data_mo_191213_lpy_cz_cz_0m
_audit_creation_date               2020-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C46 H28 N4'
_chemical_formula_sum              'C46 H28 N4'
_chemical_formula_weight           636.72
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     10.8827(4)
_cell_length_b                     25.7626(9)
_cell_length_c                     13.4803(5)
_cell_angle_alpha                  90
_cell_angle_beta                   98.6170(10)
_cell_angle_gamma                  90
_cell_volume                       3736.8(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9971
_cell_measurement_temperature      180(2)
_cell_measurement_theta_max        24.93
_cell_measurement_theta_min        2.25
_shelx_estimated_absorpt_T_max     0.993
_shelx_estimated_absorpt_T_min     0.981
_exptl_absorpt_coefficient_mu      0.067
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6691
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1335 before and 0.0600 after correction.
The Ratio of minimum to maximum transmission is 0.8974.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'colourless'
_exptl_crystal_density_diffrn      1.132
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'Block'
_exptl_crystal_F_000               1328
_exptl_crystal_size_max            0.29
_exptl_crystal_size_mid            0.21
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0725
_diffrn_reflns_av_unetI/netI       0.0615
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.995
_diffrn_reflns_limit_h_max         14
_diffrn_reflns_limit_h_min         -12
_diffrn_reflns_limit_k_max         33
_diffrn_reflns_limit_k_min         -33
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -16
_diffrn_reflns_number              53192
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.995
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.578
_diffrn_reflns_theta_min           2.199
_diffrn_ambient_temperature        179.99
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  5216
_reflns_number_total               8611
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         ?
_computing_data_collection         ?
_computing_data_reduction          ?
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max           0.183
_refine_diff_density_min           -0.235
_refine_diff_density_rms           0.045
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       451
_refine_ls_number_reflns           8611
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0926
_refine_ls_R_factor_gt             0.0496
_refine_ls_restrained_S_all        1.038
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0640P)²+0.2207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1171
_refine_ls_wR_factor_ref           0.1327
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C31(H31)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28),
  C34(H34), C35(H35), C36(H36), C37(H37), C40(H40), C41(H41), C43(H43),
 C44(H44), C45(H45), C46(H46)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
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 0.18266(11) 0.71197(5) 0.24338(9) 0.0335(3) Uani 1 1 d . . . . .
 N2 N 0.89012(11) 0.60631(5) 0.61835(9) 0.0333(3) Uani 1 1 d . . . . .
 N3 N 0.45974(11) 0.48439(5) 0.22055(9) 0.0312(3) Uani 1 1 d . . . . .
 N4 N 0.66554(12) 0.53344(5) 0.14835(9) 0.0344(3) Uani 1 1 d . . . . .
 C1 C -0.0457(2) 0.73831(9) 0.45589(19) 0.0752(7) Uani 1 1 d . . . . .
 H1 H -0.1010 0.7453 0.5025 0.090 Uiso 1 1 calc R . . . .
 C2 C -0.07079(19) 0.75851(9) 0.36074(19) 0.0670(6) Uani 1 1 d . . . . .
 H2 H -0.1425 0.7793 0.3418 0.080 Uiso 1 1 calc R . . . .
 C3 C 0.01015(15) 0.74811(7) 0.29214(14) 0.0430(4) Uani 1 1 d . . . . .
 C4 C 0.11349(15) 0.71635(6) 0.32263(12) 0.0358(4) Uani 1 1 d . . . . .
 C5 C 0.29889(14) 0.68676(6) 0.24757(11) 0.0302(4) Uani 1 1 d . . . . .
 C6 C 0.31248(14) 0.63623(6) 0.28455(11) 0.0296(3) Uani 1 1 d . . . . .
 H6 H 0.2438 0.6185 0.3048 0.035 Uiso 1 1 calc R . . . .
 C7 C 0.42678(13) 0.61236(6) 0.29141(10) 0.0273(3) Uani 1 1 d . . . . .
 C8 C 0.45918(13) 0.55923(6) 0.33662(11) 0.0273(3) Uani 1 1 d . . . . .
 H8 H 0.3879 0.5421 0.3624 0.033 Uiso 1 1 calc R . . . .
