 
data_mo_dd20133_0m 
  
_audit_creation_method            SHELXL-2013 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C36 H32 N4 O' 
_chemical_formula_weight          536.65 
  
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                    12.6111(5) 
_cell_length_b                    7.5598(3) 
_cell_length_c                    15.0851(6) 
_cell_angle_alpha                 90 
_cell_angle_beta                  100.8860(10) 
_cell_angle_gamma                 90 
_cell_volume                      1412.29(10) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     9986 
_cell_measurement_theta_min       5.500 
_cell_measurement_theta_max       53.811 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.262 
_exptl_crystal_F_000              568 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.190 
_exptl_crystal_size_mid           0.140 
_exptl_crystal_size_min           0.070 
_exptl_absorpt_coefficient_mu     0.077 
_shelx_estimated_absorpt_T_min    0.985 
_shelx_estimated_absorpt_T_max    0.995 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6042 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             29614 
_diffrn_reflns_av_unetI/netI      0.0345 
_diffrn_reflns_av_R_equivalents   0.0509 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.926 
_diffrn_reflns_theta_max          25.999 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.995 
_diffrn_measured_fraction_theta_full  0.995 
_diffrn_reflns_Laue_measured_fraction_max    0.995 
_diffrn_reflns_Laue_measured_fraction_full   0.995 
_diffrn_reflns_point_group_measured_fraction_max   0.996 
_diffrn_reflns_point_group_measured_fraction_full  0.995 
_reflns_number_total              5534 
_reflns_number_gt                 4832 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.852 
_reflns_Friedel_fraction_max      0.996 
_reflns_Friedel_fraction_full     0.996 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 ? 
; 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0464P)²+0.1358P] 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        0.051(7) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1979 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
; 
_refine_ls_abs_structure_Flack    -1.1(7) 
_chemical_absolute_configuration  unk 
_refine_ls_number_reflns          5534 
_refine_ls_number_parameters      374 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0469 
_refine_ls_R_factor_gt            0.0379 
_refine_ls_wR_factor_ref          0.0981 
_refine_ls_wR_factor_gt           0.0910 
_refine_ls_goodness_of_fit_ref    1.053 
_refine_ls_restrained_S_all       1.052 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
  
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.96931(13) 0.5521(3) 0.91434(10) 0.0508(4) Uani 1 1 d . . . . . 
N1 N 0.99267(16) 0.6285(3) 0.63636(13) 0.0467(5) Uani 1 1 d . . . . . 
N2 N 0.7719(2) 0.5096(5) 1.03753(16) 0.0862(10) Uani 1 1 d . . . . . 
N3 N 1.09166(15) 0.5674(3) 0.77774(13) 0.0468(5) Uani 1 1 d . . . . . 
N4 N 0.43139(15) 0.5570(3) 0.30821(12) 0.0453(5) Uani 1 1 d . . . . . 
C1 C 0.8989(2) 0.6344(4) 0.57493(16) 0.0463(6) Uani 1 1 d . . . . . 
C2 C 0.80055(18) 0.5875(3) 0.59474(14) 0.0405(5) Uani 1 1 d . . . . . 
C3 C 0.79473(18) 0.5561(3) 0.68667(14) 0.0381(5) Uani 1 1 d . . . . . 
C4 C 0.69499(19) 0.5303(3) 0.71489(15) 0.0436(5) Uani 1 1 d . . . . . 
H4 H 0.6327 0.5213 0.6709 0.052 Uiso 1 1 calc R U . . . 
C5 C 0.6854(2) 0.5179(4) 0.80299(16) 0.0466(6) Uani 1 1 d . . . . . 
C6 C 0.7817(2) 0.5289(4) 0.86831(14) 0.0457(6) Uani 1 1 d . . . . . 
C7 C 0.88162(19) 0.5486(3) 0.84473(14) 0.0420(5) Uani 1 1 d . . . . . 
