# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1817912'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H29 N5 O3'
_chemical_formula_weight         615.67

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      tetragonal
_space_group_IT_number           114
_space_group_name_H-M_alt        'P -4 21 c'
_space_group_name_Hall           'P -4 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'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   29.3188(9)
_cell_length_b                   29.3188(9)
_cell_length_c                   8.8681(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7622.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      19.51

_exptl_crystal_description       rod
_exptl_crystal_colour            dark-purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_F_000             2576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.996
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            136520
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         30.090
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11201
_reflns_number_gt                4952
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0824P)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 1719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11201
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1626
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1680
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.004
_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 0.45336(16) 0.29700(19) 0.9157(6) 0.0909(14) Uani 1 1 d . . . . .
H1 H 0.447213 0.320176 0.843678 0.109 Uiso 1 1 calc R U . . .
C2 C 0.42653(15) 0.2868(2) 1.0412(7) 0.0950(16) Uani 1 1 d . . . . .
H2 H 0.399341 0.301876 1.071231 0.114 Uiso 1 1 calc R U . . .
C3 C 0.44694(15) 0.25070(18) 1.1130(5) 0.0808(14) Uani 1 1 d . . . . .
H3 H 0.435905 0.236373 1.201871 0.097 Uiso 1 1 calc R U . . .
C4 C 0.48667(13) 0.23821(16) 1.0347(5) 0.0687(7) Uani 1 1 d . . . . .
C5 C 0.51929(12) 0.20434(14) 1.0610(4) 0.0548(9) Uani 1 1 d . . . . .
C6 C 0.55720(12) 0.19613(13) 0.9732(4) 0.0522(9) Uani 1 1 d . . . . .
C7 C 0.59109(13) 0.16166(14) 0.9926(4) 0.0599(10) Uani 1 1 d . . . . .
H7 H 0.592008 0.139373 1.070296 0.072 Uiso 1 1 calc R U . . .
C8 C 0.62226(12) 0.16679(13) 0.8773(4) 0.0566(10) Uani 1 1 d . . . . .
H8 H 0.648974 0.149215 0.859877 0.068 Uiso 1 1 calc R U . . .
C9 C 0.60569(12) 0.20438(13) 0.7891(4) 0.0516(9) Uani 1 1 d . . . . .
C10 C 0.51274(11) 0.17520(13) 1.1981(4) 0.0548(9) Uani 1 1 d . . . . .
C11 C 0.54170(13) 0.17900(14) 1.3208(4) 0.0615(10) Uani 1 1 d . . . . .
H11 H 0.565224 0.201270 1.319065 0.074 Uiso 1 1 calc R U . . .
C12 C 0.53722(13) 0.15128(13) 1.4451(4) 0.0565(9) Uani 1 1 d . . . . .
H12 H 0.557766 0.154045 1.527412 0.068 Uiso 1 1 calc R U . . .
C13 C 0.50253(12) 0.11938(12) 1.4491(4) 0.0505(9) Uani 1 1 d . . . . .
C14 C 0.47396(14) 0.11505(15) 1.3300(5) 0.0683(12) Uani 1 1 d . . . . .
H14 H 0.450554 0.092656 1.333130 0.082 Uiso 1 1 calc R U . . .
C15 C 0.47814(13) 0.14271(15) 1.2031(5) 0.0695(11) Uani 1 1 d . . . . .
H15 H 0.457615 0.139451 1.120961 0.083 Uiso 1 1 calc R U . . .
C16 C 0.49605(14) 0.08775(13) 1.5804(4) 0.0572(10) Uani 1 1 d . . . . .
C17 C 0.52273(16) 0.06588(16) 1.8232(6) 0.0863(14) Uani 1 1 d . . . . .
H17A H 0.493539 0.071609 1.873671 0.129 Uiso 1 1 calc R U . . .
H17B H 0.547805 0.072564 1.892875 0.129 Uiso 1 1 calc R U . . .
H17C H 0.524293 0.033838 1.792220 0.129 Uiso 1 1 calc R U . . .
C18 C 0.62742(11) 0.22178(12) 0.6569(4) 0.0467(8) Uani 1 1 d . . . . .
C19 C 0.67152(12) 0.21477(13) 0.6019(4) 0.0547(9) Uani 1 1 d . . . . .
H19 H 0.694237 0.196020 0.646554 0.066 Uiso 1 1 calc R U . . .
C20 C 0.67624(12) 0.23997(12) 0.4711(4) 0.0523(9) Uani 1 1 d . . . . .
H20 H 0.702900 0.241912 0.410542 0.063 Uiso 1 1 calc R U . . .
C21 C 0.63449(11) 0.26226(12) 0.4435(4) 0.0475(8) Uani 1 1 d . . . . .
C22 C 0.62147(11) 0.28964(12) 0.3187(4) 0.0469(8) Uani 1 1 d . . . . .
C23 C 0.57780(12) 0.30720(13) 0.2990(4) 0.0577(10) Uani 1 1 d . . . . .
C24 C 0.56224(14) 0.33747(15) 0.1799(5) 0.0724(12) Uani 1 1 d . . . . .
H24 H 0.579473 0.348543 0.096925 0.087 Uiso 1 1 calc R U . . .
C25 C 0.51794(15) 0.34661(17) 0.2122(5) 0.0825(13) Uani 1 1 d . . . . .
H25 H 0.497799 0.365490 0.156108 0.099 Uiso 1 1 calc R U . . .
C26 C 0.50744(15) 0.32182(17) 0.3495(5) 0.0818(13) Uani 1 1 d . . . . .
H26 H 0.478380 0.322428 0.396836 0.098 Uiso 1 1 calc R U . . .
C27 C 0.65799(11) 0.29970(11) 0.2073(4) 0.0477(8) Uani 1 1 d . . . . .
C28 C 0.69710(12) 0.32258(12) 0.2536(3) 0.0523(9) Uani 1 1 d . . . . .
H28 H 0.699033 0.334242 0.353304 0.063 Uiso 1 1 calc R U . . .
C29 C 0.73332(12) 0.32846(12) 0.1547(4) 0.0516(9) Uani 1 1 d . . . . .
H29 H 0.759910 0.344187 0.186982 0.062 Uiso 1 1 calc R U . . .
C30 C 0.73085(12) 0.31155(11) 0.0099(4) 0.0447(8) Uani 1 1 d . . . . .
C31 C 0.69127(11) 0.29098(11) -0.0395(3) 0.0459(8) Uani 1 1 d . . . . .
H31 H 0.688885 0.280935 -0.141007 0.055 Uiso 1 1 calc R U . . .
C32 C 0.65541(12) 0.28498(12) 0.0573(4) 0.0472(8) Uani 1 1 d . . . . .
H32 H 0.628372 0.270627 0.022218 0.057 Uiso 1 1 calc R U . . .
C33 C 0.77127(11) 0.31648(11) -0.0927(3) 0.0448(8) Uani 1 1 d . . . . .
C34 C 0.85593(12) 0.31515(12) -0.0875(3) 0.0468(8) Uani 1 1 d . . . . .
C35 C 0.89066(13) 0.28748(13) -0.0312(4) 0.0567(10) Uani 1 1 d . . . . .
H35 H 0.884747 0.267068 0.049640 0.068 Uiso 1 1 calc R U . . .
C36 C 0.93351(13) 0.28994(15) -0.0936(5) 0.0660(11) Uani 1 1 d . . . . .
H36 H 0.957369 0.271654 -0.053604 0.079 Uiso 1 1 calc R U . . .
C37 C 0.94232(15) 0.31843(15) -0.2128(5) 0.0701(12) Uani 1 1 d . . . . .
H37 H 0.971563 0.318509 -0.258916 0.084 Uiso 1 1 calc R U . . .
C38 C 0.90902(16) 0.34647(14) -0.2644(5) 0.0671(11) Uani 1 1 d . . . . .
H38 H 0.915743 0.366898 -0.344524 0.081 Uiso 1 1 calc R U . . .
C39 C 0.86582(13) 0.34620(12) -0.2042(4) 0.0563(9) Uani 1 1 d . . . . .
H39 H 0.843113 0.366535 -0.240525 0.068 Uiso 1 1 calc R U . . .
N1 N 0.48931(11) 0.26864(12) 0.9137(4) 0.0687(7) Uani 1 1 d . . . . .
H1A H 0.511290 0.269136 0.846160 0.082 Uiso 1 1 calc R U . . .
N2 N 0.56689(9) 0.22172(10) 0.8427(3) 0.0520(7) Uani 1 1 d . . . . .
N3 N 0.60536(10) 0.25071(10) 0.5599(3) 0.0522(8) Uani 1 1 d . . . . .
H3A H 0.577127 0.260408 0.570164 0.063 Uiso 1 1 calc R U . . .
N4 N 0.54186(11) 0.29871(12) 0.4010(4) 0.0660(9) Uani 1 1 d . . . . .
N5 N 0.81174(9) 0.31161(10) -0.0225(3) 0.0511(7) Uani 1 1 d . . . . .
H5 H 0.810697 0.305550 0.074633 0.061 Uiso 1 1 calc R U . . .
O1 O 0.46657(10) 0.05960(10) 1.5873(3) 0.0794(9) Uani 1 1 d . . . . .
O2 O 0.52652(9) 0.09528(9) 1.6899(3) 0.0691(7) Uani 1 1 d . . . . .
O3 O 0.76705(8) 0.32296(8) -0.2286(2) 0.0566(6) 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 1.342(6) . ?
C1 C2 1.396(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(6) . ?
C3 H3 0.9500 . ?
C4 N1 1.398(5) . ?
C4 C5 1.398(6) . ?
C5 C6 1.378(5) . ?
C5 C10 1.498(5) . ?
C6 N2 1.408(4) . ?
C6 C7 1.428(5) . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.436(5) . ?
C8 H8 0.9500 . ?
C9 N2 1.333(4) . ?
C9 C18 1.429(5) . ?
C10 C11 1.385(5) . ?
C10 C15 1.392(5) . ?
C11 C12 1.376(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.353(5) . ?
C13 C16 1.501(5) . ?
C14 C15 1.393(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O1 1.197(4) . ?
C16 O2 1.338(5) . ?
C17 O2 1.467(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N3 1.370(5) . ?
C18 C19 1.397(5) . ?
C19 C20 1.383(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.409(5) . ?
C20 H20 0.9500 . ?
C21 N3 1.382(4) . ?
C21 C22 1.419(5) . ?
C22 C23 1.391(5) . ?
C22 C27 1.487(5) . ?
C23 N4 1.411(5) . ?
C23 C24 1.453(6) . ?
C24 C25 1.357(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.451(7) . ?
C25 H25 0.9500 . ?
C26 N4 1.298(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(5) . ?
C27 C32 1.400(5) . ?
C28 C29 1.388(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.379(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.379(5) . ?
C30 C33 1.501(5) . ?
C31 C32 1.368(5) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 O3 1.227(4) . ?
C33 N5 1.347(4) . ?
C34 C35 1.394(5) . ?
C34 C39 1.409(5) . ?
C34 N5 1.422(4) . ?
C35 C36 1.375(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.372(6) . ?
C36 H36 0.9500 . ?
C37 C38 1.356(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.374(5) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
N1 H1A 0.8800 . ?
N3 H3A 0.8800 . ?
N5 H5 0.8800 . ?