 C9 C 0.57080(13) 0.56806(6) 0.41769(11) 0.0273(3) Uani 1 1 d . . . . .
 C10 C 0.57702(14) 0.55713(6) 0.51850(11) 0.0292(3) Uani 1 1 d . . . . .
 H10 H 0.5082 0.5416 0.5428 0.035 Uiso 1 1 calc R . . . .
 C11 C 0.68394(14) 0.56882(6) 0.58419(11) 0.0314(4) Uani 1 1 d . . . . .
 H11 H 0.6892 0.5606 0.6534 0.038 Uiso 1 1 calc R . . . .
 C12 C 0.78346(14) 0.59260(6) 0.54890(11) 0.0304(3) Uani 1 1 d . . . . .
 C13 C 0.88727(15) 0.63130(6) 0.70991(11) 0.0322(4) Uani 1 1 d . . . . .
 C14 C 0.78612(16) 0.65089(6) 0.74993(12) 0.0376(4) Uani 1 1 d . . . . .
 H14 H 0.7042 0.6487 0.7141 0.045 Uiso 1 1 calc R . . . .
 C15 C 0.80945(17) 0.67363(6) 0.84383(13) 0.0432(4) Uani 1 1 d . . . . .
 H15 H 0.7419 0.6870 0.8732 0.052 Uiso 1 1 calc R . . . .
 C16 C 0.92880(18) 0.67739(7) 0.89622(13) 0.0457(4) Uani 1 1 d . . . . .
 H16 H 0.9417 0.6932 0.9606 0.055 Uiso 1 1 calc R . . . .
 C17 C -0.0156(2) 0.80757(8) 0.03295(18) 0.0683(7) Uani 1 1 d . . . . .
 H17 H -0.0616 0.8313 -0.0122 0.082 Uiso 1 1 calc R . . . .
 C18 C -0.05246(19) 0.79807(8) 0.12375(18) 0.0624(6) Uani 1 1 d . . . . .
 H18 H -0.1253 0.8140 0.1407 0.075 Uiso 1 1 calc R . . . .
 C19 C 0.01801(15) 0.76477(7) 0.19123(14) 0.0439(4) Uani 1 1 d . . . . .
 C20 C 0.12445(14) 0.74182(6) 0.16336(12) 0.0355(4) Uani 1 1 d . . . . .
 C21 C 0.15854(17) 0.74956(7) 0.06978(13) 0.0459(4) Uani 1 1 d . . . . .
 H21 H 0.2283 0.7323 0.0504 0.055 Uiso 1 1 calc R . . . .
 C22 C 0.0876(2) 0.78331(8) 0.00563(15) 0.0600(6) Uani 1 1 d . . . . .
 H22 H 0.1101 0.7900 -0.0586 0.072 Uiso 1 1 calc R . . . .
 C23 C 0.50717(13) 0.52849(6) 0.25475(10) 0.0280(3) Uani 1 1 d . . . . .
 C24 C 0.51655(14) 0.46259(6) 0.14527(11) 0.0329(4) Uani 1 1 d . . . . .
 C25 C 0.47183(17) 0.41481(7) 0.10367(12) 0.0422(4) Uani 1 1 d . . . . .
 H25 H 0.4034 0.3984 0.1270 0.051 Uiso 1 1 calc R . . . .
 C26 C 0.52665(18) 0.39203(7) 0.02992(13) 0.0502(5) Uani 1 1 d . . . . .
 H26 H 0.4958 0.3599 0.0019 0.060 Uiso 1 1 calc R . . . .
 C27 C 0.62744(19) 0.41561(8) -0.00437(13) 0.0505(5) Uani 1 1 d . . . . .
 H27 H 0.6650 0.3992 -0.0554 0.061 Uiso 1 1 calc R . . . .
 C28 C 0.67330(17) 0.46219(7) 0.03448(12) 0.0450(4) Uani 1 1 d . . . . .
 H28 H 0.7420 0.4780 0.0104 0.054 Uiso 1 1 calc R . . . .
 C29 C 0.61790(15) 0.48640(6) 0.11019(11) 0.0345(4) Uani 1 1 d . . . . .