C8 C 0.89227(17) 0.5582(3) 0.75285(14) 0.0382(5) Uani 1 1 d . . . . . 
C9 C 0.99209(18) 0.5822(3) 0.72045(15) 0.0413(5) Uani 1 1 d . . . . . 
C10 C 0.9120(2) 0.6924(5) 0.48262(18) 0.0680(9) Uani 1 1 d . . . . . 
H10A H 0.9670 0.7816 0.4879 0.102 Uiso 1 1 calc R U . . . 
H10B H 0.8449 0.7400 0.4508 0.102 Uiso 1 1 calc R U . . . 
H10C H 0.9324 0.5929 0.4500 0.102 Uiso 1 1 calc R U . . . 
C11 C 0.5782(2) 0.4985(5) 0.83068(19) 0.0637(8) Uani 1 1 d . . . . . 
H11A H 0.5620 0.6043 0.8607 0.096 Uiso 1 1 calc R U . . . 
H11B H 0.5804 0.3996 0.8710 0.096 Uiso 1 1 calc R U . . . 
H11C H 0.5233 0.4790 0.7782 0.096 Uiso 1 1 calc R U . . . 
C12 C 0.7770(2) 0.5191(4) 0.96303(17) 0.0586(7) Uani 1 1 d . . . . . 
C13 C 1.1205(2) 0.3966(4) 0.82216(15) 0.0463(6) Uani 1 1 d . . . . . 
H13A H 1.0555 0.3382 0.8326 0.056 Uiso 1 1 calc R U . . . 
H13B H 1.1669 0.4166 0.8803 0.056 Uiso 1 1 calc R U . . . 
C14 C 1.1780(2) 0.2776(4) 0.76528(18) 0.0535(7) Uani 1 1 d . . . . . 
H14A H 1.1285 0.2461 0.7102 0.064 Uiso 1 1 calc R U . . . 
H14B H 1.2000 0.1694 0.7983 0.064 Uiso 1 1 calc R U . . . 
C15 C 1.2770(2) 0.3674(5) 0.7413(2) 0.0644(8) Uani 1 1 d . . . . . 
H15A H 1.3306 0.3862 0.7957 0.077 Uiso 1 1 calc R U . . . 
H15B H 1.3085 0.2919 0.7012 0.077 Uiso 1 1 calc R U . . . 
C16 C 1.2456(2) 0.5426(5) 0.6959(2) 0.0660(8) Uani 1 1 d . . . . . 
H16A H 1.2007 0.5220 0.6372 0.079 Uiso 1 1 calc R U . . . 
H16B H 1.3101 0.6044 0.6869 0.079 Uiso 1 1 calc R U . . . 
C17 C 1.1847(2) 0.6566(4) 0.7522(2) 0.0605(7) Uani 1 1 d . . . . . 
H17A H 1.2339 0.6927 0.8067 0.073 Uiso 1 1 calc R U . . . 
H17B H 1.1598 0.7626 0.7184 0.073 Uiso 1 1 calc R U . . . 
C18 C 1.0056(3) 0.7240(4) 0.9450(2) 0.0803(11) Uani 1 1 d . . . . . 
H18A H 1.0288 0.7872 0.8969 0.120 Uiso 1 1 calc R U . . . 
H18B H 1.0649 0.7133 0.9950 0.120 Uiso 1 1 calc R U . . . 
H18C H 0.9476 0.7871 0.9638 0.120 Uiso 1 1 calc R U . . . 
C19 C 0.70205(18) 0.5783(3) 0.52175(14) 0.0407(5) Uani 1 1 d . . . . . 
C20 C 0.69316(19) 0.4491(3) 0.45462(15) 0.0434(6) Uani 1 1 d . . . . . 
H20 H 0.7485 0.3672 0.4562 0.052 Uiso 1 1 calc R U . . . 
C21 C 0.60395(19) 0.4403(3) 0.38587(15) 0.0440(6) Uani 1 1 d . . . . . 