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 108.7(5) . . ?
N1 C1 H1 125.7 . . ?
C2 C1 H1 125.7 . . ?
C3 C2 C1 106.8(4) . . ?
C3 C2 H2 126.6 . . ?
C1 C2 H2 126.6 . . ?
C2 C3 C4 109.5(4) . . ?
C2 C3 H3 125.3 . . ?
C4 C3 H3 125.3 . . ?
N1 C4 C5 122.9(4) . . ?
N1 C4 C3 105.0(4) . . ?
C5 C4 C3 132.1(4) . . ?
C6 C5 C4 125.6(4) . . ?
C6 C5 C10 117.5(3) . . ?
C4 C5 C10 116.9(3) . . ?
C5 C6 N2 122.3(3) . . ?
C5 C6 C7 128.1(3) . . ?
N2 C6 C7 109.6(3) . . ?
C8 C7 C6 107.1(3) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 105.2(3) . . ?
C7 C8 H8 127.4 . . ?
C9 C8 H8 127.4 . . ?
N2 C9 C18 122.5(3) . . ?
N2 C9 C8 112.8(3) . . ?
C18 C9 C8 124.7(3) . . ?
C11 C10 C15 118.4(3) . . ?
C11 C10 C5 120.9(3) . . ?
C15 C10 C5 120.7(3) . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 C16 118.0(3) . . ?
C12 C13 C16 122.1(3) . . ?
C13 C14 C15 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C10 C15 C14 119.3(3) . . ?
C10 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
O1 C16 O2 124.0(4) . . ?
O1 C16 C13 123.9(4) . . ?
O2 C16 C13 112.1(3) . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C19 108.0(3) . . ?
N3 C18 C9 121.7(3) . . ?
C19 C18 C9 130.3(4) . . ?
C20 C19 C18 107.9(3) . . ?
C20 C19 H19 126.1 . . ?
C18 C19 H19 126.1 . . ?
C19 C20 C21 107.9(3) . . ?
C19 C20 H20 126.1 . . ?
C21 C20 H20 126.1 . . ?
N3 C21 C20 107.0(3) . . ?
N3 C21 C22 123.7(3) . . ?
C20 C21 C22 129.2(3) . . ?
C23 C22 C21 123.7(3) . . ?
C23 C22 C27 120.4(3) . . ?
C21 C22 C27 115.9(3) . . ?
C22 C23 N4 122.8(3) . . ?
C22 C23 C24 127.3(4) . . ?
N4 C23 C24 109.8(3) . . ?
C25 C24 C23 105.5(4) . . ?
C25 C24 H24 127.2 . . ?
C23 C24 H24 127.2 . . ?
C24 C25 C26 106.3(4) . . ?
C24 C25 H25 126.8 . . ?
C26 C25 H25 126.8 . . ?
N4 C26 C25 113.1(4) . . ?
N4 C26 H26 123.5 . . ?
C25 C26 H26 123.5 . . ?
C28 C27 C32 118.3(3) . . ?
C28 C27 C22 119.5(3) . . ?
C32 C27 C22 122.1(3) . . ?
C29 C28 C27 120.3(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 119.8(3) . . ?
C29 C30 C33 119.2(3) . . ?
C31 C30 C33 120.9(3) . . ?
C32 C31 C30 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C27 121.0(3) . . ?
C31 C32 H32 119.5 . . ?
C27 C32 H32 119.5 . . ?
O3 C33 N5 124.0(3) . . ?
O3 C33 C30 122.1(3) . . ?
N5 C33 C30 113.9(3) . . ?
C35 C34 C39 119.3(3) . . ?
C35 C34 N5 118.6(3) . . ?
C39 C34 N5 122.2(3) . . ?
C36 C35 C34 119.5(4) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
C37 C36 C35 120.9(4) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C38 C37 C36 119.6(4) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C37 C38 C39 121.9(4) . . ?
C37 C38 H38 119.0 . . ?
C39 C38 H38 119.0 . . ?
C38 C39 C34 118.6(4) . . ?
C38 C39 H39 120.7 . . ?
C34 C39 H39 120.7 . . ?
C1 N1 C4 110.0(4) . . ?
C1 N1 H1A 125.0 . . ?
C4 N1 H1A 125.0 . . ?
C9 N2 C6 105.2(3) . . ?
C18 N3 C21 109.2(3) . . ?
C18 N3 H3A 125.4 . . ?
C21 N3 H3A 125.4 . . ?
C26 N4 C23 105.3(3) . . ?
C33 N5 C34 127.4(3) . . ?
C33 N5 H5 116.3 . . ?
C34 N5 H5 116.3 . . ?
C16 O2 C17 115.9(3) . . ?

_refine_diff_density_max         0.153
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.037


####################################################################### 
# 
# 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_compound11
_database_code_depnum_ccdc_archive 'CCDC 1817915'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H41 N5 O'
_chemical_formula_weight         655.82

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                   23.5417(12)
_cell_length_b                   16.6120(8)
_cell_length_c                   9.1741(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.111(2)
_cell_angle_gamma                90
_cell_volume                     3532.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      22.52