 C30 C 0.60963(14) 0.55309(6) 0.21826(11) 0.0292(3) Uani 1 1 d . . . . .
 C31 C 0.64546(13) 0.60436(6) 0.27042(11) 0.0297(4) Uani 1 1 d . . . . .
 H31 H 0.7168 0.6219 0.2453 0.036 Uiso 1 1 calc R . . . .
 C32 C 0.67100(14) 0.59178(6) 0.38236(11) 0.0284(3) Uani 1 1 d . . . . .
 C33 C 1.01302(14) 0.59298(6) 0.61197(12) 0.0330(4) Uani 1 1 d . . . . .
 C34 C 1.06092(15) 0.56629(6) 0.53719(12) 0.0390(4) Uani 1 1 d . . . . .
 H34 H 1.0088 0.5548 0.4784 0.047 Uiso 1 1 calc R . . . .
 C35 C 1.18767(17) 0.55702(7) 0.55136(13) 0.0467(5) Uani 1 1 d . . . . .
 H35 H 1.2229 0.5384 0.5017 0.056 Uiso 1 1 calc R . . . .
 C36 C 1.26456(16) 0.57434(7) 0.63688(14) 0.0489(5) Uani 1 1 d . . . . .
 H36 H 1.3514 0.5680 0.6440 0.059 Uiso 1 1 calc R . . . .
 C37 C 1.21613(15) 0.60055(7) 0.71109(13) 0.0417(4) Uani 1 1 d . . . . .
 H37 H 1.2688 0.6119 0.7697 0.050 Uiso 1 1 calc R . . . .
 C38 C 1.08940(14) 0.61025(6) 0.69915(11) 0.0331(4) Uani 1 1 d . . . . .
 C39 C 1.00896(15) 0.63477(6) 0.76183(11) 0.0335(4) Uani 1 1 d . . . . .
 C40 C 1.02917(17) 0.65842(7) 0.85581(12) 0.0424(4) Uani 1 1 d . . . . .
 H40 H 1.1110 0.6615 0.8916 0.051 Uiso 1 1 calc R . . . .
 C41 C 0.77760(14) 0.60437(6) 0.44768(11) 0.0304(4) Uani 1 1 d . . . . .
 H41 H 0.8456 0.6208 0.4237 0.036 Uiso 1 1 calc R . . . .
 C42 C 0.52718(13) 0.63719(6) 0.25721(10) 0.0277(3) Uani 1 1 d . . . . .
 C43 C 0.51271(14) 0.68697(6) 0.21957(11) 0.0313(4) Uani 1 1 d . . . . .
 H43 H 0.5801 0.7040 0.1958 0.038 Uiso 1 1 calc R . . . .
 C44 C 0.39942(14) 0.71220(6) 0.21657(11) 0.0315(4) Uani 1 1 d . . . . .
 H44 H 0.3905 0.7470 0.1932 0.038 Uiso 1 1 calc R . . . .
 C45 C 0.0576(2) 0.70819(8) 0.48519(15) 0.0598(6) Uani 1 1 d . . . . .
 H45 H 0.0731 0.6953 0.5520 0.072 Uiso 1 1 calc R . . . .
 C46 C 0.13893(17) 0.69629(7) 0.41955(13) 0.0442(4) Uani 1 1 d . . . . .
 H46 H 0.2099 0.6752 0.4396 0.053 Uiso 1 1 calc R . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 N1 C4 1.4007(19) . ?
 N1 C5 1.4155(19) . ?
 N1 C20 1.3971(19) . ?
 N2 C12 1.4223(18) . ?
 N2 C13 1.3965(19) . ?
 N2 C33 1.396(2) . ?
 N3 C23 1.3034(19) . ?
 N3 C24 1.3839(19) . ?
 N4 C29 1.386(2) . ?
 N4 C30 1.2986(19) . ?
 C1 H1 0.9500 . ?
 C1 C2 1.373(3) . ?
 C1 C45 1.374(3) . ?
 C2 H2 0.9500 . ?
 C2 C3 1.395(3) . ?
 C3 C4 1.402(2) . ?
 C3 C19 1.441(2) . ?
 C4 C46 1.394(2) . ?
 C5 C6 1.394(2) . ?
