 
data_A25170O_002_sq
 
_audit_creation_method            'SHELXL-2019/3'
_shelx_SHELXL_version_number      '2019/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C23 H20 N4'
_chemical_formula_sum
 'C23 H20 N4' 
_chemical_formula_weight          352.43

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       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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'
 
_cell_length_a                    10.9721(11)
_cell_length_b                    11.3455(11)
_cell_length_c                    17.3743(17)
_cell_angle_alpha                 86.726(3)
_cell_angle_beta                  87.154(3)
_cell_angle_gamma                 68.917(3)
_cell_volume                      2013.8(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     9918
_cell_measurement_theta_min       2.97
_cell_measurement_theta_max       28.00
 
_exptl_crystal_description        'needle'
_exptl_crystal_colour             'yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.162          
_exptl_crystal_F_000              744
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.122
_exptl_crystal_size_mid           0.025
_exptl_crystal_size_min           0.021
_exptl_absorpt_coefficient_mu     0.071
_shelx_estimated_absorpt_T_min    0.991
_shelx_estimated_absorpt_T_max    0.999
_exptl_absorpt_correction_type    MULTI-SCAN
_exptl_absorpt_correction_T_min   0.7155
_exptl_absorpt_correction_T_max   0.7404
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       173(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Ius 3.0 microfocus source'
_diffrn_measurement_device_type   'PHOTON II CPAD detector'
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             94994
_diffrn_reflns_av_unetI/netI      0.0365
_diffrn_reflns_av_R_equivalents   0.0793
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.577
_diffrn_reflns_theta_max          28.005
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              9690
_reflns_number_gt                 6938
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX5 software' 
_computing_cell_refinement        'Bruker APEX5 software' 
_computing_data_reduction         'Bruker APEX5 software' 
_computing_structure_solution     'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement   'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics     ORTEP
_computing_publication_material   CIFTAB
_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)+(0.0475P)²+1.1230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          9690
_refine_ls_number_parameters      499
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0881
_refine_ls_R_factor_gt            0.0584
_refine_ls_wR_factor_ref          0.1430
_refine_ls_wR_factor_gt           0.1260
_refine_ls_goodness_of_fit_ref    1.029
_refine_ls_restrained_S_all       1.029
_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 0.68475(15) 0.20432(16) 0.73999(9) 0.0266(3) Uani 1 1 d . . . . .
N2 N 0.71691(14) 0.08248(14) 0.73168(8) 0.0306(3) Uani 1 1 d . . . . .
C3 C 0.62774(17) 0.04452(17) 0.69516(10) 0.0326(4) Uani 1 1 d . . . . .
C4 C 0.6546(2) -0.0842(2) 0.68506(14) 0.0483(5) Uani 1 1 d . . . . .
H4 H 0.732534 -0.145585 0.704458 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5684(2) -0.1221(2) 0.64706(15) 0.0565(6) Uani 1 1 d . . . . .
H5 H 0.586891 -0.209583 0.640992 0.068 Uiso 1 1 calc R U . . .
C6 C 0.4546(2) -0.0332(2) 0.61750(14) 0.0532(6) Uani 1 1 d . . . . .
H6 H 0.396541 -0.060089 0.590613 0.064 Uiso 1 1 calc R U . . .
C7 C 0.42627(19) 0.0932(2) 0.62722(12) 0.0434(5) Uani 1 1 d . . . . .
H7 H 0.348469 0.153414 0.606919 0.052 Uiso 1 1 calc R U . . .
C8 C 0.51086(16) 0.13448(17) 0.66677(10) 0.0317(4) Uani 1 1 d . . . . .
N9 N 0.47884(13) 0.26180(14) 0.67690(8) 0.0312(3) Uani 1 1 d . . . . .
C10 C 0.56057(15) 0.29511(16) 0.71408(9) 0.0276(3) Uani 1 1 d . . . . .
N11 N 0.52955(14) 0.41855(14) 0.72985(9) 0.0326(3) Uani 1 1 d . . . . .