_exptl_crystal_description       platelet
_exptl_crystal_colour            dark-purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_T_max  0.996
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            71159
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.143
_diffrn_reflns_theta_max         30.227
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10445
_reflns_number_gt                5464
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1081P)²+1.8065P] 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         10445
_refine_ls_number_parameters     452
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1542
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2430
_refine_ls_wR_factor_gt          0.2005
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.049
_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 0.62873(14) 0.54355(17) 0.0320(3) 0.0572(7) Uani 1 1 d . . . . .
H1 H 0.590656 0.563056 -0.000074 0.069 Uiso 1 1 calc R U . . .
C2 C 0.67795(14) 0.57232(18) -0.0147(3) 0.0595(8) Uani 1 1 d . . . . .
H2 H 0.679584 0.614510 -0.083757 0.071 Uiso 1 1 calc R U . . .
C3 C 0.72373(12) 0.52849(16) 0.0574(3) 0.0509(6) Uani 1 1 d . . . . .
H3 H 0.762952 0.534920 0.047332 0.061 Uiso 1 1 calc R U . . .
C4 C 0.70240(10) 0.47242(15) 0.1489(3) 0.0416(5) Uani 1 1 d . . . . .
C5 C 0.73180(10) 0.41309(14) 0.2434(3) 0.0399(5) Uani 1 1 d . . . . .
C6 C 0.70358(10) 0.35803(14) 0.3218(3) 0.0393(5) Uani 1 1 d . . . . .
C7 C 0.72663(11) 0.29433(16) 0.4193(3) 0.0493(6) Uani 1 1 d . . . . .
H7 H 0.766098 0.279449 0.444621 0.059 Uiso 1 1 calc R U . . .
C8 C 0.68186(11) 0.25927(17) 0.4686(3) 0.0506(6) Uani 1 1 d . . . . .
H8 H 0.683799 0.214489 0.533699 0.061 Uiso 1 1 calc R U . . .
C9 C 0.63127(10) 0.30198(15) 0.4048(3) 0.0415(5) Uani 1 1 d . . . . .
C10 C 0.79543(10) 0.41041(15) 0.2609(3) 0.0428(6) Uani 1 1 d . . . . .
C11 C 0.82781(11) 0.47860(16) 0.3112(3) 0.0470(6) Uani 1 1 d . . . . .
H11 H 0.808683 0.527048 0.328910 0.056 Uiso 1 1 calc R U . . .
C12 C 0.88717(11) 0.47617(18) 0.3354(3) 0.0543(7) Uani 1 1 d . . . . .
H12 H 0.908238 0.523207 0.370120 0.065 Uiso 1 1 calc R U . . .
C13 C 0.91703(12) 0.40733(19) 0.3106(4) 0.0593(7) Uani 1 1 d . . . . .
C14 C 0.88478(13) 0.34073(19) 0.2572(4) 0.0681(9) Uani 1 1 d . . . . .
H14 H 0.904137 0.293104 0.236005 0.082 Uiso 1 1 calc R U . . .
C15 C 0.82527(12) 0.34144(18) 0.2338(4) 0.0588(7) Uani 1 1 d . . . . .
H15 H 0.804469 0.294242 0.198809 0.071 Uiso 1 1 calc R U . . .
C16 C 0.98198(13) 0.4068(3) 0.3410(5) 0.0907(12) Uani 1 1 d . . . . .
H16A H 0.996405 0.451841 0.288815 0.136 Uiso 1 1 calc R U . . .
H16B H 0.995993 0.356003 0.306309 0.136 Uiso 1 1 calc R U . . .
H16C H 0.995822 0.412381 0.447681 0.136 Uiso 1 1 calc R U . . .
C17 C 0.57329(10) 0.29332(14) 0.4289(3) 0.0399(5) Uani 1 1 d . . . . .
C18 C 0.54703(10) 0.23527(15) 0.5070(3) 0.0448(6) Uani 1 1 d . . . . .
H18 H 0.564870 0.188645 0.554544 0.054 Uiso 1 1 calc R U . . .
C19 C 0.49040(10) 0.25891(15) 0.5013(3) 0.0434(6) Uani 1 1 d . . . . .
H19 H 0.461948 0.231042 0.543400 0.052 Uiso 1 1 calc R U . . .
C20 C 0.48254(9) 0.33151(14) 0.4223(2) 0.0370(5) Uani 1 1 d . . . . .
C21 C 0.43549(9) 0.38640(14) 0.4007(2) 0.0365(5) Uani 1 1 d . . . . .
C22 C 0.43763(10) 0.46340(14) 0.3442(2) 0.0390(5) Uani 1 1 d . . . . .
C23 C 0.39424(11) 0.52408(15) 0.3224(3) 0.0444(6) Uani 1 1 d . . . . .
H23 H 0.356364 0.519706 0.344060 0.053 Uiso 1 1 calc R U . . .
C24 C 0.41701(13) 0.58924(16) 0.2648(3) 0.0528(7) Uani 1 1 d . . . . .
H24 H 0.398307 0.639163 0.238550 0.063 Uiso 1 1 calc R U . . .
C25 C 0.47424(12) 0.56819(16) 0.2515(3) 0.0522(7) Uani 1 1 d . . . . .
H25 H 0.500122 0.603221 0.213921 0.063 Uiso 1 1 calc R U . . .
C26 C 0.38086(9) 0.35866(14) 0.4447(2) 0.0349(5) Uani 1 1 d . . . . .
C27 C 0.35194(9) 0.29173(14) 0.3769(2) 0.0363(5) Uani 1 1 d . . . . .
H27 H 0.368661 0.261759 0.307050 0.044 Uiso 1 1 calc R U . . .
C28 C 0.29924(9) 0.26811(14) 0.4097(2) 0.0351(5) Uani 1 1 d . . . . .
H28 H 0.279760 0.222922 0.360837 0.042 Uiso 1 1 calc R U . . .
C29 C 0.27471(9) 0.31032(13) 0.5138(2) 0.0338(5) Uani 1 1 d . . . . .
C30 C 0.30491(10) 0.37505(14) 0.5870(2) 0.0400(5) Uani 1 1 d . . . . .
H30 H 0.289449 0.402917 0.661575 0.048 Uiso 1 1 calc R U . . .
C31 C 0.35701(10) 0.39903(15) 0.5521(3) 0.0413(5) Uani 1 1 d . . . . .
H31 H 0.376812 0.443657 0.602180 0.050 Uiso 1 1 calc R U . . .
C32 C 0.21707(9) 0.29052(14) 0.5525(2) 0.0354(5) Uani 1 1 d . . . . .
C33 C 0.12576(10) 0.21720(16) 0.4703(3) 0.0449(6) Uani 1 1 d . . . . .
C34 C 0.09055(11) 0.25980(19) 0.5492(3) 0.0577(7) Uani 1 1 d . . . . .
H34 H 0.103995 0.307960 0.599565 0.069 Uiso 1 1 calc R U . . .
C35 C 0.03590(13) 0.2316(2) 0.5538(4) 0.0732(9) Uani 1 1 d . . . . .
H35 H 0.011971 0.260256 0.609138 0.088 Uiso 1 1 calc R U . . .
C36 C 0.01542(14) 0.1631(3) 0.4801(4) 0.0792(11) Uani 1 1 d . . . . .
H36 H -0.022785 0.145203 0.481758 0.095 Uiso 1 1 calc R U . . .
C37 C 0.05076(14) 0.1204(2) 0.4037(4) 0.0798(11) Uani 1 1 d . . . . .
H37 H 0.037176 0.072236 0.353542 0.096 Uiso 1 1 calc R U . . .
C38 C 0.10612(12) 0.1475(2) 0.3997(3) 0.0616(8) Uani 1 1 d . . . . .
H38 H 0.130534 0.117525 0.347629 0.074 Uiso 1 1 calc R U . . .
N1 N 0.64349(9) 0.48406(13) 0.1292(2) 0.0472(5) Uani 1 1 d . . . . .
H1A H 0.619472 0.456643 0.173707 0.057 Uiso 1 1 calc R U . . .
N2 N 0.64442(8) 0.36039(12) 0.3156(2) 0.0409(5) Uani 1 1 d . . . . .
N3 N 0.53374(8) 0.34982(12) 0.3785(2) 0.0387(4) Uani 1 1 d . . . . .
H3A H 0.539838 0.392080 0.325475 0.046 Uiso 1 1 calc R U . . .
N4 N 0.48720(9) 0.49440(13) 0.2974(2) 0.0458(5) Uani 1 1 d . . . . .
N5 N 0.18225(8) 0.24332(13) 0.4575(2) 0.0417(5) Uani 1 1 d . . . . .
H5 H 0.195711 0.226771 0.378984 0.050 Uiso 1 1 calc R U . . .
O1 O 0.20316(7) 0.31825(10) 0.66611(17) 0.0433(4) Uani 1 1 d . . . . .
C39 C 0.1359(2) 0.4550(2) 0.2807(5) 0.0958(13) Uani 1 1 d D . . . .
H39A H 0.139173 0.452383 0.389656 0.115 Uiso 1 1 calc R U . . .
H39B H 0.112286 0.408709 0.237474 0.115 Uiso 1 1 calc R U . . .
C40 C 0.1058(2) 0.5336(3) 0.2237(10) 0.191(4) Uani 1 1 d D . . . .
H40A H 0.095505 0.530688 0.114440 0.229 Uiso 1 1 calc R U . . .
H40B H 0.069379 0.538264 0.263245 0.229 Uiso 1 1 calc R U . . .
C41 C 0.1399(3) 0.6056(3) 0.2634(11) 0.214(5) Uani 1 1 d D . . . .
H41A H 0.143504 0.615467 0.371026 0.257 Uiso 1 1 calc R U . . .
H41B H 0.120035 0.652521 0.210501 0.257 Uiso 1 1 calc R U . . .
C42 C 0.2034(3) 0.5966(3) 0.2212(6) 0.1240(19) Uani 1 1 d D . . . .
H42A H 0.200909 0.596260 0.112343 0.149 Uiso 1 1 calc R U . . .
H42B H 0.228367 0.641940 0.262816 0.149 Uiso 1 1 calc R U . . .
C43 C 0.22656(18) 0.5212(4) 0.2840(7) 0.152(3) Uani 1 1 d D . . . .
H43A H 0.234766 0.526614 0.393160 0.183 Uiso 1 1 calc R U . . .
H43B H 0.263707 0.510989 0.250788 0.183 Uiso 1 1 calc R U . . .
C44 C 0.18848(17) 0.4500(2) 0.2451(5) 0.0933(12) Uani 1 1 d D . . . .
H44A H 0.184043 0.440897 0.137032 0.112 Uiso 1 1 calc R U . . .
H44B H 0.208108 0.402135 0.294976 0.112 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 N1 1.336(3) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(4) . ?
C3 H3 0.9500 . ?
C4 N1 1.380(3) . ?
C4 C5 1.411(3) . ?
C5 C6 1.401(3) . ?
C5 C10 1.479(3) . ?
C6 N2 1.385(3) . ?
C6 C7 1.429(3) . ?
C7 C8 1.350(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.421(3) . ?
C8 H8 0.9500 . ?
C9 N2 1.340(3) . ?
C9 C17 1.428(3) . ?
C10 C15 1.389(4) . ?
C10 C11 1.398(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C13 C16 1.505(4) . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N3 1.345(3) . ?
C17 C18 1.407(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.403(3) . ?
C19 H19 0.9500 . ?
C20 N3 1.370(3) . ?
C20 C21 1.422(3) . ?
C21 C22 1.384(3) . ?
C21 C26 1.487(3) . ?
C22 N4 1.410(3) . ?
C22 C23 1.424(3) . ?
C23 C24 1.355(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.418(4) . ?
C24 H24 0.9500 . ?
C25 N4 1.315(3) . ?
C25 H25 0.9500 . ?
C26 C31 1.390(3) . ?
C26 C27 1.392(3) . ?
C27 C28 1.384(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.390(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.395(3) . ?
C29 C32 1.498(3) . ?
C30 C31 1.379(3) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 O1 1.235(3) . ?
C32 N5 1.340(3) . ?
C33 C38 1.367(4) . ?
C33 C34 1.386(4) . ?
C33 N5 1.424(3) . ?
C34 C35 1.377(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.367(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.376(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.385(4) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
N1 H1A 0.8800 . ?
N3 H3A 0.8800 . ?
N5 H5 0.8800 . ?
C39 C44 1.338(5) . ?
C39 C40 1.533(6) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 C41 1.452(6) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.616(7) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.445(6) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.489(6) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?