 C5 C44 1.392(2) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.378(2) . ?
 C7 C8 1.518(2) . ?
 C7 C42 1.402(2) . ?
 C8 H8 1.0000 . ?
 C8 C9 1.524(2) . ?
 C8 C23 1.513(2) . ?
 C9 C10 1.380(2) . ?
 C9 C32 1.395(2) . ?
 C10 H10 0.9500 . ?
 C10 C11 1.386(2) . ?
 C11 H11 0.9500 . ?
 C11 C12 1.389(2) . ?
 C12 C41 1.390(2) . ?
 C13 C14 1.391(2) . ?
 C13 C39 1.405(2) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.383(2) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.386(2) . ?
 C16 H16 0.9500 . ?
 C16 C40 1.381(2) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.366(3) . ?
 C17 C22 1.383(3) . ?
 C18 H18 0.9500 . ?
 C18 C19 1.394(2) . ?
 C19 C20 1.401(2) . ?
 C20 C21 1.382(2) . ?
 C21 H21 0.9500 . ?
 C21 C22 1.378(3) . ?
 C22 H22 0.9500 . ?
 C23 C30 1.432(2) . ?
 C24 C25 1.409(2) . ?
 C24 C29 1.405(2) . ?
 C25 H25 0.9500 . ?
 C25 C26 1.366(2) . ?
 C26 H26 0.9500 . ?
 C26 C27 1.392(3) . ?
 C27 H27 0.9500 . ?
 C27 C28 1.373(3) . ?
 C28 H28 0.9500 . ?
 C28 C29 1.407(2) . ?
 C30 C31 1.519(2) . ?
 C31 H31 1.0000 . ?
 C31 C32 1.528(2) . ?
 C31 C42 1.528(2) . ?
 C32 C41 1.386(2) . ?
 C33 C34 1.385(2) . ?
 C33 C38 1.406(2) . ?
 C34 H34 0.9500 . ?
 C34 C35 1.385(2) . ?
 C35 H35 0.9500 . ?
 C35 C36 1.393(2) . ?
 C36 H36 0.9500 . ?
 C36 C37 1.376(2) . ?
 C37 H37 0.9500 . ?
 C37 C38 1.387(2) . ?
 C38 C39 1.449(2) . ?
 C39 C40 1.393(2) . ?
 C40 H40 0.9500 . ?
 C41 H41 0.9500 . ?
 C42 C43 1.380(2) . ?
 C43 H43 0.9500 . ?
 C43 C44 1.389(2) . ?
 C44 H44 0.9500 . ?
 C45 H45 0.9500 . ?
 C45 C46 1.377(2) . ?
 C46 H46 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
 C4 N1 C5 125.85(13) . . ?
 C20 N1 C4 108.14(13) . . ?
 C20 N1 C5 125.63(12) . . ?
 C13 N2 C12 124.91(13) . . ?
 C33 N2 C12 126.39(13) . . ?
 C33 N2 C13 108.43(12) . . ?
 C23 N3 C24 114.60(13) . . ?
 C30 N4 C29 114.85(13) . . ?
 C2 C1 H1 119.3 . . ?
 C2 C1 C45 121.47(19) . . ?
 C45 C1 H1 119.3 . . ?
 C1 C2 H2 120.3 . . ?
 C1 C2 C3 119.3(2) . . ?
 C3 C2 H2 120.3 . . ?
 C2 C3 C4 118.43(18) . . ?
 C2 C3 C19 134.52(17) . . ?
 C4 C3 C19 106.99(14) . . ?
 N1 C4 C3 108.82(14) . . ?
 C46 C4 N1 129.14(15) . . ?
 C46 C4 C3 121.96(15) . . ?
 C6 C5 N1 119.28(13) . . ?
 C44 C5 N1 120.65(13) . . ?
 C44 C5 C6 120.07(14) . . ?
 C5 C6 H6 120.4 . . ?
 C7 C6 C5 119.14(14) . . ?
 C7 C6 H6 120.4 . . ?
 C6 C7 C8 125.60(13) . . ?
 C6 C7 C42 120.96(14) . . ?
 C42 C7 C8 113.43(13) . . ?
