1.362(9) . ?
C24 C25 1.352(11) . ?
C25 H25 0.9500 . ?
N31 N32 1.332(8) . ?
N31 C35 1.341(9) . ?
N32 N33 1.315(9) . ?
N33 C34 1.354(9) . ?
C34 C35 1.366(10) . ?
C35 H35 0.9500 . ?
N41 N42 1.338(9) . ?
N41 C45 1.349(9) . ?
N42 N43 1.339(9) . ?
N43 C44 1.352(10) . ?
C44 C45 1.356(9) . ?
C45 H45 0.9500 . ?
N51 N52 1.338(9) . ?
N51 C55 1.350(9) . ?
N52 N53 1.320(10) . ?
N53 C54 1.365(9) . ?
C54 C55 1.366(10) . ?
C55 H55 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
C1 O1 H1 109.5 . . ?
N2 N1 C6 113.7(7) . . ?
N3 N2 N1 174.6(8) . . ?
O2 C1 O1 123.5(9) . . ?
O2 C1 C11 123.7(9) . . ?
O1 C1 C11 112.8(10) . . ?
N21 C2 C12 111.3(5) . . ?
N21 C2 H2A 109.4 . . ?
C12 C2 H2A 109.4 . . ?
N21 C2 H2B 109.4 . . ?
C12 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N31 C3 C32 109.7(6) . . ?
N31 C3 C24 107.9(5) . . ?
C32 C3 C24 111.3(6) . . ?
N31 C3 C31 108.1(6) . . ?
C32 C3 C31 109.4(6) . . ?
C24 C3 C31 110.4(6) . . ?
C3 C31 H31A 109.5 . . ?
C3 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C3 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C3 C32 H32A 109.5 . . ?
C3 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C3 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N41 C4 C34 107.8(5) . . ?
N41 C4 C42 109.0(6) . . ?
C34 C4 C42 112.2(6) . . ?
N41 C4 C41 106.4(6) . . ?
C34 C4 C41 110.0(6) . . ?
C42 C4 C41 111.1(7) . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C4 C42 H42A 109.5 . . ?
C4 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C4 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N51 C5 C52 110.0(7) . . ?
N51 C5 C44 107.5(5) . . ?
C52 C5 C44 110.4(6) . . ?
N51 C5 C51 107.0(6) . . ?
C52 C5 C51 111.7(6) . . ?
C44 C5 C51 110.1(7) . . ?
C5 C51 H51A 109.5 . . ?
C5 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C5 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C5 C52 H52A 109.5 . . ?
C5 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C5 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C54 C6 N1 107.9(5) . . ?
C54 C6 C7 111.8(6) . . ?
N1 C6 C7 107.4(6) . . ?
C54 C6 C8 111.5(6) . . ?
N1 C6 C8 103.1(6) . . ?
C7 C6 C8 114.5(6) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C8 C9 110.8(7) . . ?
C10 C8 C6 114.2(7) . . ?
C9 C8 C6 108.9(7) . . ?
C10 C8 H8 107.5 . . ?
C9 C8 H8 107.5 . . ?
C6 C8 H8 107.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 119.5(7) . . ?
C16 C11 C1 119.3(8) . . ?
C12 C11 C1 121.2(8) . . ?
C11 C12 C13 117.9(7) . . ?
C11 C12 C2 125.6(7) . . ?
C13 C12 C2 116.4(7) . . ?
C14 C13 C12 121.9(7) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.5(8) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.9(8) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C11 122.3(8) . . ?
C15 C16 H16 118.9 . . ?
C11 C16 H16 118.9 . . ?
N22 N21 C25 109.8(6) . . ?
N22 N21 C2 121.3(5) . . ?
C25 N21 C2 128.9(7) . . ?
N23 N22 N21 108.3(5) . . ?
N22 N23 C24 107.5(6) . . ?
C25 C24 N23 109.7(5) . . ?
C25 C24 C3 129.1(6) . . ?
N23 C24 C3 121.2(6) . . ?
C24 C25 N21 104.7(7) . . ?
C24 C25 H25 127.6 . . ?
N21 C25 H25 127.6 . . ?
N32 N31 C35 110.2(6) . . ?
N32 N31 C3 119.6(6) . . ?
