 
data_shelx
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C32 H26 N10 O2' 
_chemical_formula_weight          582.63

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    20.798(2)
_cell_length_b                    9.5020(5)
_cell_length_c                    14.4536(16)
_cell_angle_alpha                 90
_cell_angle_beta                  100.800(9)
_cell_angle_gamma                 90
_cell_volume                      2805.8(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.379          
_exptl_crystal_F_000              1216
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_absorpt_coefficient_mu     0.092
_shelx_estimated_absorpt_T_min    ? 
_shelx_estimated_absorpt_T_max    ? 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?                       
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             12331
_diffrn_reflns_av_unetI/netI      0.0931
_diffrn_reflns_av_R_equivalents   0.0710
_diffrn_reflns_limit_h_min        -24
_diffrn_reflns_limit_h_max        25
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          2.364
_diffrn_reflns_theta_max          26.141
_diffrn_reflns_theta_full         25.300
_diffrn_measured_fraction_theta_max   0.974
_diffrn_measured_fraction_theta_full  0.972
_diffrn_reflns_Laue_measured_fraction_max    0.974
_diffrn_reflns_Laue_measured_fraction_full   0.972
_diffrn_reflns_point_group_measured_fraction_max   0.974
_diffrn_reflns_point_group_measured_fraction_full  0.972
_reflns_number_total              5458
_reflns_number_gt                 2242
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 ?
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1010P)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_number_reflns          5458
_refine_ls_number_parameters      397
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1417
_refine_ls_R_factor_gt            0.0663
_refine_ls_wR_factor_ref          0.1796
_refine_ls_wR_factor_gt           0.1522
_refine_ls_goodness_of_fit_ref    0.815
_refine_ls_restrained_S_all       0.815
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.2494(3) 0.8544(4) 0.6526(3) 0.0629(12) Uani 1 1 d . . . . .
H1 H 0.2227 0.9052 0.6854 0.075 Uiso 1 1 calc R U . . .
C2 C 0.3142(3) 0.8836(4) 0.6717(3) 0.0699(13) Uani 1 1 d . . . . .
H2 H 0.3309 0.9523 0.7155 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3543(2) 0.8100(4) 0.6254(3) 0.0686(13) Uani 1 1 d . . . . .
H3 H 0.3991 0.8278 0.6381 0.082 Uiso 1 1 calc R U . . .
C4 C 0.3290(2) 0.7065(4) 0.5582(3) 0.0505(10) Uani 1 1 d . . . . .
C5 C 0.3667(2) 0.6298(4) 0.5053(3) 0.0630(11) Uani 1 1 d . . . . .
H5 H 0.4119 0.6428 0.5165 0.076 Uiso 1 1 calc R U . . .
C6 C 0.3398(2) 0.5388(4) 0.4395(3) 0.0661(13) Uani 1 1 d . . . . .
H6 H 0.3665 0.4916 0.4048 0.079 Uiso 1 1 calc R U . . .
C7 C 0.2701(2) 0.5110(4) 0.4202(2) 0.0485(10) Uani 1 1 d . . . . .
C8 C 0.2392(3) 0.4159(4) 0.3525(3) 0.0652(13) Uani 1 1 d . . . . .
H8 H 0.2637 0.3659 0.3159 0.078 Uiso 1 1 calc R U . . .
C9 C 0.1733(3) 0.3963(4) 0.3399(3) 0.0712(14) Uani 1 1 d . . . . .
H9 H 0.1522 0.3346 0.2942 0.085 Uiso 1 1 calc R U . . .
C10 C 0.1377(2) 0.4715(4) 0.3974(3) 0.0600(11) Uani 1 1 d . . . . .
H10 H 0.0928 0.4566 0.3894 0.072 Uiso 1 1 calc R U . . .
C11 C 0.23022(18) 0.5842(3) 0.4738(2) 0.0400(8) Uani 1 1 d . . . . .
C12 C 0.26011(18) 0.6856(3) 0.5431(2) 0.0410(8) Uani 1 1 d . . . . .
N1 N 0.22074(17) 0.7594(3) 0.5909(2) 0.0493(8) Uani 1 1 d . . . . .
N2 N 0.16494(16) 0.5621(3) 0.4622(2) 0.0468(7) Uani 1 1 d . . . . .
C13 C 0.3541(2) 0.2933(4) 0.6098(3) 0.0573(10) Uani 1 1 d . . . . .
H13 H 0.3986 0.3142 0.6211 0.069 Uiso 1 1 calc R U . . .
C14 C 0.3151(2) 0.3595(4) 0.6660(3) 0.0596(11) Uani 1 1 d . . . . .
H14 H 0.3334 0.4214 0.7135 0.071 Uiso 1 1 calc R U . . .
C15 C 0.2500(2) 0.3313(4) 0.6495(2) 0.0521(10) Uani 1 1 d . . . . .
H15 H 0.2232 0.3746 0.6859 0.063 Uiso 1 1 calc R U . . .
C16 C 0.22286(19) 0.2370(3) 0.5777(2) 0.0402(8) Uani 1 1 d . . . . .