 C7 C8 H8 113.1 . . ?
 C7 C8 C9 105.39(12) . . ?
 C9 C8 H8 113.1 . . ?
 C23 C8 C7 105.30(11) . . ?
 C23 C8 H8 113.1 . . ?
 C23 C8 C9 106.01(11) . . ?
 C10 C9 C8 126.30(13) . . ?
 C10 C9 C32 120.03(14) . . ?
 C32 C9 C8 113.60(12) . . ?
 C9 C10 H10 120.1 . . ?
 C9 C10 C11 119.84(14) . . ?
 C11 C10 H10 120.1 . . ?
 C10 C11 H11 120.0 . . ?
 C10 C11 C12 120.02(14) . . ?
 C12 C11 H11 120.0 . . ?
 C11 C12 N2 119.04(13) . . ?
 C11 C12 C41 120.60(14) . . ?
 C41 C12 N2 120.32(13) . . ?
 N2 C13 C39 109.00(13) . . ?
 C14 C13 N2 129.32(14) . . ?
 C14 C13 C39 121.68(14) . . ?
 C13 C14 H14 121.3 . . ?
 C15 C14 C13 117.46(16) . . ?
 C15 C14 H14 121.3 . . ?
 C14 C15 H15 119.1 . . ?
 C14 C15 C16 121.70(16) . . ?
 C16 C15 H15 119.1 . . ?
 C15 C16 H16 119.7 . . ?
 C40 C16 C15 120.70(16) . . ?
 C40 C16 H16 119.7 . . ?
 C18 C17 H17 119.4 . . ?
 C18 C17 C22 121.13(18) . . ?
 C22 C17 H17 119.4 . . ?
 C17 C18 H18 120.4 . . ?
 C17 C18 C19 119.23(19) . . ?
 C19 C18 H18 120.4 . . ?
 C18 C19 C3 134.01(17) . . ?
 C18 C19 C20 118.73(17) . . ?
 C20 C19 C3 107.22(14) . . ?
 N1 C20 C19 108.82(14) . . ?
 C21 C20 N1 129.17(15) . . ?
 C21 C20 C19 122.00(16) . . ?
 C20 C21 H21 121.2 . . ?
 C22 C21 C20 117.53(18) . . ?
 C22 C21 H21 121.2 . . ?
 C17 C22 H22 119.4 . . ?
 C21 C22 C17 121.26(19) . . ?
 C21 C22 H22 119.4 . . ?
 N3 C23 C8 123.54(13) . . ?
 N3 C23 C30 123.48(14) . . ?
 C30 C23 C8 112.98(13) . . ?
 N3 C24 C25 118.73(15) . . ?
 N3 C24 C29 121.96(14) . . ?
 C29 C24 C25 119.30(15) . . ?
 C24 C25 H25 119.9 . . ?
 C26 C25 C24 120.16(17) . . ?
 C26 C25 H25 119.9 . . ?
 C25 C26 H26 119.8 . . ?
 C25 C26 C27 120.40(17) . . ?
 C27 C26 H26 119.8 . . ?
 C26 C27 H27 119.5 . . ?
 C28 C27 C26 120.94(17) . . ?
 C28 C27 H27 119.5 . . ?
 C27 C28 H28 120.2 . . ?
 C27 C28 C29 119.57(17) . . ?
 C29 C28 H28 120.2 . . ?
 N4 C29 C24 121.71(14) . . ?
 N4 C29 C28 118.67(15) . . ?
 C24 C29 C28 119.62(16) . . ?
 N4 C30 C23 123.38(14) . . ?
 N4 C30 C31 123.99(13) . . ?
 C23 C30 C31 112.62(13) . . ?
 C30 C31 H31 113.2 . . ?
 C30 C31 C32 105.59(12) . . ?
 C30 C31 C42 105.90(12) . . ?
 C32 C31 H31 113.2 . . ?
 C32 C31 C42 104.95(11) . . ?
 C42 C31 H31 113.2 . . ?
 C9 C32 C31 113.23(13) . . ?
 C41 C32 C9 120.57(13) . . ?
 C41 C32 C31 126.09(13) . . ?
 N2 C33 C38 108.82(13) . . ?