C35 N31 C3 130.1(6) . . ?
N33 N32 N31 107.3(6) . . ?
N32 N33 C34 109.4(6) . . ?
N33 C34 C35 107.1(7) . . ?
N33 C34 C4 121.4(6) . . ?
C35 C34 C4 131.5(7) . . ?
N31 C35 C34 105.9(6) . . ?
N31 C35 H35 127.0 . . ?
C34 C35 H35 127.0 . . ?
N42 N41 C45 111.0(5) . . ?
N42 N41 C4 120.2(6) . . ?
C45 N41 C4 128.8(6) . . ?
N41 N42 N43 105.5(6) . . ?
N42 N43 C44 110.1(6) . . ?
N43 C44 C45 107.2(6) . . ?
N43 C44 C5 121.3(6) . . ?
C45 C44 C5 131.4(7) . . ?
N41 C45 C44 106.0(6) . . ?
N41 C45 H45 127.0 . . ?
C44 C45 H45 127.0 . . ?
N52 N51 C55 109.9(6) . . ?
N52 N51 C5 119.4(6) . . ?
C55 N51 C5 130.5(6) . . ?
N53 N52 N51 107.2(6) . . ?
N52 N53 C54 109.8(7) . . ?
N53 C54 C55 106.5(7) . . ?
N53 C54 C6 121.2(7) . . ?
C55 C54 C6 132.3(6) . . ?
N51 C55 C54 106.6(6) . . ?
N51 C55 H55 126.7 . . ?
C54 C55 H55 126.7 . . ?

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
N2 N1 C6 C54 -52.2(9) . . . . ?
N2 N1 C6 C7 68.4(9) . . . . ?
N2 N1 C6 C8 -170.3(7) . . . . ?
C54 C6 C8 C10 -170.3(6) . . . . ?
N1 C6 C8 C10 -54.8(8) . . . . ?
C7 C6 C8 C10 61.6(8) . . . . ?
C54 C6 C8 C9 65.3(8) . . . . ?
N1 C6 C8 C9 -179.3(7) . . . . ?
C7 C6 C8 C9 -62.9(9) . . . . ?
O2 C1 C11 C16 170.1(8) . . . . ?
O1 C1 C11 C16 -9.5(9) . . . . ?
O2 C1 C11 C12 -7.6(11) . . . . ?
O1 C1 C11 C12 172.8(6) . . . . ?
C16 C11 C12 C13 2.0(9) . . . . ?
C1 C11 C12 C13 179.7(6) . . . . ?
C16 C11 C12 C2 -175.1(6) . . . . ?
C1 C11 C12 C2 2.6(10) . . . . ?
N21 C2 C12 C11 87.8(9) . . . . ?
N21 C2 C12 C13 -89.3(7) . . . . ?
C11 C12 C13 C14 -1.6(10) . . . . ?
C2 C12 C13 C14 175.7(6) . . . . ?
C12 C13 C14 C15 -0.4(11) . . . . ?
C13 C14 C15 C16 2.0(11) . . . . ?
C14 C15 C16 C11 -1.6(11) . . . . ?
C12 C11 C16 C15 -0.4(10) . . . . ?
C1 C11 C16 C15 -178.2(7) . . . . ?
C12 C2 N21 N22 101.9(8) . . . . ?
C12 C2 N21 C25 -75.7(10) . . . . ?
C25 N21 N22 N23 0.3(8) . . . . ?
C2 N21 N22 N23 -177.7(7) . . . . ?
N21 N22 N23 C24 -0.6(8) . . . . ?
N22 N23 C24 C25 0.7(9) . . . . ?
N22 N23 C24 C3 -179.8(6) . . . . ?
N31 C3 C24 C25 -111.8(8) . . . . ?
C32 C3 C24 C25 127.9(8) . . . . ?
C31 C3 C24 C25 6.2(11) . . . . ?
N31 C3 C24 N23 68.9(8) . . . . ?
C32 C3 C24 N23 -51.5(9) . . . . ?
C31 C3 C24 N23 -173.2(7) . . . . ?
N23 C24 C25 N21 -0.5(9) . . . . ?
C3 C24 C25 N21 -179.9(7) . . . . ?
N22 N21 C25 C24 0.1(8) . . . . ?