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 109.1(3) . . ?
N1 C1 H1 125.4 . . ?
C2 C1 H1 125.4 . . ?
C3 C2 C1 107.2(3) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 107.9(3) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
N1 C4 C3 106.6(2) . . ?
N1 C4 C5 123.4(2) . . ?
C3 C4 C5 129.9(2) . . ?
C6 C5 C4 123.1(2) . . ?
C6 C5 C10 119.1(2) . . ?
C4 C5 C10 117.8(2) . . ?
N2 C6 C5 121.7(2) . . ?
N2 C6 C7 108.4(2) . . ?
C5 C6 C7 130.0(2) . . ?
C8 C7 C6 107.2(2) . . ?
C8 C7 H7 126.4 . . ?
C6 C7 H7 126.4 . . ?
C7 C8 C9 107.1(2) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.3(2) . . ?
N2 C9 C17 119.8(2) . . ?
C8 C9 C17 129.8(2) . . ?
C15 C10 C11 117.6(2) . . ?
C15 C10 C5 122.7(2) . . ?
C11 C10 C5 119.7(2) . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.9(3) . . ?
C11 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C14 117.2(3) . . ?
C12 C13 C16 120.2(3) . . ?
C14 C13 C16 122.6(3) . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C10 120.7(3) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 108.3(2) . . ?
N3 C17 C9 119.9(2) . . ?
C18 C17 C9 131.7(2) . . ?
C19 C18 C17 107.1(2) . . ?
C19 C18 H18 126.5 . . ?
C17 C18 H18 126.5 . . ?
C18 C19 C20 107.6(2) . . ?
C18 C19 H19 126.2 . . ?
C20 C19 H19 126.2 . . ?
N3 C20 C19 107.4(2) . . ?
N3 C20 C21 121.4(2) . . ?
C19 C20 C21 130.7(2) . . ?
C22 C21 C20 124.5(2) . . ?
C22 C21 C26 118.5(2) . . ?
C20 C21 C26 116.9(2) . . ?
C21 C22 N4 122.5(2) . . ?
C21 C22 C23 129.4(2) . . ?
N4 C22 C23 108.1(2) . . ?
C24 C23 C22 107.3(2) . . ?
C24 C23 H23 126.4 . . ?
C22 C23 H23 126.4 . . ?
C23 C24 C25 106.5(2) . . ?
C23 C24 H24 126.8 . . ?
C25 C24 H24 126.8 . . ?
N4 C25 C24 111.9(2) . . ?
N4 C25 H25 124.0 . . ?
C24 C25 H25 124.0 . . ?
C31 C26 C27 118.4(2) . . ?
C31 C26 C21 121.3(2) . . ?
C27 C26 C21 120.32(19) . . ?
C28 C27 C26 121.1(2) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 120.2(2) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C30 118.8(2) . . ?
C28 C29 C32 123.7(2) . . ?
C30 C29 C32 117.49(19) . . ?
C31 C30 C29 120.7(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C26 120.8(2) . . ?
C30 C31 H31 119.6 . . ?
C26 C31 H31 119.6 . . ?
O1 C32 N5 123.0(2) . . ?
O1 C32 C29 120.2(2) . . ?
N5 C32 C29 116.74(18) . . ?
C38 C33 C34 119.8(2) . . ?
C38 C33 N5 117.5(2) . . ?
C34 C33 N5 122.7(2) . . ?
C35 C34 C33 119.3(3) . . ?
C35 C34 H34 120.3 . . ?
C33 C34 H34 120.3 . . ?
C36 C35 C34 121.2(3) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 119.3(3) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C36 C37 C38 120.1(3) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C33 C38 C37 120.3(3) . . ?
C33 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C1 N1 C4 109.2(2) . . ?
C1 N1 H1A 125.4 . . ?
C4 N1 H1A 125.4 . . ?
C9 N2 C6 107.0(2) . . ?
C17 N3 C20 109.61(19) . . ?
C17 N3 H3A 125.2 . . ?
C20 N3 H3A 125.2 . . ?
C25 N4 C22 106.3(2) . . ?
C32 N5 C33 126.72(19) . . ?
C32 N5 H5 116.6 . . ?
C33 N5 H5 116.6 . . ?
C44 C39 C40 111.3(4) . . ?
C44 C39 H39A 109.4 . . ?
C40 C39 H39A 109.4 . . ?
C44 C39 H39B 109.4 . . ?
C40 C39 H39B 109.4 . . ?
H39A C39 H39B 108.0 . . ?
C41 C40 C39 114.5(4) . . ?
C41 C40 H40A 108.6 . . ?
C39 C40 H40A 108.6 . . ?
C41 C40 H40B 108.6 . . ?
C39 C40 H40B 108.6 . . ?
H40A C40 H40B 107.6 . . ?
C40 C41 C42 111.0(6) . . ?
C40 C41 H41A 109.4 . . ?
C42 C41 H41A 109.4 . . ?
C40 C41 H41B 109.4 . . ?
C42 C41 H41B 109.4 . . ?
H41A C41 H41B 108.0 . . ?
C43 C42 C41 106.6(4) . . ?
C43 C42 H42A 110.4 . . ?
C41 C42 H42A 110.4 . . ?
C43 C42 H42B 110.4 . . ?
C41 C42 H42B 110.4 . . ?
H42A C42 H42B 108.6 . . ?
C42 C43 C44 115.1(4) . . ?
C42 C43 H43A 108.5 . . ?
C44 C43 H43A 108.5 . . ?
C42 C43 H43B 108.5 . . ?
C44 C43 H43B 108.5 . . ?
H43A C43 H43B 107.5 . . ?
C39 C44 C43 115.8(4) . . ?
C39 C44 H44A 108.3 . . ?
C43 C44 H44A 108.3 . . ?
C39 C44 H44B 108.3 . . ?
C43 C44 H44B 108.3 . . ?
H44A C44 H44B 107.4 . . ?

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_compound9
_database_code_depnum_ccdc_archive 'CCDC 1817913'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 N4 Ni O2'
_chemical_formula_weight         567.27

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'
Ni Ni 0.3393 1.1124 '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                   10.4334(4)
_cell_length_b                   11.4214(4)
_cell_length_c                   12.7442(5)
_cell_angle_alpha                64.165(2)
_cell_angle_beta                 78.961(2)
_cell_angle_gamma                71.119(2)
_cell_volume                     1291.05(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6385
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.52