 C34 C33 N2 129.46(14) . . ?
 C34 C33 C38 121.70(15) . . ?
 C33 C34 H34 121.3 . . ?
 C35 C34 C33 117.45(16) . . ?
 C35 C34 H34 121.3 . . ?
 C34 C35 H35 119.3 . . ?
 C34 C35 C36 121.44(16) . . ?
 C36 C35 H35 119.3 . . ?
 C35 C36 H36 119.6 . . ?
 C37 C36 C35 120.74(16) . . ?
 C37 C36 H36 119.6 . . ?
 C36 C37 H37 120.4 . . ?
 C36 C37 C38 119.12(16) . . ?
 C38 C37 H37 120.4 . . ?
 C33 C38 C39 106.98(13) . . ?
 C37 C38 C33 119.53(15) . . ?
 C37 C38 C39 133.45(15) . . ?
 C13 C39 C38 106.76(13) . . ?
 C40 C39 C13 119.31(15) . . ?
 C40 C39 C38 133.93(15) . . ?
 C16 C40 C39 119.15(16) . . ?
 C16 C40 H40 120.4 . . ?
 C39 C40 H40 120.4 . . ?
 C12 C41 H41 120.5 . . ?
 C32 C41 C12 118.92(14) . . ?
 C32 C41 H41 120.5 . . ?
 C7 C42 C31 113.17(13) . . ?
 C43 C42 C7 119.55(14) . . ?
 C43 C42 C31 127.24(13) . . ?
 C42 C43 H43 120.1 . . ?
 C42 C43 C44 119.85(14) . . ?
 C44 C43 H43 120.1 . . ?
 C5 C44 H44 119.8 . . ?
 C43 C44 C5 120.33(14) . . ?
 C43 C44 H44 119.8 . . ?
 C1 C45 H45 119.4 . . ?
 C1 C45 C46 121.2(2) . . ?
 C46 C45 H45 119.4 . . ?
 C4 C46 H46 121.2 . . ?
 C45 C46 C4 117.61(18) . . ?
 C45 C46 H46 121.2 . . ?

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
 N1 C4 C46 C45 177.25(17) . . . . ?
 N1 C5 C6 C7 -178.03(13) . . . . ?
 N1 C5 C44 C43 -179.10(13) . . . . ?
 N1 C20 C21 C22 -176.78(17) . . . . ?
 N2 C12 C41 C32 -178.23(13) . . . . ?
 N2 C13 C14 C15 179.35(15) . . . . ?
 N2 C13 C39 C38 -0.56(17) . . . . ?
 N2 C13 C39 C40 179.98(14) . . . . ?
 N2 C33 C34 C35 -178.24(16) . . . . ?
 N2 C33 C38 C37 178.77(14) . . . . ?
 N2 C33 C38 C39 0.57(17) . . . . ?
 N3 C23 C30 N4 -0.7(2) . . . . ?
 N3 C23 C30 C31 179.44(13) . . . . ?
 N3 C24 C25 C26 -179.37(15) . . . . ?
 N3 C24 C29 N4 -0.8(2) . . . . ?
 N3 C24 C29 C28 179.10(14) . . . . ?
 N4 C30 C31 C32 -124.14(15) . . . . ?
 N4 C30 C31 C42 124.88(15) . . . . ?
 C1 C2 C3 C4 1.2(3) . . . . ?
 C1 C2 C3 C19 -175.4(2) . . . . ?
 C1 C45 C46 C4 0.7(3) . . . . ?
 C2 C1 C45 C46 -1.2(4) . . . . ?
 C2 C3 C4 N1 -178.85(16) . . . . ?
 C2 C3 C4 C46 -1.8(3) . . . . ?
 C2 C3 C19 C18 0.5(4) . . . . ?
 C2 C3 C19 C20 177.9(2) . . . . ?
 C3 C4 C46 C45 0.8(3) . . . . ?
 C3 C19 C20 N1 -0.33(19) . . . . ?
 C3 C19 C20 C21 179.38(16) . . . . ?
 C4 N1 C5 C6 51.1(2) . . . . ?
 C4 N1 C5 C44 -127.95(16) . . . . ?
 C4 N1 C20 C19 -0.51(18) . . . . ?