H21 H 0.5988 0.3506 0.3431 0.053 Uiso 1 1 calc R U . . . 
C22 C 0.52211(17) 0.5642(3) 0.38016(14) 0.0400(5) Uani 1 1 d . . . . . 
C23 C 0.5297(2) 0.6943(3) 0.44572(16) 0.0453(6) Uani 1 1 d . . . . . 
H23 H 0.4757 0.7792 0.4426 0.054 Uiso 1 1 calc R U . . . 
C24 C 0.6176(2) 0.6975(3) 0.51574(16) 0.0455(6) Uani 1 1 d . . . . . 
H24 H 0.6203 0.7828 0.5605 0.055 Uiso 1 1 calc R U . . . 
C25 C 0.4352(2) 0.5270(4) 0.21705(15) 0.0475(6) Uani 1 1 d . . . . . 
C26 C 0.5229(2) 0.5117(5) 0.17502(17) 0.0604(8) Uani 1 1 d . . . . . 
H26 H 0.5931 0.5170 0.2078 0.073 Uiso 1 1 calc R U . . . 
C27 C 0.5027(3) 0.4885(6) 0.08288(19) 0.0856(12) Uani 1 1 d . . . . . 
H27 H 0.5604 0.4780 0.0529 0.103 Uiso 1 1 calc R U . . . 
C28 C 0.3983(3) 0.4803(7) 0.0340(2) 0.0997(15) Uani 1 1 d . . . . . 
H28 H 0.3871 0.4627 -0.0281 0.120 Uiso 1 1 calc R U . . . 
C29 C 0.3116(3) 0.4978(6) 0.07517(19) 0.0802(11) Uani 1 1 d . . . . . 
H29 H 0.2418 0.4935 0.0415 0.096 Uiso 1 1 calc R U . . . 
C30 C 0.3287(2) 0.5222(4) 0.16840(16) 0.0538(6) Uani 1 1 d . . . . . 
C31 C 0.2579(2) 0.5473(4) 0.23130(17) 0.0502(6) Uani 1 1 d . . . . . 
C32 C 0.1456(2) 0.5500(4) 0.2237(2) 0.0663(8) Uani 1 1 d . . . . . 
H32 H 0.1006 0.5388 0.1675 0.080 Uiso 1 1 calc R U . . . 
C33 C 0.1027(2) 0.5694(5) 0.3003(3) 0.0714(9) Uani 1 1 d . . . . . 
H33 H 0.0281 0.5689 0.2959 0.086 Uiso 1 1 calc R U . . . 
C34 C 0.1684(2) 0.5895(4) 0.3834(2) 0.0669(8) Uani 1 1 d . . . . . 
H34 H 0.1371 0.6028 0.4341 0.080 Uiso 1 1 calc R U . . . 
C35 C 0.2790(2) 0.5905(4) 0.39371(19) 0.0533(6) Uani 1 1 d . . . . . 
H35 H 0.3228 0.6050 0.4502 0.064 Uiso 1 1 calc R U . . . 
C36 C 0.32307(18) 0.5690(3) 0.31684(16) 0.0433(5) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C7 1.374(3) . ? 
O1 C18 1.426(4) . ? 
N1 C9 1.317(3) . ? 
N1 C1 1.358(3) . ? 
N2 C12 1.140(3) . ? 
N3 C9 1.388(3) . ? 
N3 C17 1.466(3) . ? 
N3 C13 1.468(3) . ? 
N4 C36 1.399(3) . ? 
N4 C25 1.404(3) . ? 
N4 C22 1.422(3) . ? 
C1 C2 1.376(3) . ? 
C1 C10 1.499(3) . ? 
C2 C3 1.422(3) . ? 
C2 C19 1.498(3) . ? 
C3 C4 1.416(3) . ? 
C3 C8 1.430(3) . ? 
C4 C5 1.360(3) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.415(3) . ? 
C5 C11 1.496(3) . ? 
C6 C7 1.380(3) . ? 
C6 C12 1.443(3) . ? 