C17 C 0.15530(19) 0.2063(3) 0.5547(2) 0.0508(9) Uani 1 1 d . . . . .
H17 H 0.1268 0.2510 0.5876 0.061 Uiso 1 1 calc R U . . .
C18 C 0.13114(18) 0.1142(4) 0.4864(2) 0.0510(9) Uani 1 1 d . . . . .
H18 H 0.0863 0.0971 0.4726 0.061 Uiso 1 1 calc R U . . .
C19 C 0.17323(19) 0.0426(3) 0.4350(2) 0.0413(8) Uani 1 1 d . . . . .
C20 C 0.1505(2) -0.0596(4) 0.3665(3) 0.0547(10) Uani 1 1 d . . . . .
H20 H 0.1062 -0.0821 0.3529 0.066 Uiso 1 1 calc R U . . .
C21 C 0.1929(2) -0.1255(4) 0.3202(3) 0.0560(10) Uani 1 1 d . . . . .
H21 H 0.1783 -0.1930 0.2745 0.067 Uiso 1 1 calc R U . . .
C22 C 0.2586(2) -0.0897(4) 0.3426(3) 0.0532(10) Uani 1 1 d . . . . .
H22 H 0.2873 -0.1359 0.3107 0.064 Uiso 1 1 calc R U . . .
C23 C 0.24079(18) 0.0714(3) 0.4537(2) 0.0385(8) Uani 1 1 d . . . . .
C24 C 0.26712(18) 0.1729(3) 0.5255(2) 0.0388(8) Uani 1 1 d . . . . .
N3 N 0.33175(17) 0.2025(3) 0.5414(2) 0.0469(8) Uani 1 1 d . . . . .
N4 N 0.28334(16) 0.0058(3) 0.4063(2) 0.0462(7) Uani 1 1 d . . . . .
C30 C 0.00430(16) 0.1991(3) 0.2567(2) 0.0408(10) Uani 1 1 d . . . . .
C31 C -0.05039(18) 0.0564(3) 0.3542(2) 0.0484(9) Uani 1 1 d . . . . .
H31 H -0.0622 -0.0325 0.3721 0.058 Uiso 1 1 calc R U . . .
C32 C -0.06978(19) 0.1707(3) 0.3958(2) 0.0504(9) Uani 1 1 d . . . . .
H32 H -0.0937 0.1633 0.4439 0.060 Uiso 1 1 calc R U . . .
C33 C -0.05204(16) 0.3041(3) 0.3631(2) 0.0402(8) Uani 1 1 d . . . . .
N5 N -0.01392(14) 0.0687(2) 0.28676(19) 0.0423(7) Uani 1 1 d . . . . .
H5A H -0.0016 -0.0062 0.2617 0.051 Uiso 1 1 calc R U . . .
N6 N -0.01519(14) 0.3143(2) 0.29686(19) 0.0419(7) Uani 1 1 d . . . . .
N7 N -0.07173(16) 0.4214(3) 0.3981(2) 0.0564(9) Uani 1 1 d . . . . .
H7A H -0.0608 0.5016 0.3783 0.068 Uiso 1 1 calc R U . . .
H7B H -0.0955 0.4176 0.4408 0.068 Uiso 1 1 calc R U . . .
O1 O 0.03890(14) 0.2017(2) 0.19501(17) 0.0602(8) Uani 1 1 d . . . . .
C40 C 0.49784(16) 0.4611(3) 0.2450(2) 0.0411(10) Uani 1 1 d . . . . .
C41 C 0.54756(18) 0.3217(3) 0.1424(2) 0.0516(10) Uani 1 1 d . . . . .
H41 H 0.5572 0.2325 0.1224 0.062 Uiso 1 1 calc R U . . .
C42 C 0.56830(19) 0.4362(3) 0.1011(2) 0.0507(9) Uani 1 1 d . . . . .
H42 H 0.5915 0.4284 0.0522 0.061 Uiso 1 1 calc R U . . .
C43 C 0.55274(16) 0.5696(3) 0.1364(2) 0.0405(8) Uani 1 1 d . . . . .
N8 N 0.51320(15) 0.3348(3) 0.2121(2) 0.0463(7) Uani 1 1 d . . . . .
H8A H 0.5005 0.2597 0.2367 0.056 Uiso 1 1 calc R U . . .
N9 N 0.51773(14) 0.5808(2) 0.20513(19) 0.0424(7) Uani 1 1 d . . . . .
N10 N 0.57291(16) 0.6880(3) 0.1019(2) 0.0538(8) Uani 1 1 d . . . . .
H10A H 0.5634 0.7680 0.1237 0.065 Uiso 1 1 calc R U . . .
H10B H 0.5955 0.6845 0.0577 0.065 Uiso 1 1 calc R U . . .
O2 O 0.46522(15) 0.4689(2) 0.30896(19) 0.0641(8) 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
C1 N1 1.329(5) . ?
C1 C2 1.353(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.357(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(5) . ?
C4 C12 1.422(6) . ?
C5 C6 1.329(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.449(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.397(6) . ?
C7 C11 1.419(4) . ?
C8 C9 1.362(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.408(6) . ?
C9 H9 0.9300 . ?