 C4 N1 C20 C21 179.81(17) . . . . ?
 C4 C3 C19 C18 -176.4(2) . . . . ?
 C4 C3 C19 C20 1.04(19) . . . . ?
 C5 N1 C4 C3 174.39(15) . . . . ?
 C5 N1 C4 C46 -2.4(3) . . . . ?
 C5 N1 C20 C19 -173.74(14) . . . . ?
 C5 N1 C20 C21 6.6(3) . . . . ?
 C5 C6 C7 C8 175.43(13) . . . . ?
 C5 C6 C7 C42 -3.2(2) . . . . ?
 C6 C5 C44 C43 1.8(2) . . . . ?
 C6 C7 C8 C9 -124.26(15) . . . . ?
 C6 C7 C8 C23 123.90(15) . . . . ?
 C6 C7 C42 C31 -179.50(13) . . . . ?
 C6 C7 C42 C43 2.4(2) . . . . ?
 C7 C8 C9 C10 120.68(15) . . . . ?
 C7 C8 C9 C32 -56.16(15) . . . . ?
 C7 C8 C23 N3 -123.39(15) . . . . ?
 C7 C8 C23 C30 56.22(15) . . . . ?
 C7 C42 C43 C44 0.5(2) . . . . ?
 C8 C7 C42 C31 1.72(17) . . . . ?
 C8 C7 C42 C43 -176.34(13) . . . . ?
 C8 C9 C10 C11 -177.95(14) . . . . ?
 C8 C9 C32 C31 0.90(18) . . . . ?
 C8 C9 C32 C41 177.34(13) . . . . ?
 C8 C23 C30 N4 179.70(13) . . . . ?
 C8 C23 C30 C31 -0.17(17) . . . . ?
 C9 C8 C23 N3 125.22(15) . . . . ?
 C9 C8 C23 C30 -55.18(15) . . . . ?
 C9 C10 C11 C12 1.5(2) . . . . ?
 C9 C32 C41 C12 0.5(2) . . . . ?
 C10 C9 C32 C31 -176.15(13) . . . . ?
 C10 C9 C32 C41 0.3(2) . . . . ?
 C10 C11 C12 N2 177.25(14) . . . . ?
 C10 C11 C12 C41 -0.7(2) . . . . ?
 C11 C12 C41 C32 -0.3(2) . . . . ?
 C12 N2 C13 C14 -4.7(2) . . . . ?
 C12 N2 C13 C39 175.29(14) . . . . ?
 C12 N2 C33 C34 3.3(3) . . . . ?
 C12 N2 C33 C38 -175.19(14) . . . . ?
 C13 N2 C12 C11 -45.9(2) . . . . ?
 C13 N2 C12 C41 132.08(16) . . . . ?
 C13 N2 C33 C34 177.59(16) . . . . ?
 C13 N2 C33 C38 -0.93(17) . . . . ?
 C13 C14 C15 C16 0.6(2) . . . . ?
 C13 C39 C40 C16 0.7(2) . . . . ?
 C14 C13 C39 C38 179.44(14) . . . . ?
 C14 C13 C39 C40 0.0(2) . . . . ?
 C14 C15 C16 C40 0.1(3) . . . . ?
 C15 C16 C40 C39 -0.8(3) . . . . ?
 C17 C18 C19 C3 176.92(19) . . . . ?
 C17 C18 C19 C20 -0.3(3) . . . . ?
 C18 C17 C22 C21 -1.4(3) . . . . ?
 C18 C19 C20 N1 177.61(16) . . . . ?
 C18 C19 C20 C21 -2.7(3) . . . . ?
 C19 C3 C4 N1 -1.37(19) . . . . ?
 C19 C3 C4 C46 175.71(16) . . . . ?
 C19 C20 C21 C22 3.6(3) . . . . ?
 C20 N1 C4 C3 1.18(18) . . . . ?
 C20 N1 C4 C46 -175.63(17) . . . . ?
 C20 N1 C5 C6 -136.82(16) . . . . ?
 C20 N1 C5 C44 44.1(2) . . . . ?
 C20 C21 C22 C17 -1.5(3) . . . . ?