C2 N21 C25 C24 178.0(7) . . . . ?
C32 C3 N31 N32 -154.9(5) . . . . ?
C24 C3 N31 N32 83.8(7) . . . . ?
C31 C3 N31 N32 -35.6(7) . . . . ?
C32 C3 N31 C35 27.5(8) . . . . ?
C24 C3 N31 C35 -93.8(7) . . . . ?
C31 C3 N31 C35 146.8(6) . . . . ?
C35 N31 N32 N33 0.9(7) . . . . ?
C3 N31 N32 N33 -177.1(5) . . . . ?
N31 N32 N33 C34 -1.6(7) . . . . ?
N32 N33 C34 C35 1.6(7) . . . . ?
N32 N33 C34 C4 -178.3(5) . . . . ?
N41 C4 C34 N33 74.0(7) . . . . ?
C42 C4 C34 N33 -166.0(6) . . . . ?
C41 C4 C34 N33 -41.7(8) . . . . ?
N41 C4 C34 C35 -105.9(7) . . . . ?
C42 C4 C34 C35 14.1(8) . . . . ?
C41 C4 C34 C35 138.4(7) . . . . ?
N32 N31 C35 C34 0.1(6) . . . . ?
C3 N31 C35 C34 177.9(5) . . . . ?
N33 C34 C35 N31 -1.0(6) . . . . ?
C4 C34 C35 N31 178.9(5) . . . . ?
C34 C4 N41 N42 123.1(7) . . . . ?
C42 C4 N41 N42 1.1(9) . . . . ?
C41 C4 N41 N42 -118.9(8) . . . . ?
C34 C4 N41 C45 -59.1(9) . . . . ?
C42 C4 N41 C45 178.8(7) . . . . ?
C41 C4 N41 C45 58.9(9) . . . . ?
C45 N41 N42 N43 1.8(9) . . . . ?
C4 N41 N42 N43 179.9(6) . . . . ?
N41 N42 N43 C44 1.2(10) . . . . ?
N42 N43 C44 C45 -3.7(10) . . . . ?
N42 N43 C44 C5 177.8(7) . . . . ?
N51 C5 C44 N43 57.1(9) . . . . ?
C52 C5 C44 N43 177.1(8) . . . . ?
C51 C5 C44 N43 -59.1(10) . . . . ?
N51 C5 C44 C45 -121.0(8) . . . . ?
C52 C5 C44 C45 -1.0(11) . . . . ?
C51 C5 C44 C45 122.8(9) . . . . ?
N42 N41 C45 C44 -4.0(8) . . . . ?
C4 N41 C45 C44 178.1(6) . . . . ?
N43 C44 C45 N41 4.6(8) . . . . ?
C5 C44 C45 N41 -177.1(7) . . . . ?
C52 C5 N51 N52 -32.0(7) . . . . ?
C44 C5 N51 N52 88.2(7) . . . . ?
C51 C5 N51 N52 -153.6(6) . . . . ?
C52 C5 N51 C55 153.4(6) . . . . ?
C44 C5 N51 C55 -86.4(7) . . . . ?
C51 C5 N51 C55 31.8(9) . . . . ?
C55 N51 N52 N53 -0.2(8) . . . . ?
C5 N51 N52 N53 -175.8(6) . . . . ?
N51 N52 N53 C54 0.2(8) . . . . ?
N52 N53 C54 C55 -0.1(8) . . . . ?
N52 N53 C54 C6 178.3(6) . . . . ?
N1 C6 C54 N53 -68.9(8) . . . . ?
C7 C6 C54 N53 173.2(6) . . . . ?
C8 C6 C54 N53 43.6(8) . . . . ?
N1 C6 C54 C55 109.0(8) . . . . ?
C7 C6 C54 C55 -8.9(10) . . . . ?
C8 C6 C54 C55 -138.5(7) . . . . ?
N52 N51 C55 C54 0.2(7) . . . . ?
C5 N51 C55 C54 175.2(6) . . . . ?
N53 C54 C55 N51 0.0(7) . . . . ?
C6 C54 C55 N51 -178.1(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 N43 0.84 1.95 2.761(10) 160.6 2_746

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.075

_shelxl_version_number           2014/6