_exptl_crystal_description       plate
_exptl_crystal_colour            red-brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.791
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.983
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17194
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.059
_diffrn_reflns_theta_max         30.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             6986
_reflns_number_gt                4202
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1020P)²+0.6607P] 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         6986
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1298
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.2015
_refine_ls_wR_factor_gt          0.1725
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_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 0.4790(5) -0.1451(5) 0.6610(4) 0.0434(11) Uani 1 1 d . . . . .
H1 H 0.525527 -0.094749 0.593041 0.052 Uiso 1 1 calc R U . . .
C2 C 0.4316(5) -0.2493(5) 0.6697(4) 0.0508(12) Uani 1 1 d . . . . .
H2 H 0.441449 -0.283451 0.611821 0.061 Uiso 1 1 calc R U . . .
C3 C 0.3677(5) -0.2933(4) 0.7784(4) 0.0417(10) Uani 1 1 d . . . . .
H3 H 0.324967 -0.364526 0.810511 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3771(4) -0.2129(4) 0.8342(4) 0.0327(9) Uani 1 1 d . . . . .
C5 C 0.3039(4) -0.2067(4) 0.9376(3) 0.0307(8) Uani 1 1 d . . . . .
C6 C 0.2923(4) -0.1023(4) 0.9703(3) 0.0314(8) Uani 1 1 d . . . . .
C7 C 0.2172(4) -0.0698(4) 1.0651(4) 0.0359(9) Uani 1 1 d . . . . .
H7 H 0.162815 -0.120592 1.124972 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2380(4) 0.0480(4) 1.0539(4) 0.0348(9) Uani 1 1 d . . . . .
H8 H 0.201021 0.093955 1.104183 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3249(4) 0.0876(4) 0.9532(4) 0.0322(9) Uani 1 1 d . . . . .
C10 C 0.2278(4) -0.3092(4) 1.0072(3) 0.0312(8) Uani 1 1 d . . . . .
C11 C 0.2916(4) -0.4469(4) 1.0510(3) 0.0345(9) Uani 1 1 d . . . . .
H11 H 0.387167 -0.477130 1.038546 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2186(4) -0.5408(4) 1.1123(4) 0.0382(9) Uani 1 1 d . . . . .
H12 H 0.264809 -0.634441 1.141832 0.046 Uiso 1 1 calc R U . . .
C13 C 0.0792(4) -0.5004(4) 1.1313(4) 0.0376(9) Uani 1 1 d . . . . .
C14 C 0.0158(4) -0.3630(4) 1.0901(4) 0.0415(10) Uani 1 1 d . . . . .
H14 H -0.079430 -0.333105 1.104205 0.050 Uiso 1 1 calc R U . . .
C15 C 0.0880(4) -0.2687(4) 1.0289(4) 0.0385(10) Uani 1 1 d . . . . .
H15 H 0.041770 -0.175085 1.001256 0.046 Uiso 1 1 calc R U . . .
C16 C -0.0045(5) -0.6004(5) 1.1960(4) 0.0541(13) Uani 1 1 d . . . . .
H16A H -0.015594 -0.616885 1.278992 0.081 Uiso 1 1 calc R U . . .
H16B H 0.041732 -0.685589 1.187459 0.081 Uiso 1 1 calc R U . . .
H16C H -0.093923 -0.563329 1.163492 0.081 Uiso 1 1 calc R U . . .
C17 C 0.7281(4) -0.0482(5) 0.6385(5) 0.0493(12) Uani 1 1 d . . . . .
H17 H 0.722178 -0.137285 0.660584 0.059 Uiso 1 1 calc R U . . .
C18 C 0.8321(5) 0.0022(5) 0.5661(5) 0.0576(14) Uani 1 1 d . . . . .
H18 H 0.907174 -0.044278 0.530717 0.069 Uiso 1 1 calc R U . . .
C19 C 0.8057(4) 0.1318(5) 0.5557(4) 0.0475(12) Uani 1 1 d . . . . .
H19 H 0.858222 0.193221 0.510067 0.057 Uiso 1 1 calc R U . . .
C20 C 0.6855(4) 0.1580(4) 0.6252(4) 0.0355(9) Uani 1 1 d . . . . .
C21 C 0.6362(4) 0.2686(4) 0.6564(3) 0.0305(8) Uani 1 1 d . . . . .
C22 C 0.5384(4) 0.2714(4) 0.7467(4) 0.0306(8) Uani 1 1 d . . . . .
C23 C 0.4820(4) 0.3668(4) 0.7978(4) 0.0348(9) Uani 1 1 d . . . . .
H23 H 0.503122 0.449951 0.774222 0.042 Uiso 1 1 calc R U . . .
C24 C 0.3921(4) 0.3177(4) 0.8870(4) 0.0365(9) Uani 1 1 d . . . . .
H24 H 0.338960 0.359778 0.936956 0.044 Uiso 1 1 calc R U . . .
C25 C 0.3937(4) 0.1917(4) 0.8902(4) 0.0334(9) Uani 1 1 d . . . . .
C26 C 0.6982(4) 0.3836(4) 0.5959(4) 0.0322(8) Uani 1 1 d . . . . .
C27 C 0.6934(4) 0.4575(4) 0.4763(4) 0.0380(9) Uani 1 1 d . . . . .
H27 H 0.651546 0.433065 0.431728 0.046 Uiso 1 1 calc R U . . .
C28 C 0.7480(4) 0.5656(4) 0.4208(4) 0.0390(10) Uani 1 1 d . . . . .
H28 H 0.743901 0.614954 0.338663 0.047 Uiso 1 1 calc R U . . .
C29 C 0.8095(4) 0.6028(4) 0.4850(4) 0.0366(9) Uani 1 1 d . . . . .
C30 C 0.8154(4) 0.5283(5) 0.6035(4) 0.0433(10) Uani 1 1 d . . . . .
H30 H 0.858088 0.552193 0.647898 0.052 Uiso 1 1 calc R U . . .
C31 C 0.7609(4) 0.4201(4) 0.6594(4) 0.0395(10) Uani 1 1 d . . . . .
H31 H 0.766098 0.370318 0.741441 0.047 Uiso 1 1 calc R U . . .
C32 C 0.8673(4) 0.7166(5) 0.4338(4) 0.0423(10) Uani 1 1 d . . . . .
C33 C 0.9080(6) 0.8996(6) 0.2680(5) 0.0752(18) Uani 1 1 d . . . . .
H33A H 0.842610 0.973608 0.285405 0.113 Uiso 1 1 calc R U . . .
H33B H 0.919241 0.926141 0.183334 0.113 Uiso 1 1 calc R U . . .
H33C H 0.995544 0.879836 0.298360 0.113 Uiso 1 1 calc R U . . .
N1 N 0.4521(3) -0.1233(3) 0.7588(3) 0.0340(7) Uani 1 1 d . . . . .
N2 N 0.3567(3) -0.0032(3) 0.9040(3) 0.0311(7) Uani 1 1 d . . . . .
N3 N 0.4814(3) 0.1654(3) 0.8055(3) 0.0295(7) Uani 1 1 d . . . . .
N4 N 0.6363(3) 0.0434(3) 0.6738(3) 0.0365(8) Uani 1 1 d . . . . .
O1 O 0.9201(4) 0.7482(4) 0.4927(3) 0.0696(11) Uani 1 1 d . . . . .
O2 O 0.8585(4) 0.7802(4) 0.3228(3) 0.0618(10) Uani 1 1 d . . . . .
Ni1 Ni 0.48571(5) 0.01677(5) 0.78114(4) 0.02933(18) 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 1.336(5) . ?
C1 C2 1.385(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.368(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.420(5) . ?
C3 H3 0.9500 . ?
C4 N1 1.398(5) . ?
C4 C5 1.408(5) . ?
C5 C6 1.390(5) . ?
C5 C10 1.488(5) . ?
C6 N2 1.374(5) . ?
C6 C7 1.432(5) . ?
C7 C8 1.374(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(5) . ?
C8 H8 0.9500 . ?
C9 N2 1.357(5) . ?
C9 C25 1.440(6) . ?
C10 C11 1.389(5) . ?
C10 C15 1.392(5) . ?
C11 C12 1.383(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(6) . ?
C13 C16 1.516(6) . ?
C14 C15 1.380(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N4 1.346(5) . ?
C17 C18 1.385(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.364(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.418(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(5) . ?
C20 N4 1.403(5) . ?
C21 C22 1.388(5) . ?
C21 C26 1.488(5) . ?
C22 N3 1.373(5) . ?
C22 C23 1.420(5) . ?
C23 C24 1.364(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.417(5) . ?
C24 H24 0.9500 . ?
C25 N3 1.348(5) . ?
C26 C27 1.385(6) . ?
C26 C31 1.390(5) . ?
C27 C28 1.374(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.394(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.375(6) . ?
C29 C32 1.448(6) . ?
C30 C31 1.375(6) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 O1 1.233(5) . ?
C32 O2 1.284(6) . ?
C33 O2 1.450(6) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
N1 Ni1 1.888(3) . ?
N2 Ni1 1.843(3) . ?
N3 Ni1 1.841(3) . ?
N4 Ni1 1.885(3) . ?

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 112.5(4) . . ?
N1 C1 H1 123.7 . . ?
C2 C1 H1 123.7 . . ?
C3 C2 C1 106.3(4) . . ?
C3 C2 H2 126.9 . . ?
C1 C2 H2 126.9 . . ?
C2 C3 C4 107.3(4) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C5 125.1(3) . . ?
N1 C4 C3 108.1(3) . . ?
C5 C4 C3 125.9(4) . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 C10 119.7(3) . . ?
C4 C5 C10 118.2(3) . . ?
N2 C6 C5 120.5(3) . . ?
N2 C6 C7 107.5(3) . . ?
C5 C6 C7 131.9(4) . . ?
C8 C7 C6 107.7(4) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 C9 106.7(3) . . ?
C7 C8 H8 126.7 . . ?
C9 C8 H8 126.7 . . ?
N2 C9 C8 109.8(3) . . ?
N2 C9 C25 111.2(3) . . ?
C8 C9 C25 139.0(4) . . ?
C11 C10 C15 117.8(4) . . ?
C11 C10 C5 122.0(3) . . ?
C15 C10 C5 120.3(4) . . ?
C12 C11 C10 121.2(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 117.9(4) . . ?
C12 C13 C16 122.4(4) . . ?
C14 C13 C16 119.6(4) . . ?
C15 C14 C13 121.4(4) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C10 120.7(4) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 C18 112.3(4) . . ?
N4 C17 H17 123.8 . . ?
C18 C17 H17 123.8 . . ?
C19 C18 C17 106.5(4) . . ?
C19 C18 H18 126.8 . . ?
C17 C18 H18 126.8 . . ?
C18 C19 C20 107.6(4) . . ?
C18 C19 H19 126.2 . . ?
C20 C19 H19 126.2 . . ?
C21 C20 N4 124.8(4) . . ?
C21 C20 C19 126.2(4) . . ?
N4 C20 C19 108.2(3) . . ?
C22 C21 C20 122.7(4) . . ?
C22 C21 C26 118.7(3) . . ?
C20 C21 C26 118.5(4) . . ?
N3 C22 C21 120.0(3) . . ?
N3 C22 C23 108.1(3) . . ?
C21 C22 C23 131.9(4) . . ?
C24 C23 C22 107.8(4) . . ?
C24 C23 H23 126.1 . . ?
C22 C23 H23 126.1 . . ?
C23 C24 C25 106.4(3) . . ?
C23 C24 H24 126.8 . . ?
C25 C24 H24 126.8 . . ?
N3 C25 C24 109.9(4) . . ?
N3 C25 C9 111.3(3) . . ?
C24 C25 C9 138.7(4) . . ?
C27 C26 C31 118.6(4) . . ?
C27 C26 C21 121.3(3) . . ?
C31 C26 C21 120.1(4) . . ?
C28 C27 C26 121.2(4) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C29 120.0(4) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 118.6(4) . . ?
C30 C29 C32 117.9(4) . . ?
C28 C29 C32 123.5(4) . . ?
C31 C30 C29 121.6(4) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C31 C26 120.0(4) . . ?
C30 C31 H31 120.0 . . ?
C26 C31 H31 120.0 . . ?
O1 C32 O2 123.7(4) . . ?
O1 C32 C29 122.3(4) . . ?
O2 C32 C29 114.0(4) . . ?
O2 C33 H33A 109.5 . . ?
O2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C1 N1 C4 105.7(3) . . ?
C1 N1 Ni1 126.6(3) . . ?
C4 N1 Ni1 127.1(3) . . ?
C9 N2 C6 108.3(3) . . ?
C9 N2 Ni1 117.3(3) . . ?
C6 N2 Ni1 133.8(3) . . ?
C25 N3 C22 107.8(3) . . ?
C25 N3 Ni1 117.7(3) . . ?
C22 N3 Ni1 134.0(3) . . ?
C17 N4 C20 105.3(3) . . ?
C17 N4 Ni1 127.5(3) . . ?
C20 N4 Ni1 126.8(3) . . ?
C32 O2 C33 116.2(4) . . ?
N3 Ni1 N2 82.24(14) . . ?
N3 Ni1 N4 89.79(13) . . ?
N2 Ni1 N4 168.68(14) . . ?
N3 Ni1 N1 168.55(13) . . ?
N2 Ni1 N1 89.68(14) . . ?
N4 Ni1 N1 99.29(14) . . ?