C7 C8 1.419(3) . ? 
C8 C9 1.445(3) . ? 
C10 H10A 0.9600 . ? 
C10 H10B 0.9600 . ? 
C10 H10C 0.9600 . ? 
C11 H11A 0.9600 . ? 
C11 H11B 0.9600 . ? 
C11 H11C 0.9600 . ? 
C13 C14 1.519(4) . ? 
C13 H13A 0.9700 . ? 
C13 H13B 0.9700 . ? 
C14 C15 1.523(4) . ? 
C14 H14A 0.9700 . ? 
C14 H14B 0.9700 . ? 
C15 C16 1.509(5) . ? 
C15 H15A 0.9700 . ? 
C15 H15B 0.9700 . ? 
C16 C17 1.517(5) . ? 
C16 H16A 0.9700 . ? 
C16 H16B 0.9700 . ? 
C17 H17A 0.9700 . ? 
C17 H17B 0.9700 . ? 
C18 H18A 0.9600 . ? 
C18 H18B 0.9600 . ? 
C18 H18C 0.9600 . ? 
C19 C24 1.385(3) . ? 
C19 C20 1.396(3) . ? 
C20 C21 1.380(3) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.384(3) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.386(3) . ? 
C23 C24 1.380(3) . ? 
C23 H23 0.9300 . ? 
C24 H24 0.9300 . ? 
C25 C26 1.380(4) . ? 
C25 C30 1.404(3) . ? 
C26 C27 1.376(4) . ? 
C26 H26 0.9300 . ? 
C27 C28 1.384(5) . ? 
C27 H27 0.9300 . ? 
C28 C29 1.362(5) . ? 
C28 H28 0.9300 . ? 
C29 C30 1.394(4) . ? 
C29 H29 0.9300 . ? 
C30 C31 1.433(4) . ? 
C31 C32 1.399(4) . ? 
C31 C36 1.402(3) . ? 
C32 C33 1.375(5) . ? 
C32 H32 0.9300 . ? 
C33 C34 1.374(4) . ? 
C33 H33 0.9300 . ? 
C34 C35 1.374(4) . ? 
C34 H34 0.9300 . ? 
C35 C36 1.387(4) . ? 
C35 H35 0.9300 . ? 
  
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C7 O1 C18 115.4(2) . . ? 
C9 N1 C1 120.2(2) . . ? 
C9 N3 C17 118.3(2) . . ? 
C9 N3 C13 118.1(2) . . ? 
C17 N3 C13 112.5(2) . . ? 
C36 N4 C25 108.45(18) . . ? 
C36 N4 C22 125.84(18) . . ? 
C25 N4 C22 125.63(19) . . ? 
N1 C1 C2 123.2(2) . . ? 
N1 C1 C10 114.1(2) . . ? 
C2 C1 C10 122.6(2) . . ? 
C1 C2 C3 118.0(2) . . ? 
C1 C2 C19 120.58(19) . . ? 
C3 C2 C19 121.37(19) . . ? 
C4 C3 C2 121.91(19) . . ? 
C4 C3 C8 119.17(18) . . ? 
C2 C3 C8 118.87(19) . . ? 
C5 C4 C3 123.5(2) . . ? 
C5 C4 H4 118.3 . . ? 
C3 C4 H4 118.3 . . ? 
C4 C5 C6 117.0(2) . . ? 
C4 C5 C11 122.1(2) . . ? 
C6 C5 C11 120.9(2) . . ? 
C7 C6 C5 122.2(2) . . ? 
C7 C6 C12 118.1(2) . . ? 
C5 C6 C12 119.7(2) . . ? 
O1 C7 C6 116.56(19) . . ? 
O1 C7 C8 122.3(2) . . ? 
C6 C7 C8 121.10(19) . . ? 
C7 C8 C3 116.97(19) . . ? 
C7 C8 C9 125.85(19) . . ? 
C3 C8 C9 117.03(18) . . ? 