H11 H 0.446(2) 0.473(2) 0.7206(13) 0.049 Uiso 1 1 d . U . . .
C12 C 0.61171(16) 0.46368(16) 0.76752(10) 0.0316(4) Uani 1 1 d . . . . .
C13 C 0.57412(19) 0.59136(18) 0.78206(12) 0.0407(4) Uani 1 1 d . . . . .
H13 H 0.491637 0.648743 0.765870 0.049 Uiso 1 1 calc R U . . .
C14 C 0.6564(2) 0.63521(19) 0.82000(14) 0.0480(5) Uani 1 1 d . . . . .
H14 H 0.629869 0.722343 0.830364 0.058 Uiso 1 1 calc R U . . .
C15 C 0.7771(2) 0.5521(2) 0.84281(14) 0.0476(5) Uani 1 1 d . . . . .
H15 H 0.833305 0.582031 0.869195 0.057 Uiso 1 1 calc R U . . .
C16 C 0.81634(18) 0.42456(18) 0.82713(12) 0.0386(4) Uani 1 1 d . . . . .
H16 H 0.899925 0.368069 0.842234 0.046 Uiso 1 1 calc R U . . .
C17 C 0.73453(16) 0.37935(16) 0.78968(10) 0.0298(3) Uani 1 1 d . . . . .
N18 N 0.77056(13) 0.24993(13) 0.77352(8) 0.0286(3) Uani 1 1 d . . . . .
C19 C 0.90297(15) 0.16532(15) 0.78779(10) 0.0274(3) Uani 1 1 d . . . . .
C20 C 0.93772(18) 0.12048(17) 0.86271(10) 0.0332(4) Uani 1 1 d . . . . .
C21 C 1.06744(19) 0.04304(18) 0.87468(12) 0.0403(4) Uani 1 1 d . . . . .
H21 H 1.093113 0.011692 0.925513 0.048 Uiso 1 1 calc R U . . .
C22 C 1.15971(18) 0.01055(17) 0.81481(13) 0.0404(5) Uani 1 1 d . . . . .
C23 C 1.12167(17) 0.05894(17) 0.74098(12) 0.0368(4) Uani 1 1 d . . . . .
H23 H 1.184649 0.038325 0.699604 0.044 Uiso 1 1 calc R U . . .
C24 C 0.99363(17) 0.13687(17) 0.72600(10) 0.0312(4) Uani 1 1 d . . . . .
C25 C 0.8411(2) 0.1548(2) 0.93000(11) 0.0445(5) Uani 1 1 d . . . . .
H25A H 0.876276 0.189510 0.970231 0.067 Uiso 1 1 calc R U . . .
H25B H 0.825667 0.079050 0.950762 0.067 Uiso 1 1 calc R U . . .
H25C H 0.758565 0.218099 0.912730 0.067 Uiso 1 1 calc R U . . .
C26 C 1.2991(2) -0.0771(2) 0.82779(17) 0.0612(7) Uani 1 1 d . . . . .
H26A H 1.359313 -0.043985 0.798537 0.092 Uiso 1 1 calc R U . . .
H26B H 1.311083 -0.161372 0.810384 0.092 Uiso 1 1 calc R U . . .
H26C H 1.317013 -0.082833 0.882843 0.092 Uiso 1 1 calc R U . . .
C27 C 0.9558(2) 0.1852(2) 0.64512(11) 0.0469(5) Uani 1 1 d . . . . .
H27A H 1.034493 0.178063 0.613563 0.070 Uiso 1 1 calc R U . . .
H27B H 0.897695 0.274045 0.645715 0.070 Uiso 1 1 calc R U . . .
H27C H 0.910512 0.135119 0.623294 0.070 Uiso 1 1 calc R U . . .
C31 C 0.16639(16) 0.67854(15) 0.74680(9) 0.0266(3) Uani 1 1 d . . . . .
N32 N 0.27176(13) 0.62673(13) 0.70353(8) 0.0292(3) Uani 1 1 d . . . . .
C33 C 0.27924(17) 0.68525(17) 0.63179(10) 0.0313(4) Uani 1 1 d . . . . .