_refine_diff_density_max         1.512
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_compound16cis
_database_code_depnum_ccdc_archive 'CCDC 1817916'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C76 H54 N10 O2 Zn2'
_chemical_formula_weight         1270.03

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/n'
_space_group_name_Hall           '-P 2yac'

_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+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   21.6164(17)
_cell_length_b                   9.6459(5)
_cell_length_c                   33.206(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.0870(10)
_cell_angle_gamma                90
_cell_volume                     6913.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6591
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.27

_exptl_crystal_description       platelet
_exptl_crystal_colour            dark-purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_F_000             2624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.746
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.984
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58115
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         30.063
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             19878
_reflns_number_gt                8821
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0928P)²+1.8416P] 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         19878
_refine_ls_number_parameters     807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1796
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2170
_refine_ls_wR_factor_gt          0.1770
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_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 0.2313(2) 0.5241(5) 0.61244(16) 0.0632(13) Uani 1 1 d . . . . .
H1 H 0.193971 0.574971 0.614693 0.076 Uiso 1 1 calc R U . . .
C2 C 0.2861(2) 0.5806(5) 0.59825(16) 0.0642(14) Uani 1 1 d . . . . .
H2 H 0.292104 0.672438 0.588895 0.077 Uiso 1 1 calc R U . . .
C3 C 0.32868(19) 0.4772(4) 0.60066(14) 0.0516(11) Uani 1 1 d . . . . .
H3 H 0.370621 0.483751 0.593679 0.062 Uiso 1 1 calc R U . . .
C4 C 0.29943(17) 0.3578(4) 0.61543(13) 0.0452(10) Uani 1 1 d . . . . .
C5 C 0.32500(17) 0.2242(4) 0.62185(13) 0.0433(10) Uani 1 1 d . . . . .
C6 C 0.29287(17) 0.1044(4) 0.63017(13) 0.0451(10) Uani 1 1 d . . . . .
C7 C 0.31954(18) -0.0251(4) 0.64321(14) 0.0516(11) Uani 1 1 d . . . . .
H7 H 0.362495 -0.045832 0.646327 0.062 Uiso 1 1 calc R U . . .
C8 C 0.27187(18) -0.1133(5) 0.65035(15) 0.0544(12) Uani 1 1 d . . . . .
H8 H 0.275180 -0.205981 0.659892 0.065 Uiso 1 1 calc R U . . .
C9 C 0.21650(18) -0.0389(4) 0.64068(14) 0.0508(11) Uani 1 1 d . . . . .
C10 C 0.15439(18) -0.0926(5) 0.64070(14) 0.0532(12) Uani 1 1 d . . . . .
C11 C 0.1319(2) -0.2024(5) 0.66339(16) 0.0659(14) Uani 1 1 d . . . . .
H11 H 0.155488 -0.259815 0.681700 0.079 Uiso 1 1 calc R U . . .
C12 C 0.0695(2) -0.2113(5) 0.65412(16) 0.0697(15) Uani 1 1 d . . . . .
H12 H 0.041638 -0.275719 0.665029 0.084 Uiso 1 1 calc R U . . .
C13 C 0.05386(18) -0.1060(5) 0.62508(15) 0.0549(12) Uani 1 1 d . . . . .
C14 C -0.00460(18) -0.0790(5) 0.60639(14) 0.0547(12) Uani 1 1 d . . . . .
C15 C -0.01752(18) 0.0083(5) 0.57369(14) 0.0511(11) Uani 1 1 d . . . . .
C16 C -0.07647(19) 0.0522(5) 0.55684(15) 0.0580(13) Uani 1 1 d . . . . .
H16 H -0.115749 0.023150 0.565234 0.070 Uiso 1 1 calc R U . . .
C17 C -0.0663(2) 0.1429(5) 0.52664(16) 0.0635(13) Uani 1 1 d . . . . .
H17 H -0.096738 0.190498 0.510246 0.076 Uiso 1 1 calc R U . . .
C18 C -0.0025(2) 0.1523(5) 0.52449(15) 0.0580(12) Uani 1 1 d . . . . .
H18 H 0.017397 0.208308 0.505513 0.070 Uiso 1 1 calc R U . . .
C19 C 0.39412(18) 0.2150(4) 0.61988(15) 0.0482(11) Uani 1 1 d . . . . .
C20 C 0.4204(2) 0.1192(5) 0.59481(18) 0.0679(15) Uani 1 1 d . . . . .
H20 H 0.394598 0.063134 0.577408 0.082 Uiso 1 1 calc R U . . .
C21 C 0.4839(2) 0.1049(5) 0.5950(2) 0.0789(18) Uani 1 1 d . . . . .
H21 H 0.501417 0.035540 0.578818 0.095 Uiso 1 1 calc R U . . .
C22 C 0.5223(2) 0.1901(5) 0.61849(19) 0.0674(15) Uani 1 1 d . . . . .
C23 C 0.49662(18) 0.2868(4) 0.64373(15) 0.0524(12) Uani 1 1 d . . . . .
H23 H 0.522589 0.344720 0.660472 0.063 Uiso 1 1 calc R U . . .
C24 C 0.43249(18) 0.2979(4) 0.64423(14) 0.0473(11) Uani 1 1 d . . . . .
H24 H 0.414806 0.363571 0.661574 0.057 Uiso 1 1 calc R U . . .
C25 C 0.5907(2) 0.1650(5) 0.6184(2) 0.0803(19) Uani 1 1 d . . . . .
C26 C 0.69360(19) 0.2629(5) 0.61882(17) 0.0600(13) Uani 1 1 d . . . . .
C27 C 0.7243(2) 0.3320(7) 0.5926(2) 0.103(2) Uani 1 1 d . . . . .
H27 H 0.702400 0.392153 0.574147 0.124 Uiso 1 1 calc R U . . .
C28 C 0.7890(3) 0.3194(9) 0.5909(3) 0.136(3) Uani 1 1 d . . . . .
H28 H 0.810232 0.370184 0.571430 0.164 Uiso 1 1 calc R U . . .
C29 C 0.8201(3) 0.2379(9) 0.6162(3) 0.107(3) Uani 1 1 d . . . . .
H29 H 0.863820 0.231854 0.615224 0.128 Uiso 1 1 calc R U . . .
C30 C 0.7905(3) 0.1614(9) 0.6440(3) 0.119(3) Uani 1 1 d . . . . .
H30 H 0.813155 0.101142 0.661972 0.142 Uiso 1 1 calc R U . . .
C31 C 0.7260(3) 0.1736(7) 0.6454(2) 0.106(2) Uani 1 1 d . . . . .
H31 H 0.704413 0.121381 0.664485 0.127 Uiso 1 1 calc R U . . .
C32 C -0.05817(19) -0.1547(5) 0.62288(15) 0.0603(13) Uani 1 1 d . . . . .
C33 C -0.0692(2) -0.1418(7) 0.66377(18) 0.0846(18) Uani 1 1 d . . . . .
H33 H -0.043626 -0.083939 0.680785 0.102 Uiso 1 1 calc R U . . .
C34 C -0.1183(3) -0.2149(8) 0.6794(2) 0.104(2) Uani 1 1 d . . . . .
H34 H -0.125597 -0.207426 0.707243 0.125 Uiso 1 1 calc R U . . .
C35 C -0.1565(2) -0.2979(8) 0.6549(2) 0.101(2) Uani 1 1 d . . . . .
C36 C -0.1453(2) -0.3093(6) 0.61527(19) 0.0788(18) Uani 1 1 d . . . . .
H36 H -0.171045 -0.367364 0.598418 0.095 Uiso 1 1 calc R U . . .
C37 C -0.09694(19) -0.2374(5) 0.59883(17) 0.0642(14) Uani 1 1 d . . . . .
H37 H -0.090527 -0.245323 0.570846 0.077 Uiso 1 1 calc R U . . .
C38 C -0.2091(3) -0.3794(10) 0.6731(2) 0.147(4) Uani 1 1 d . . . . .
H38A H -0.217313 -0.340904 0.699569 0.220 Uiso 1 1 calc R U . . .
H38B H -0.197050 -0.476967 0.676051 0.220 Uiso 1 1 calc R U . . .
H38C H -0.246565 -0.372440 0.655217 0.220 Uiso 1 1 calc R U . . .
C39 C 0.1792(2) 0.1440(7) 0.72161(17) 0.087(2) Uani 1 1 d . . . . .
H39 H 0.219207 0.105731 0.718767 0.104 Uiso 1 1 calc R U . . .
C40 C 0.1455(2) 0.1282(7) 0.75631(17) 0.0854(19) Uani 1 1 d . . . . .
H40 H 0.158305 0.080794 0.780409 0.102 Uiso 1 1 calc R U . . .
C41 C 0.0907(2) 0.1949(6) 0.74831(15) 0.0660(14) Uani 1 1 d . . . . .
H41 H 0.057450 0.201433 0.765800 0.079 Uiso 1 1 calc R U . . .
C42 C 0.09229(18) 0.2528(5) 0.70902(14) 0.0564(12) Uani 1 1 d . . . . .
C43 C 0.04521(17) 0.3253(5) 0.68769(14) 0.0477(11) Uani 1 1 d . . . . .
C44 C 0.04451(17) 0.3648(4) 0.64722(14) 0.0474(10) Uani 1 1 d . . . . .
C45 C -0.0004(2) 0.4500(5) 0.62585(16) 0.0596(13) Uani 1 1 d . . . . .
H45 H -0.037006 0.486669 0.636343 0.072 Uiso 1 1 calc R U . . .
C46 C 0.0184(2) 0.4690(5) 0.58818(16) 0.0631(14) Uani 1 1 d . . . . .
H46 H -0.001954 0.522323 0.567384 0.076 Uiso 1 1 calc R U . . .
C47 C 0.0747(2) 0.3937(5) 0.58564(14) 0.0527(11) Uani 1 1 d . . . . .
C48 C 0.11302(19) 0.3746(5) 0.55188(14) 0.0497(11) Uani 1 1 d . . . . .
C49 C 0.1274(2) 0.4686(5) 0.52111(15) 0.0608(13) Uani 1 1 d . . . . .
H49 H 0.109363 0.557426 0.516415 0.073 Uiso 1 1 calc R U . . .
C50 C 0.1715(2) 0.4087(5) 0.49960(15) 0.0618(13) Uani 1 1 d . . . . .
H50 H 0.191093 0.448924 0.477499 0.074 Uiso 1 1 calc R U . . .
C51 C 0.18333(19) 0.2741(4) 0.51605(13) 0.0476(10) Uani 1 1 d . . . . .