N1 C9 N3 116.9(2) . . ? 
N1 C9 C8 121.5(2) . . ? 
N3 C9 C8 121.52(19) . . ? 
C1 C10 H10A 109.5 . . ? 
C1 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
C1 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
C5 C11 H11A 109.5 . . ? 
C5 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C5 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
N2 C12 C6 178.9(4) . . ? 
N3 C13 C14 111.5(2) . . ? 
N3 C13 H13A 109.3 . . ? 
C14 C13 H13A 109.3 . . ? 
N3 C13 H13B 109.3 . . ? 
C14 C13 H13B 109.3 . . ? 
H13A C13 H13B 108.0 . . ? 
C13 C14 C15 111.7(3) . . ? 
C13 C14 H14A 109.3 . . ? 
C15 C14 H14A 109.3 . . ? 
C13 C14 H14B 109.3 . . ? 
C15 C14 H14B 109.3 . . ? 
H14A C14 H14B 107.9 . . ? 
C16 C15 C14 110.0(2) . . ? 
C16 C15 H15A 109.7 . . ? 
C14 C15 H15A 109.7 . . ? 
C16 C15 H15B 109.7 . . ? 
C14 C15 H15B 109.7 . . ? 
H15A C15 H15B 108.2 . . ? 
C15 C16 C17 111.2(3) . . ? 
C15 C16 H16A 109.4 . . ? 
C17 C16 H16A 109.4 . . ? 
C15 C16 H16B 109.4 . . ? 
C17 C16 H16B 109.4 . . ? 
H16A C16 H16B 108.0 . . ? 
N3 C17 C16 113.6(3) . . ? 
N3 C17 H17A 108.8 . . ? 
C16 C17 H17A 108.8 . . ? 
N3 C17 H17B 108.8 . . ? 
C16 C17 H17B 108.8 . . ? 
H17A C17 H17B 107.7 . . ? 
O1 C18 H18A 109.5 . . ? 
O1 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
O1 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C24 C19 C20 116.9(2) . . ? 
C24 C19 C2 122.6(2) . . ? 
C20 C19 C2 120.5(2) . . ? 
C21 C20 C19 121.4(2) . . ? 
C21 C20 H20 119.3 . . ? 
C19 C20 H20 119.3 . . ? 
C20 C21 C22 120.5(2) . . ? 
C20 C21 H21 119.8 . . ? 
C22 C21 H21 119.8 . . ? 
C21 C22 C23 119.1(2) . . ? 
C21 C22 N4 120.3(2) . . ? 
C23 C22 N4 120.6(2) . . ? 
C24 C23 C22 119.7(2) . . ? 
C24 C23 H23 120.2 . . ? 
C22 C23 H23 120.2 . . ? 
C23 C24 C19 122.4(2) . . ? 
C23 C24 H24 118.8 . . ? 
C19 C24 H24 118.8 . . ? 
C26 C25 N4 130.0(2) . . ? 
C26 C25 C30 121.9(2) . . ? 
N4 C25 C30 108.0(2) . . ? 
C27 C26 C25 117.6(3) . . ? 
C27 C26 H26 121.2 . . ? 
C25 C26 H26 121.2 . . ? 
C26 C27 C28 121.3(3) . . ? 
C26 C27 H27 119.3 . . ? 
C28 C27 H27 119.3 . . ? 
C29 C28 C27 121.2(3) . . ? 
C29 C28 H28 119.4 . . ? 
C27 C28 H28 119.4 . . ? 
C28 C29 C30 119.2(3) . . ? 
C28 C29 H29 120.4 . . ? 
C30 C29 H29 120.4 . . ? 
C29 C30 C25 118.8(3) . . ? 
C29 C30 C31 133.5(3) . . ? 
C25 C30 C31 107.7(2) . . ? 
C32 C31 C36 118.8(3) . . ? 
C32 C31 C30 134.0(2) . . ? 
C36 C31 C30 107.1(2) . . ? 