C34 C 0.39063(19) 0.6363(2) 0.58345(11) 0.0426(5) Uani 1 1 d . . . . .
H34 H 0.460392 0.562187 0.599532 0.051 Uiso 1 1 calc R U . . .
C35 C 0.3996(2) 0.6950(2) 0.51277(11) 0.0448(5) Uani 1 1 d . . . . .
H35 H 0.475377 0.661496 0.480437 0.054 Uiso 1 1 calc R U . . .
C36 C 0.2970(2) 0.8039(2) 0.48874(11) 0.0422(5) Uani 1 1 d . . . . .
H36 H 0.303564 0.844285 0.440104 0.051 Uiso 1 1 calc R U . . .
C37 C 0.18693(18) 0.85288(19) 0.53478(10) 0.0372(4) Uani 1 1 d . . . . .
H37 H 0.117674 0.926669 0.517709 0.045 Uiso 1 1 calc R U . . .
C38 C 0.17581(16) 0.79474(16) 0.60705(10) 0.0298(3) Uani 1 1 d . . . . .
N39 N 0.06517(14) 0.84722(14) 0.65323(8) 0.0319(3) Uani 1 1 d . . . . .
C40 C 0.06165(15) 0.79260(15) 0.72098(10) 0.0273(3) Uani 1 1 d . . . . .
N41 N -0.04339(14) 0.84360(14) 0.76965(9) 0.0315(3) Uani 1 1 d . . . . .
H41 H -0.110(2) 0.923(2) 0.7551(13) 0.047 Uiso 1 1 d . U . . .
C42 C -0.05414(16) 0.79325(15) 0.84336(10) 0.0274(3) Uani 1 1 d . . . . .
C43 C -0.16296(17) 0.85177(17) 0.89084(11) 0.0339(4) Uani 1 1 d . . . . .
H43 H -0.230389 0.926031 0.872554 0.041 Uiso 1 1 calc R U . . .
C44 C -0.17335(19) 0.80226(18) 0.96453(11) 0.0382(4) Uani 1 1 d . . . . .
H44 H -0.247509 0.842822 0.996773 0.046 Uiso 1 1 calc R U . . .
C45 C -0.07556(19) 0.69356(18) 0.99121(11) 0.0368(4) Uani 1 1 d . . . . .
H45 H -0.082063 0.659913 1.041938 0.044 Uiso 1 1 calc R U . . .
C46 C 0.03229(17) 0.63378(16) 0.94342(10) 0.0326(4) Uani 1 1 d . . . . .
H46 H 0.098602 0.558656 0.961701 0.039 Uiso 1 1 calc R U . . .
C47 C 0.04431(16) 0.68239(15) 0.86943(10) 0.0273(3) Uani 1 1 d . . . . .
N48 N 0.15226(13) 0.62364(13) 0.81926(8) 0.0273(3) Uani 1 1 d . . . . .
C49 C 0.24146(15) 0.49790(15) 0.84002(9) 0.0261(3) Uani 1 1 d . . . . .
C50 C 0.33416(17) 0.48173(17) 0.89594(10) 0.0313(4) Uani 1 1 d . . . . .
C51 C 0.41373(17) 0.35827(18) 0.91709(10) 0.0348(4) Uani 1 1 d . . . . .
H51 H 0.477108 0.345491 0.955080 0.042 Uiso 1 1 calc R U . . .
C52 C 0.40320(17) 0.25408(16) 0.88450(11) 0.0333(4) Uani 1 1 d . . . . .
C53 C 0.30938(17) 0.27376(16) 0.82933(10) 0.0319(4) Uani 1 1 d . . . . .
H53 H 0.300539 0.202749 0.807150 0.038 Uiso 1 1 calc R U . . .
C54 C 0.22829(16) 0.39452(16) 0.80582(10) 0.0284(3) Uani 1 1 d . . . . .
C55 C 0.3489(2) 0.59091(19) 0.93477(12) 0.0422(4) Uani 1 1 d . . . . .
H55A H 0.438129 0.589847 0.925646 0.063 Uiso 1 1 calc R U . . .