C52 C 0.22262(18) 0.1718(4) 0.50113(13) 0.0469(11) Uani 1 1 d . . . . .
C53 C 0.22406(18) 0.0322(5) 0.51195(14) 0.0529(12) Uani 1 1 d . . . . .
C54 C 0.2658(2) -0.0720(5) 0.49976(16) 0.0696(15) Uani 1 1 d . . . . .
H54 H 0.298396 -0.059887 0.482006 0.083 Uiso 1 1 calc R U . . .
C55 C 0.2503(2) -0.1927(6) 0.51830(18) 0.0798(17) Uani 1 1 d . . . . .
H55 H 0.270155 -0.280086 0.516216 0.096 Uiso 1 1 calc R U . . .
C56 C 0.1999(2) -0.1621(5) 0.54073(16) 0.0628(13) Uani 1 1 d . . . . .
H56 H 0.179674 -0.227945 0.556750 0.075 Uiso 1 1 calc R U . . .
C57 C 0.26711(18) 0.2167(4) 0.47089(14) 0.0462(10) Uani 1 1 d . . . . .
C58 C 0.3092(2) 0.3219(5) 0.48043(15) 0.0586(12) Uani 1 1 d . . . . .
H58 H 0.307670 0.368860 0.505505 0.070 Uiso 1 1 calc R U . . .
C59 C 0.3534(2) 0.3591(5) 0.45366(15) 0.0587(12) Uani 1 1 d . . . . .
H59 H 0.382329 0.430532 0.460533 0.070 Uiso 1 1 calc R U . . .
C60 C 0.35527(18) 0.2918(4) 0.41679(14) 0.0468(10) Uani 1 1 d . . . . .
C61 C 0.31194(18) 0.1912(4) 0.40674(13) 0.0447(10) Uani 1 1 d . . . . .
H61 H 0.311920 0.147062 0.381164 0.054 Uiso 1 1 calc R U . . .
C62 C 0.26878(18) 0.1546(4) 0.43368(14) 0.0479(11) Uani 1 1 d . . . . .
H62 H 0.239314 0.084631 0.426439 0.057 Uiso 1 1 calc R U . . .
C63 C 0.40633(19) 0.3320(5) 0.38981(14) 0.0492(11) Uani 1 1 d . . . . .
C64 C 0.5280(2) 0.3206(5) 0.34774(15) 0.0592(13) Uani 1 1 d . . . . .
H64 H 0.529682 0.386114 0.369129 0.071 Uiso 1 1 calc R U . . .
C65 C 0.5749(2) 0.3165(5) 0.32040(17) 0.0675(14) Uani 1 1 d . . . . .
H65 H 0.608524 0.379888 0.323383 0.081 Uiso 1 1 calc R U . . .
C66 C 0.5734(3) 0.2237(6) 0.28969(18) 0.0751(16) Uani 1 1 d . . . . .
H66 H 0.605417 0.222306 0.271216 0.090 Uiso 1 1 calc R U . . .
C67 C 0.5244(3) 0.1308(6) 0.28553(19) 0.0888(19) Uani 1 1 d . . . . .
H67 H 0.523049 0.065645 0.264046 0.107 Uiso 1 1 calc R U . . .
C68 C 0.4777(2) 0.1319(5) 0.31218(19) 0.0784(17) Uani 1 1 d . . . . .
H68 H 0.444544 0.067324 0.309326 0.094 Uiso 1 1 calc R U . . .
C69 C 0.4795(2) 0.2288(5) 0.34336(16) 0.0564(12) Uani 1 1 d . . . . .
C70 C -0.00909(18) 0.3662(5) 0.71120(13) 0.0527(11) Uani 1 1 d . . . . .
C71 C -0.0052(2) 0.4715(6) 0.73778(19) 0.0859(18) Uani 1 1 d . . . . .
H71 H 0.032389 0.522220 0.741165 0.103 Uiso 1 1 calc R U . . .
C72 C -0.0549(3) 0.5074(7) 0.76033(19) 0.095(2) Uani 1 1 d . . . . .
H72 H -0.050625 0.582920 0.778643 0.114 Uiso 1 1 calc R U . . .
C73 C -0.1085(2) 0.4387(7) 0.75699(17) 0.0816(18) Uani 1 1 d . . . . .
C74 C -0.1147(3) 0.3373(9) 0.7286(3) 0.139(4) Uani 1 1 d . . . . .
H74 H -0.153352 0.291732 0.723764 0.166 Uiso 1 1 calc R U . . .
C75 C -0.0641(3) 0.3004(8) 0.7066(2) 0.121(3) Uani 1 1 d . . . . .
H75 H -0.068449 0.226504 0.687747 0.145 Uiso 1 1 calc R U . . .
C76 C -0.1631(3) 0.4763(9) 0.78254(19) 0.116(3) Uani 1 1 d . . . . .
H76A H -0.148105 0.490318 0.810613 0.173 Uiso 1 1 calc R U . . .
H76B H -0.193522 0.400777 0.781190 0.173 Uiso 1 1 calc R U . . .
H76C H -0.182666 0.561653 0.772138 0.173 Uiso 1 1 calc R U . . .
N1 N 0.23796(15) 0.3907(4) 0.62234(11) 0.0513(9) Uani 1 1 d . . . . .
N2 N 0.22888(13) 0.0919(3) 0.62913(11) 0.0442(9) Uani 1 1 d . . . . .
N3 N 0.10725(14) -0.0317(4) 0.61723(11) 0.0491(9) Uani 1 1 d . . . . .
N4 N 0.02751(15) 0.0741(4) 0.55199(11) 0.0504(9) Uani 1 1 d . . . . .
N5 N 0.62773(18) 0.2756(4) 0.6195(2) 0.1026(13) Uani 1 1 d . . . . .
H5 H 0.611185 0.358791 0.620580 0.123 Uiso 1 1 calc R U . . .
N6 N 0.14906(16) 0.2181(5) 0.69328(12) 0.0663(12) Uani 1 1 d . . . . .
N7 N 0.09003(14) 0.3305(4) 0.62082(11) 0.0475(9) Uani 1 1 d . . . . .
N8 N 0.14601(15) 0.2574(3) 0.54844(11) 0.0472(9) Uani 1 1 d . . . . .
N9 N 0.18313(14) -0.0301(4) 0.53725(12) 0.0511(9) Uani 1 1 d . . . . .
N10 N 0.43056(17) 0.2232(4) 0.37047(12) 0.0574(10) Uani 1 1 d . . . . .
H10 H 0.414649 0.141034 0.375027 0.069 Uiso 1 1 calc R U . . .
O1 O 0.61097(14) 0.0481(3) 0.61640(16) 0.1026(13) Uani 1 1 d . . . . .
O2 O 0.42416(14) 0.4515(3) 0.38658(10) 0.0613(9) Uani 1 1 d . . . . .
Zn1 Zn 0.17389(2) 0.25647(5) 0.63796(2) 0.04945(16) Uani 1 1 d . . . . .
Zn2 Zn 0.11771(2) 0.06909(5) 0.56604(2) 0.04936(16) 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 1.334(6) . ?
C1 C2 1.409(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.356(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(6) . ?
C3 H3 0.9500 . ?
C4 N1 1.397(5) . ?
C4 C5 1.413(5) . ?
C5 C6 1.384(5) . ?
C5 C19 1.502(5) . ?
C6 N2 1.387(5) . ?
C6 C7 1.433(6) . ?
C7 C8 1.367(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.418(6) . ?
C8 H8 0.9500 . ?
C9 N2 1.350(5) . ?
C9 C10 1.439(5) . ?
C10 N3 1.380(5) . ?
C10 C11 1.402(6) . ?
C11 C12 1.371(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.428(6) . ?
C12 H12 0.9500 . ?
C13 N3 1.395(5) . ?
C13 C14 1.402(6) . ?
C14 C15 1.391(6) . ?
C14 C32 1.497(6) . ?
C15 N4 1.395(5) . ?
C15 C16 1.428(6) . ?
C16 C17 1.358(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(6) . ?
C17 H17 0.9500 . ?
C18 N4 1.326(5) . ?
C18 H18 0.9500 . ?
C19 C24 1.382(6) . ?
C19 C20 1.386(6) . ?
C20 C21 1.379(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.379(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(7) . ?
C22 C25 1.499(6) . ?
C23 C24 1.391(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 O1 1.213(5) . ?
C25 N5 1.334(6) . ?
C26 C27 1.306(7) . ?
C26 C31 1.395(8) . ?
C26 N5 1.431(5) . ?
C27 C28 1.410(8) . ?
C27 H27 0.9500 . ?
C28 C29 1.307(10) . ?
C28 H28 0.9500 . ?
C29 C30 1.367(10) . ?
C29 H29 0.9500 . ?
C30 C31 1.403(8) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C37 1.380(7) . ?
C32 C33 1.397(7) . ?
C33 C34 1.397(7) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(10) . ?
C34 H34 0.9500 . ?
C35 C36 1.355(9) . ?
C35 C38 1.534(7) . ?
C36 C37 1.391(6) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 N6 1.324(6) . ?
C39 C40 1.404(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.361(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.422(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.396(6) . ?
C42 N6 1.400(5) . ?
C43 C44 1.396(6) . ?
C43 C70 1.497(5) . ?
C44 N7 1.392(5) . ?
C44 C45 1.431(6) . ?
C45 C46 1.348(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.423(6) . ?
C46 H46 0.9500 . ?
C47 N7 1.344(5) . ?
C47 C48 1.441(6) . ?
C48 N8 1.345(5) . ?
C48 C49 1.413(6) . ?
C49 C50 1.352(6) . ?
C49 H49 0.9500 . ?
C50 C51 1.426(6) . ?
C50 H50 0.9500 . ?
C51 N8 1.388(5) . ?
C51 C52 1.409(6) . ?
C52 C53 1.394(6) . ?
C52 C57 1.492(5) . ?
C53 N9 1.389(5) . ?
C53 C54 1.424(6) . ?
C54 C55 1.367(7) . ?
C54 H54 0.9500 . ?
C55 C56 1.384(7) . ?
C55 H55 0.9500 . ?
C56 N9 1.327(5) . ?
C56 H56 0.9500 . ?
C57 C62 1.375(6) . ?
C57 C58 1.388(6) . ?
C58 C59 1.387(6) . ?
C58 H58 0.9500 . ?
C59 C60 1.388(6) . ?
C59 H59 0.9500 . ?
C60 C61 1.377(6) . ?
C60 C63 1.509(6) . ?
C61 C62 1.373(5) . ?
C61 H61 0.9500 . ?
C62 H62 0.9500 . ?
C63 O2 1.222(5) . ?
C63 N10 1.351(5) . ?
C64 C69 1.375(6) . ?
C64 C65 1.397(6) . ?
C64 H64 0.9500 . ?
C65 C66 1.356(8) . ?
C65 H65 0.9500 . ?
C66 C67 1.388(8) . ?
C66 H66 0.9500 . ?
C67 C68 1.378(7) . ?
C67 H67 0.9500 . ?
C68 C69 1.393(7) . ?
C68 H68 0.9500 . ?
C69 N10 1.427(5) . ?
C70 C71 1.345(7) . ?
C70 C75 1.349(7) . ?
C71 C72 1.386(7) . ?
C71 H71 0.9500 . ?
C72 C73 1.335(8) . ?
C72 H72 0.9500 . ?
C73 C74 1.361(9) . ?
C73 C76 1.534(7) . ?
C74 C75 1.394(7) . ?
C74 H74 0.9500 . ?
C75 H75 0.9500 . ?
C76 H76A 0.9800 . ?
C76 H76B 0.9800 . ?
C76 H76C 0.9800 . ?
N1 Zn1 1.985(3) . ?
N2 Zn1 2.014(3) . ?
N3 Zn2 1.982(3) . ?
N4 Zn2 1.981(3) . ?
N5 H5 0.8800 . ?
N6 Zn1 1.976(4) . ?
N7 Zn1 2.002(3) . ?
N8 Zn2 2.013(3) . ?
N9 Zn2 1.994(3) . ?
N10 H10 0.8800 . ?