C33 C32 C31 119.0(3) . . ? 
C33 C32 H32 120.5 . . ? 
C31 C32 H32 120.5 . . ? 
C34 C33 C32 120.9(3) . . ? 
C34 C33 H33 119.5 . . ? 
C32 C33 H33 119.5 . . ? 
C33 C34 C35 121.9(3) . . ? 
C33 C34 H34 119.1 . . ? 
C35 C34 H34 119.1 . . ? 
C34 C35 C36 117.6(3) . . ? 
C34 C35 H35 121.2 . . ? 
C36 C35 H35 121.2 . . ? 
C35 C36 N4 129.6(2) . . ? 
C35 C36 C31 121.7(2) . . ? 
N4 C36 C31 108.6(2) . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C9 N1 C1 C2 -2.5(4) . . . . ? 
C9 N1 C1 C10 178.9(3) . . . . ? 
N1 C1 C2 C3 9.3(4) . . . . ? 
C10 C1 C2 C3 -172.2(3) . . . . ? 
N1 C1 C2 C19 -173.4(2) . . . . ? 
C10 C1 C2 C19 5.1(4) . . . . ? 
C1 C2 C3 C4 171.5(2) . . . . ? 
C19 C2 C3 C4 -5.7(4) . . . . ? 
C1 C2 C3 C8 -5.8(3) . . . . ? 
C19 C2 C3 C8 177.0(2) . . . . ? 
C2 C3 C4 C5 -173.1(2) . . . . ? 
C8 C3 C4 C5 4.2(4) . . . . ? 
C3 C4 C5 C6 -1.1(4) . . . . ? 
C3 C4 C5 C11 177.3(3) . . . . ? 
C4 C5 C6 C7 -1.0(4) . . . . ? 
C11 C5 C6 C7 -179.3(3) . . . . ? 
C4 C5 C6 C12 179.2(3) . . . . ? 
C11 C5 C6 C12 0.8(4) . . . . ? 
C18 O1 C7 C6 -95.4(3) . . . . ? 
C18 O1 C7 C8 86.8(3) . . . . ? 
C5 C6 C7 O1 -178.1(2) . . . . ? 
C12 C6 C7 O1 1.8(4) . . . . ? 
C5 C6 C7 C8 -0.2(4) . . . . ? 
C12 C6 C7 C8 179.7(2) . . . . ? 
O1 C7 C8 C3 -179.0(2) . . . . ? 
C6 C7 C8 C3 3.3(3) . . . . ? 
O1 C7 C8 C9 -3.6(4) . . . . ? 
C6 C7 C8 C9 178.7(2) . . . . ? 
C4 C3 C8 C7 -5.1(3) . . . . ? 
C2 C3 C8 C7 172.3(2) . . . . ? 
C4 C3 C8 C9 179.0(2) . . . . ? 
C2 C3 C8 C9 -3.6(3) . . . . ? 
C1 N1 C9 N3 175.7(2) . . . . ? 
C1 N1 C9 C8 -7.9(4) . . . . ? 
C17 N3 C9 N1 19.6(3) . . . . ? 
C13 N3 C9 N1 -121.8(2) . . . . ? 
C17 N3 C9 C8 -156.8(2) . . . . ? 
C13 N3 C9 C8 61.8(3) . . . . ? 
C7 C8 C9 N1 -164.7(2) . . . . ? 
C3 C8 C9 N1 10.7(3) . . . . ? 
C7 C8 C9 N3 11.5(4) . . . . ? 
C3 C8 C9 N3 -173.0(2) . . . . ? 
C9 N3 C13 C14 89.7(3) . . . . ? 
C17 N3 C13 C14 -53.8(3) . . . . ? 
N3 C13 C14 C15 55.3(3) . . . . ? 
C13 C14 C15 C16 -54.8(3) . . . . ? 
C14 C15 C16 C17 52.9(3) . . . . ? 
C9 N3 C17 C16 -90.1(3) . . . . ? 