H55B H 0.331435 0.583430 0.990357 0.063 Uiso 1 1 calc R U . . .
H55C H 0.286685 0.670520 0.913607 0.063 Uiso 1 1 calc R U . . .
C56 C 0.4924(2) 0.12153(19) 0.90771(13) 0.0472(5) Uani 1 1 d . . . . .
H56A H 0.440451 0.067572 0.917960 0.071 Uiso 1 1 calc R U . . .
H56B H 0.538017 0.123952 0.954356 0.071 Uiso 1 1 calc R U . . .
H56C H 0.556584 0.087279 0.865834 0.071 Uiso 1 1 calc R U . . .
C57 C 0.13321(18) 0.41161(18) 0.74302(11) 0.0375(4) Uani 1 1 d . . . . .
H57A H 0.115799 0.333337 0.739032 0.056 Uiso 1 1 calc R U . . .
H57B H 0.170467 0.431858 0.693840 0.056 Uiso 1 1 calc R U . . .
H57C H 0.051378 0.480793 0.755244 0.056 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
C1 N2 1.313(2) . ?
C1 N18 1.390(2) . ?
C1 C10 1.455(2) . ?
N2 C3 1.393(2) . ?
C3 C4 1.402(3) . ?
C3 C8 1.412(2) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.373(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(3) . ?
C7 H7 0.9500 . ?
C8 N9 1.378(2) . ?
N9 C10 1.301(2) . ?
C10 N11 1.358(2) . ?
N11 C12 1.390(2) . ?
N11 H11 0.92(2) . ?
C12 C13 1.391(3) . ?
C12 C17 1.401(2) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 N18 1.418(2) . ?
N18 C19 1.449(2) . ?
C19 C20 1.390(2) . ?
C19 C24 1.396(2) . ?
C20 C21 1.396(3) . ?
C20 C25 1.508(3) . ?
C21 C22 1.383(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 C26 1.514(3) . ?
C23 C24 1.393(2) . ?
C23 H23 0.9500 . ?
C24 C27 1.501(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C31 N32 1.313(2) . ?
C31 N48 1.399(2) . ?
C31 C40 1.453(2) . ?
N32 C33 1.391(2) . ?
C33 C34 1.404(3) . ?
C33 C38 1.410(2) . ?
C34 C35 1.380(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.398(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.370(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.405(2) . ?
C37 H37 0.9500 . ?
C38 N39 1.382(2) . ?
N39 C40 1.304(2) . ?
C40 N41 1.363(2) . ?
N41 C42 1.389(2) . ?
N41 H41 0.96(2) . ?
C42 C43 1.393(2) . ?
C42 C47 1.400(2) . ?
C43 C44 1.385(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.385(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.392(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.389(2) . ?
C46 H46 0.9500 . ?
C47 N48 1.415(2) . ?
N48 C49 1.447(2) . ?
C49 C50 1.398(2) . ?
C49 C54 1.400(2) . ?
C50 C51 1.397(2) . ?
C50 C55 1.505(3) . ?
C51 C52 1.383(3) . ?
C51 H51 0.9500 . ?
C52 C53 1.392(3) . ?
C52 C56 1.514(2) . ?
C53 C54 1.389(2) . ?
C53 H53 0.9500 . ?
C54 C57 1.503(2) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
 
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 C1 N18 120.14(15) . . ?
N2 C1 C10 121.66(15) . . ?
N18 C1 C10 118.20(15) . . ?
C1 N2 C3 116.74(15) . . ?
N2 C3 C4 119.99(17) . . ?
N2 C3 C8 120.80(16) . . ?
C4 C3 C8 119.21(17) . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.00(19) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.74(19) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N9 C8 C7 119.52(17) . . ?
N9 C8 C3 121.26(16) . . ?
C7 C8 C3 119.22(18) . . ?
C10 N9 C8 117.09(15) . . ?
N9 C10 N11 119.32(15) . . ?
N9 C10 C1 122.28(16) . . ?
N11 C10 C1 118.39(15) . . ?