C10 N2 1.319(5) . ?
C10 H10 0.9300 . ?
C11 N2 1.353(5) . ?
C11 C12 1.443(4) . ?
C12 N1 1.361(4) . ?
C13 N3 1.329(5) . ?
C13 C14 1.400(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.407(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.413(5) . ?
C16 C24 1.432(4) . ?
C17 C18 1.344(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.423(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.403(5) . ?
C19 C23 1.407(5) . ?
C20 C21 1.357(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(6) . ?
C21 H21 0.9300 . ?
C22 N4 1.327(5) . ?
C22 H22 0.9300 . ?
C23 N4 1.367(4) . ?
C23 C24 1.447(4) . ?
C24 N3 1.350(5) . ?
C30 O1 1.246(3) . ?
C30 N6 1.337(4) . ?
C30 N5 1.389(4) . ?
C31 C32 1.339(4) . ?
C31 N5 1.348(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.426(4) . ?
C32 H32 0.9300 . ?
C33 N7 1.321(4) . ?
C33 N6 1.337(3) . ?
N5 H5A 0.8600 . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
C40 O2 1.248(3) . ?
C40 N8 1.351(4) . ?
C40 N9 1.373(4) . ?
C41 N8 1.346(4) . ?
C41 C42 1.349(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.426(4) . ?
C42 H42 0.9300 . ?
C43 N10 1.330(4) . ?
C43 N9 1.342(4) . ?
N8 H8A 0.8600 . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N1 C1 C2 125.5(4) . . ?
N1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
C1 C2 C3 118.3(4) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 124.3(4) . . ?
C5 C4 C12 119.7(4) . . ?
C3 C4 C12 116.0(4) . . ?
C6 C5 C4 121.7(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 121.9(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C11 117.5(4) . . ?
C8 C7 C6 124.4(4) . . ?
C11 C7 C6 118.1(4) . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 118.7(4) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
N2 C10 C9 123.1(4) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N2 C11 C7 122.1(3) . . ?
N2 C11 C12 118.8(3) . . ?
C7 C11 C12 119.1(3) . . ?
N1 C12 C4 122.3(3) . . ?
N1 C12 C11 118.3(3) . . ?
C4 C12 C11 119.4(3) . . ?
C1 N1 C12 117.0(4) . . ?
C10 N2 C11 118.5(3) . . ?
N3 C13 C14 124.3(4) . . ?
N3 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C15 C14 C13 118.5(4) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C17 123.3(3) . . ?
C15 C16 C24 116.8(4) . . ?
C17 C16 C24 119.8(3) . . ?
C18 C17 C16 121.8(3) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C23 117.6(3) . . ?
C20 C19 C18 122.7(4) . . ?
C23 C19 C18 119.8(3) . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 118.4(4) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
N4 C22 C21 124.6(3) . . ?
N4 C22 H22 117.7 . . ?
C21 C22 H22 117.7 . . ?
N4 C23 C19 122.1(3) . . ?
N4 C23 C24 118.0(3) . . ?
C19 C23 C24 119.9(3) . . ?
N3 C24 C16 122.6(3) . . ?
N3 C24 C23 119.5(3) . . ?
C16 C24 C23 117.9(3) . . ?
C13 N3 C24 117.4(3) . . ?
C22 N4 C23 117.1(3) . . ?
O1 C30 N6 123.8(3) . . ?
O1 C30 N5 118.1(3) . . ?
N6 C30 N5 118.1(2) . . ?
C32 C31 N5 120.8(3) . . ?
C32 C31 H31 119.6 . . ?
N5 C31 H31 119.6 . . ?
C31 C32 C33 116.9(3) . . ?
C31 C32 H32 121.5 . . ?
C33 C32 H32 121.5 . . ?
N7 C33 N6 118.3(3) . . ?
N7 C33 C32 120.3(3) . . ?
N6 C33 C32 121.4(3) . . ?
C31 N5 C30 121.8(2) . . ?
C31 N5 H5A 119.1 . . ?
C30 N5 H5A 119.1 . . ?
C33 N6 C30 120.9(2) . . ?
C33 N7 H7A 120.0 . . ?
C33 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
O2 C40 N8 120.7(3) . . ?
O2 C40 N9 120.7(3) . . ?
N8 C40 N9 118.6(2) . . ?
N8 C41 C42 121.0(3) . . ?
N8 C41 H41 119.5 . . ?
C42 C41 H41 119.5 . . ?
C41 C42 C43 116.5(3) . . ?
C41 C42 H42 121.8 . . ?
C43 C42 H42 121.8 . . ?
N10 C43 N9 117.6(3) . . ?
N10 C43 C42 120.6(3) . . ?
N9 C43 C42 121.7(3) . . ?
C41 N8 C40 122.6(3) . . ?
C41 N8 H8A 118.7 . . ?
C40 N8 H8A 118.7 . . ?
C43 N9 C40 119.5(2) . . ?
C43 N10 H10A 120.0 . . ?
C43 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
 
_refine_diff_density_max    0.422
_refine_diff_density_min   -0.252
_refine_diff_density_rms    0.073

_shelxl_version_number 2013-4