 C22 C17 C18 C19 2.3(3) . . . . ?
 C23 N3 C24 C25 179.89(14) . . . . ?
 C23 N3 C24 C29 0.6(2) . . . . ?
 C23 C8 C9 C10 -127.99(15) . . . . ?
 C23 C8 C9 C32 55.17(16) . . . . ?
 C23 C30 C31 C32 55.73(16) . . . . ?
 C23 C30 C31 C42 -55.25(15) . . . . ?
 C24 N3 C23 C8 179.66(12) . . . . ?
 C24 N3 C23 C30 0.1(2) . . . . ?
 C24 C25 C26 C27 0.4(3) . . . . ?
 C25 C24 C29 N4 179.91(15) . . . . ?
 C25 C24 C29 C28 -0.2(2) . . . . ?
 C25 C26 C27 C28 -0.4(3) . . . . ?
 C26 C27 C28 C29 0.2(3) . . . . ?
 C27 C28 C29 N4 -179.96(15) . . . . ?
 C27 C28 C29 C24 0.1(2) . . . . ?
 C29 N4 C30 C23 0.5(2) . . . . ?
 C29 N4 C30 C31 -179.66(13) . . . . ?
 C29 C24 C25 C26 -0.1(2) . . . . ?
 C30 N4 C29 C24 0.2(2) . . . . ?
 C30 N4 C29 C28 -179.69(14) . . . . ?
 C30 C31 C32 C9 -56.51(16) . . . . ?
 C30 C31 C32 C41 127.29(15) . . . . ?
 C30 C31 C42 C7 54.73(15) . . . . ?
 C30 C31 C42 C43 -127.39(16) . . . . ?
 C31 C32 C41 C12 176.46(14) . . . . ?
 C31 C42 C43 C44 -177.27(13) . . . . ?
 C32 C9 C10 C11 -1.3(2) . . . . ?
 C32 C31 C42 C7 -56.70(15) . . . . ?
 C32 C31 C42 C43 121.19(16) . . . . ?
 C33 N2 C12 C11 127.46(16) . . . . ?
 C33 N2 C12 C41 -54.6(2) . . . . ?
 C33 N2 C13 C14 -179.08(15) . . . . ?
 C33 N2 C13 C39 0.92(17) . . . . ?
 C33 C34 C35 C36 -0.8(3) . . . . ?
 C33 C38 C39 C13 -0.01(17) . . . . ?
 C33 C38 C39 C40 179.34(17) . . . . ?
 C34 C33 C38 C37 0.1(2) . . . . ?
 C34 C33 C38 C39 -178.09(14) . . . . ?
 C34 C35 C36 C37 1.2(3) . . . . ?
 C35 C36 C37 C38 -0.9(3) . . . . ?
 C36 C37 C38 C33 0.3(2) . . . . ?
 C36 C37 C38 C39 177.91(17) . . . . ?
 C37 C38 C39 C13 -177.85(17) . . . . ?
 C37 C38 C39 C40 1.5(3) . . . . ?
 C38 C33 C34 C35 0.1(2) . . . . ?
 C38 C39 C40 C16 -178.55(17) . . . . ?
 C39 C13 C14 C15 -0.6(2) . . . . ?
 C42 C7 C8 C9 54.45(15) . . . . ?
 C42 C7 C8 C23 -57.38(15) . . . . ?
 C42 C31 C32 C9 55.14(16) . . . . ?
 C42 C31 C32 C41 -121.07(16) . . . . ?
 C42 C43 C44 C5 -2.6(2) . . . . ?
 C44 C5 C6 C7 1.1(2) . . . . ?
 C45 C1 C2 C3 0.2(4) . . . . ?

_smtbx_masks_special_details       ?
loop_
  _smtbx_masks_void_nr
  _smtbx_masks_void_average_x
  _smtbx_masks_void_average_y
  _smtbx_masks_void_average_z
  _smtbx_masks_void_volume
  _smtbx_masks_void_count_electrons
  _smtbx_masks_void_content
 1 0.000 0.500 0.000 411.5 100.2 ?
 2 0.500 0.000 0.500 411.5 100.2 ?

_olex2_submission_special_instructions  'No special instructions were received'