C10 N11 C12 123.53(15) . . ?
C10 N11 H11 117.9(14) . . ?
C12 N11 H11 118.1(14) . . ?
N11 C12 C13 120.76(16) . . ?
N11 C12 C17 119.25(16) . . ?
C13 C12 C17 119.98(17) . . ?
C14 C13 C12 120.30(18) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.94(18) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.05(19) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.56(18) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 119.16(16) . . ?
C16 C17 N18 122.14(16) . . ?
C12 C17 N18 118.70(15) . . ?
C1 N18 C17 121.64(14) . . ?
C1 N18 C19 119.44(14) . . ?
C17 N18 C19 118.80(13) . . ?
C20 C19 C24 122.03(16) . . ?
C20 C19 N18 119.36(15) . . ?
C24 C19 N18 118.53(15) . . ?
C19 C20 C21 117.76(17) . . ?
C19 C20 C25 122.15(17) . . ?
C21 C20 C25 120.08(17) . . ?
C22 C21 C20 122.02(18) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C21 C22 C23 118.49(17) . . ?
C21 C22 C26 121.7(2) . . ?
C23 C22 C26 119.8(2) . . ?
C22 C23 C24 121.73(18) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C19 117.95(17) . . ?
C23 C24 C27 120.11(17) . . ?
C19 C24 C27 121.92(16) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N32 C31 N48 120.19(14) . . ?
N32 C31 C40 121.41(15) . . ?
N48 C31 C40 118.40(14) . . ?
C31 N32 C33 117.36(14) . . ?
N32 C33 C34 120.21(16) . . ?
N32 C33 C38 120.54(15) . . ?
C34 C33 C38 119.25(16) . . ?
C35 C34 C33 120.51(18) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 119.96(18) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C37 C36 C35 120.53(17) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 120.48(18) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
N39 C38 C37 119.52(16) . . ?
N39 C38 C33 121.20(15) . . ?
C37 C38 C33 119.27(16) . . ?
C40 N39 C38 117.21(15) . . ?
N39 C40 N41 119.32(15) . . ?
N39 C40 C31 122.24(15) . . ?
N41 C40 C31 118.44(15) . . ?
C40 N41 C42 123.22(14) . . ?
C40 N41 H41 119.1(13) . . ?
C42 N41 H41 117.3(13) . . ?
N41 C42 C43 120.28(15) . . ?
N41 C42 C47 119.63(15) . . ?
C43 C42 C47 120.08(16) . . ?
C44 C43 C42 120.36(17) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 119.97(17) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C44 C45 C46 119.78(17) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C47 C46 C45 120.95(17) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C46 C47 C42 118.85(15) . . ?
C46 C47 N48 122.38(15) . . ?
C42 C47 N48 118.77(15) . . ?
C31 N48 C47 121.35(13) . . ?
C31 N48 C49 119.40(13) . . ?
C47 N48 C49 118.89(13) . . ?
C50 C49 C54 121.56(15) . . ?
C50 C49 N48 119.72(15) . . ?
C54 C49 N48 118.66(14) . . ?
C51 C50 C49 117.78(16) . . ?
C51 C50 C55 119.45(16) . . ?
C49 C50 C55 122.75(16) . . ?
C52 C51 C50 122.13(17) . . ?
C52 C51 H51 118.9 . . ?
C50 C51 H51 118.9 . . ?
C51 C52 C53 118.49(16) . . ?
C51 C52 C56 120.85(18) . . ?
C53 C52 C56 120.66(18) . . ?
C54 C53 C52 121.76(17) . . ?
C54 C53 H53 119.1 . . ?
C52 C53 H53 119.1 . . ?
C53 C54 C49 118.28(16) . . ?
C53 C54 C57 119.95(16) . . ?
C49 C54 C57 121.73(15) . . ?
C50 C55 H55A 109.5 . . ?
C50 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C50 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C52 C56 H56A 109.5 . . ?
C52 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C52 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C54 C57 H57A 109.5 . . ?
C54 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C54 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 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
N18 C1 N2 C3 -177.84(15) . . . . ?