C13 N3 C17 C16 53.3(3) . . . . ? 
C15 C16 C17 N3 -53.1(3) . . . . ? 
C1 C2 C19 C24 -110.8(3) . . . . ? 
C3 C2 C19 C24 66.3(3) . . . . ? 
C1 C2 C19 C20 67.5(3) . . . . ? 
C3 C2 C19 C20 -115.3(3) . . . . ? 
C24 C19 C20 C21 -0.4(4) . . . . ? 
C2 C19 C20 C21 -178.8(2) . . . . ? 
C19 C20 C21 C22 2.2(4) . . . . ? 
C20 C21 C22 C23 -1.7(4) . . . . ? 
C20 C21 C22 N4 178.7(2) . . . . ? 
C36 N4 C22 C21 132.4(3) . . . . ? 
C25 N4 C22 C21 -43.9(4) . . . . ? 
C36 N4 C22 C23 -47.2(4) . . . . ? 
C25 N4 C22 C23 136.5(3) . . . . ? 
C21 C22 C23 C24 -0.6(4) . . . . ? 
N4 C22 C23 C24 179.1(2) . . . . ? 
C22 C23 C24 C19 2.4(4) . . . . ? 
C20 C19 C24 C23 -1.9(4) . . . . ? 
C2 C19 C24 C23 176.5(2) . . . . ? 
C36 N4 C25 C26 177.6(3) . . . . ? 
C22 N4 C25 C26 -5.5(5) . . . . ? 
C36 N4 C25 C30 0.7(3) . . . . ? 
C22 N4 C25 C30 177.5(2) . . . . ? 
N4 C25 C26 C27 -177.7(3) . . . . ? 
C30 C25 C26 C27 -1.1(5) . . . . ? 
C25 C26 C27 C28 -0.1(6) . . . . ? 
C26 C27 C28 C29 1.0(7) . . . . ? 
C27 C28 C29 C30 -0.7(7) . . . . ? 
C28 C29 C30 C25 -0.4(6) . . . . ? 
C28 C29 C30 C31 178.8(4) . . . . ? 
C26 C25 C30 C29 1.3(4) . . . . ? 
N4 C25 C30 C29 178.6(3) . . . . ? 
C26 C25 C30 C31 -178.1(3) . . . . ? 
N4 C25 C30 C31 -0.8(3) . . . . ? 
C29 C30 C31 C32 3.0(6) . . . . ? 
C25 C30 C31 C32 -177.7(3) . . . . ? 
C29 C30 C31 C36 -178.6(4) . . . . ? 
C25 C30 C31 C36 0.7(3) . . . . ? 
C36 C31 C32 C33 -1.6(4) . . . . ? 
C30 C31 C32 C33 176.7(3) . . . . ? 
C31 C32 C33 C34 1.3(5) . . . . ? 
C32 C33 C34 C35 -0.3(5) . . . . ? 
C33 C34 C35 C36 -0.5(5) . . . . ? 
C34 C35 C36 N4 -176.9(3) . . . . ? 
C34 C35 C36 C31 0.2(4) . . . . ? 
C25 N4 C36 C35 177.1(3) . . . . ? 
C22 N4 C36 C35 0.3(4) . . . . ? 
C25 N4 C36 C31 -0.2(3) . . . . ? 
C22 N4 C36 C31 -177.1(2) . . . . ? 
C32 C31 C36 C35 0.8(4) . . . . ? 
C30 C31 C36 C35 -177.9(3) . . . . ? 
C32 C31 C36 N4 178.4(2) . . . . ? 
C30 C31 C36 N4 -0.3(3) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
C18 H18A N3  0.96 2.68 3.159(4) 111.7 . 
C18 H18A N3  0.96 2.68 3.159(4) 111.7 . 
  
_refine_diff_density_max    0.139 
_refine_diff_density_min   -0.138 
_refine_diff_density_rms    0.026 
  
_shelxl_version_number 2013-4 
  
  
  