C10 C1 N2 C3 1.5(2) . . . . ?
C1 N2 C3 C4 -179.23(17) . . . . ?
C1 N2 C3 C8 1.9(2) . . . . ?
N2 C3 C4 C5 -178.2(2) . . . . ?
C8 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 0.0(4) . . . . ?
C6 C7 C8 N9 -178.82(19) . . . . ?
C6 C7 C8 C3 1.5(3) . . . . ?
N2 C3 C8 N9 -2.6(3) . . . . ?
C4 C3 C8 N9 178.49(17) . . . . ?
N2 C3 C8 C7 177.10(17) . . . . ?
C4 C3 C8 C7 -1.8(3) . . . . ?
C7 C8 N9 C10 179.91(16) . . . . ?
C3 C8 N9 C10 -0.4(2) . . . . ?
C8 N9 C10 N11 -175.85(15) . . . . ?
C8 N9 C10 C1 3.8(2) . . . . ?
N2 C1 C10 N9 -4.7(2) . . . . ?
N18 C1 C10 N9 174.69(15) . . . . ?
N2 C1 C10 N11 175.03(15) . . . . ?
N18 C1 C10 N11 -5.6(2) . . . . ?
N9 C10 N11 C12 -178.38(16) . . . . ?
C1 C10 N11 C12 1.9(2) . . . . ?
C10 N11 C12 C13 -179.92(17) . . . . ?
C10 N11 C12 C17 1.2(3) . . . . ?
N11 C12 C13 C14 179.63(19) . . . . ?
C17 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C12 0.2(3) . . . . ?
C15 C16 C17 N18 -179.28(18) . . . . ?
N11 C12 C17 C16 179.91(17) . . . . ?
C13 C12 C17 C16 1.0(3) . . . . ?
N11 C12 C17 N18 -0.6(2) . . . . ?
C13 C12 C17 N18 -179.48(16) . . . . ?
N2 C1 N18 C17 -174.27(15) . . . . ?
C10 C1 N18 C17 6.4(2) . . . . ?
N2 C1 N18 C19 9.9(2) . . . . ?
C10 C1 N18 C19 -169.51(14) . . . . ?
C16 C17 N18 C1 176.18(16) . . . . ?
C12 C17 N18 C1 -3.3(2) . . . . ?
C16 C17 N18 C19 -7.9(2) . . . . ?
C12 C17 N18 C19 172.60(15) . . . . ?
C1 N18 C19 C20 -105.03(18) . . . . ?
C17 N18 C19 C20 79.0(2) . . . . ?
C1 N18 C19 C24 78.4(2) . . . . ?
C17 N18 C19 C24 -97.63(19) . . . . ?
C24 C19 C20 C21 -1.1(3) . . . . ?
N18 C19 C20 C21 -177.60(16) . . . . ?
C24 C19 C20 C25 177.80(17) . . . . ?
N18 C19 C20 C25 1.3(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C25 C20 C21 C22 -179.14(18) . . . . ?
C20 C21 C22 C23 1.2(3) . . . . ?
C20 C21 C22 C26 -177.84(19) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
C26 C22 C23 C24 178.07(18) . . . . ?
C22 C23 C24 C19 -0.2(3) . . . . ?
C22 C23 C24 C27 -178.81(18) . . . . ?
C20 C19 C24 C23 1.3(3) . . . . ?
N18 C19 C24 C23 177.82(15) . . . . ?
C20 C19 C24 C27 179.88(17) . . . . ?
N18 C19 C24 C27 -3.6(3) . . . . ?
N48 C31 N32 C33 179.38(15) . . . . ?
C40 C31 N32 C33 -0.1(2) . . . . ?
C31 N32 C33 C34 178.53(17) . . . . ?
C31 N32 C33 C38 -1.0(2) . . . . ?
N32 C33 C34 C35 -178.97(18) . . . . ?
C38 C33 C34 C35 0.5(3) . . . . ?
C33 C34 C35 C36 -0.2(3) . . . . ?
C34 C35 C36 C37 -0.2(3) . . . . ?
C35 C36 C37 C38 0.3(3) . . . . ?
C36 C37 C38 N39 178.65(18) . . . . ?
C36 C37 C38 C33 0.0(3) . . . . ?
N32 C33 C38 N39 0.4(3) . . . . ?
C34 C33 C38 N39 -179.05(17) . . . . ?
N32 C33 C38 C37 179.07(16) . . . . ?
C34 C33 C38 C37 -0.4(3) . . . . ?
C37 C38 N39 C40 -177.42(16) . . . . ?
C33 C38 N39 C40 1.2(2) . . . . ?
C38 N39 C40 N41 177.66(15) . . . . ?
C38 N39 C40 C31 -2.3(2) . . . . ?
N32 C31 C40 N39 1.8(3) . . . . ?
N48 C31 C40 N39 -177.65(15) . . . . ?
N32 C31 C40 N41 -178.12(15) . . . . ?
N48 C31 C40 N41 2.4(2) . . . . ?
N39 C40 N41 C42 -178.67(16) . . . . ?
C31 C40 N41 C42 1.3(2) . . . . ?
C40 N41 C42 C43 178.56(16) . . . . ?
C40 N41 C42 C47 -2.2(2) . . . . ?
N41 C42 C43 C44 -179.50(17) . . . . ?
C47 C42 C43 C44 1.3(3) . . . . ?
C42 C43 C44 C45 -0.4(3) . . . . ?
C43 C44 C45 C46 -0.6(3) . . . . ?
C44 C45 C46 C47 0.8(3) . . . . ?
C45 C46 C47 C42 0.1(3) . . . . ?
C45 C46 C47 N48 -179.66(16) . . . . ?
N41 C42 C47 C46 179.66(15) . . . . ?
C43 C42 C47 C46 -1.1(2) . . . . ?
N41 C42 C47 N48 -0.6(2) . . . . ?
C43 C42 C47 N48 178.65(15) . . . . ?
N32 C31 N48 C47 175.31(15) . . . . ?
C40 C31 N48 C47 -5.2(2) . . . . ?
N32 C31 N48 C49 -11.7(2) . . . . ?
C40 C31 N48 C49 167.80(14) . . . . ?
C46 C47 N48 C31 -175.94(15) . . . . ?
C42 C47 N48 C31 4.3(2) . . . . ?
C46 C47 N48 C49 11.0(2) . . . . ?
C42 C47 N48 C49 -168.71(14) . . . . ?
C31 N48 C49 C50 109.51(18) . . . . ?
C47 N48 C49 C50 -77.3(2) . . . . ?
C31 N48 C49 C54 -73.5(2) . . . . ?
C47 N48 C49 C54 99.71(18) . . . . ?
C54 C49 C50 C51 -0.2(2) . . . . ?
N48 C49 C50 C51 176.73(15) . . . . ?
C54 C49 C50 C55 -178.83(17) . . . . ?
N48 C49 C50 C55 -1.9(3) . . . . ?
C49 C50 C51 C52 0.2(3) . . . . ?
C55 C50 C51 C52 178.82(17) . . . . ?
C50 C51 C52 C53 -0.5(3) . . . . ?
C50 C51 C52 C56 178.97(17) . . . . ?
C51 C52 C53 C54 0.9(3) . . . . ?
C56 C52 C53 C54 -178.56(16) . . . . ?
C52 C53 C54 C49 -1.0(2) . . . . ?
C52 C53 C54 C57 176.73(16) . . . . ?
C50 C49 C54 C53 0.6(2) . . . . ?
N48 C49 C54 C53 -176.37(14) . . . . ?
C50 C49 C54 C57 -177.04(16) . . . . ?
N48 C49 C54 C57 6.0(2) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag
N11 H11 N32  0.92(2) 2.10(2) 2.998(2) 168(2) . yes
N41 H41 N2  0.96(2) 2.14(2) 3.088(2) 168.6(19) 1_465 yes
 
_refine_diff_density_max    0.292
_refine_diff_density_min   -0.258
_refine_diff_density_rms    0.043