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 111.9(4) . . ?
N1 C1 H1 124.0 . . ?
C2 C1 H1 124.0 . . ?
C3 C2 C1 106.0(4) . . ?
C3 C2 H2 127.0 . . ?
C1 C2 H2 127.0 . . ?
C2 C3 C4 107.8(4) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C5 123.4(3) . . ?
N1 C4 C3 108.6(3) . . ?
C5 C4 C3 128.0(3) . . ?
C6 C5 C4 126.5(3) . . ?
C6 C5 C19 118.0(3) . . ?
C4 C5 C19 115.4(3) . . ?
C5 C6 N2 125.3(3) . . ?
C5 C6 C7 126.2(3) . . ?
N2 C6 C7 108.4(3) . . ?
C8 C7 C6 107.5(3) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.3(4) . . ?
C7 C8 H8 126.9 . . ?
C9 C8 H8 126.9 . . ?
N2 C9 C8 111.1(3) . . ?
N2 C9 C10 122.4(4) . . ?
C8 C9 C10 126.4(4) . . ?
N3 C10 C11 111.0(4) . . ?
N3 C10 C9 120.5(4) . . ?
C11 C10 C9 128.5(4) . . ?
C12 C11 C10 107.0(4) . . ?
C12 C11 H11 126.5 . . ?
C10 C11 H11 126.5 . . ?
C11 C12 C13 107.5(4) . . ?
C11 C12 H12 126.2 . . ?
C13 C12 H12 126.2 . . ?
N3 C13 C14 123.9(4) . . ?
N3 C13 C12 108.9(4) . . ?
C14 C13 C12 127.2(4) . . ?
C15 C14 C13 126.6(4) . . ?
C15 C14 C32 117.0(4) . . ?
C13 C14 C32 116.4(4) . . ?
C14 C15 N4 124.3(4) . . ?
C14 C15 C16 128.5(4) . . ?
N4 C15 C16 107.2(4) . . ?
C17 C16 C15 107.7(4) . . ?
C17 C16 H16 126.2 . . ?
C15 C16 H16 126.2 . . ?
C16 C17 C18 106.4(4) . . ?
C16 C17 H17 126.8 . . ?
C18 C17 H17 126.8 . . ?
N4 C18 C17 112.2(4) . . ?
N4 C18 H18 123.9 . . ?
C17 C18 H18 123.9 . . ?
C24 C19 C20 119.0(4) . . ?
C24 C19 C5 120.5(4) . . ?
C20 C19 C5 120.5(4) . . ?
C21 C20 C19 120.2(5) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C20 C21 C22 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.6(4) . . ?
C21 C22 C25 117.8(4) . . ?
C23 C22 C25 122.4(5) . . ?
C22 C23 C24 119.3(4) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C19 C24 C23 121.0(4) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
O1 C25 N5 121.8(4) . . ?
O1 C25 C22 120.7(4) . . ?
N5 C25 C22 117.5(4) . . ?
C27 C26 C31 118.9(5) . . ?
C27 C26 N5 120.5(5) . . ?
C31 C26 N5 120.6(5) . . ?
C26 C27 C28 121.5(6) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C29 C28 C27 120.3(7) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 121.0(6) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C29 C30 C31 118.7(7) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C26 C31 C30 119.7(6) . . ?
C26 C31 H31 120.1 . . ?
C30 C31 H31 120.1 . . ?
C37 C32 C33 118.9(4) . . ?
C37 C32 C14 121.8(5) . . ?
C33 C32 C14 119.2(5) . . ?
C34 C33 C32 119.2(6) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C35 C34 C33 121.0(6) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C36 C35 C34 119.1(5) . . ?
C36 C35 C38 121.0(7) . . ?
C34 C35 C38 119.8(7) . . ?
C35 C36 C37 121.2(6) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C32 C37 C36 120.5(5) . . ?
C32 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N6 C39 C40 112.6(4) . . ?
N6 C39 H39 123.7 . . ?
C40 C39 H39 123.7 . . ?
C41 C40 C39 105.8(4) . . ?
C41 C40 H40 127.1 . . ?
C39 C40 H40 127.1 . . ?
C40 C41 C42 107.5(4) . . ?
C40 C41 H41 126.2 . . ?
C42 C41 H41 126.2 . . ?
C43 C42 N6 124.1(4) . . ?
C43 C42 C41 127.6(4) . . ?
N6 C42 C41 108.3(4) . . ?
C42 C43 C44 126.5(4) . . ?
C42 C43 C70 116.0(4) . . ?
C44 C43 C70 117.5(4) . . ?
N7 C44 C43 124.7(4) . . ?
N7 C44 C45 107.9(4) . . ?
C43 C44 C45 127.3(4) . . ?
C46 C45 C44 107.9(4) . . ?
C46 C45 H45 126.0 . . ?
C44 C45 H45 126.0 . . ?
C45 C46 C47 106.7(4) . . ?
C45 C46 H46 126.7 . . ?
C47 C46 H46 126.7 . . ?
N7 C47 C46 110.6(4) . . ?
N7 C47 C48 119.5(4) . . ?
C46 C47 C48 129.8(4) . . ?
N8 C48 C49 109.9(4) . . ?
N8 C48 C47 120.2(4) . . ?
C49 C48 C47 129.6(4) . . ?
C50 C49 C48 107.2(4) . . ?
C50 C49 H49 126.4 . . ?
C48 C49 H49 126.4 . . ?
C49 C50 C51 107.7(4) . . ?
C49 C50 H50 126.1 . . ?
C51 C50 H50 126.1 . . ?
N8 C51 C52 125.2(4) . . ?
N8 C51 C50 107.6(4) . . ?
C52 C51 C50 127.0(4) . . ?
C53 C52 C51 126.3(4) . . ?
C53 C52 C57 116.6(4) . . ?
C51 C52 C57 117.1(4) . . ?
N9 C53 C52 124.6(4) . . ?
N9 C53 C54 107.5(4) . . ?
C52 C53 C54 127.9(4) . . ?
C55 C54 C53 107.4(4) . . ?
C55 C54 H54 126.3 . . ?
C53 C54 H54 126.3 . . ?
C54 C55 C56 106.2(4) . . ?
C54 C55 H55 126.9 . . ?
C56 C55 H55 126.9 . . ?
N9 C56 C55 112.2(4) . . ?
N9 C56 H56 123.9 . . ?
C55 C56 H56 123.9 . . ?
C62 C57 C58 118.4(4) . . ?
C62 C57 C52 121.8(4) . . ?
C58 C57 C52 119.8(4) . . ?
C57 C58 C59 120.6(4) . . ?
C57 C58 H58 119.7 . . ?
C59 C58 H58 119.7 . . ?
C58 C59 C60 119.9(4) . . ?
C58 C59 H59 120.1 . . ?
C60 C59 H59 120.1 . . ?
C61 C60 C59 119.4(4) . . ?
C61 C60 C63 123.1(4) . . ?
C59 C60 C63 117.4(4) . . ?
C62 C61 C60 120.0(4) . . ?
C62 C61 H61 120.0 . . ?
C60 C61 H61 120.0 . . ?
C61 C62 C57 121.7(4) . . ?
C61 C62 H62 119.2 . . ?
C57 C62 H62 119.2 . . ?
O2 C63 N10 124.0(4) . . ?
O2 C63 C60 122.6(4) . . ?
N10 C63 C60 113.4(4) . . ?
C69 C64 C65 119.3(5) . . ?
C69 C64 H64 120.4 . . ?
C65 C64 H64 120.4 . . ?
C66 C65 C64 121.1(5) . . ?
C66 C65 H65 119.4 . . ?
C64 C65 H65 119.4 . . ?
C65 C66 C67 119.3(5) . . ?
C65 C66 H66 120.4 . . ?
C67 C66 H66 120.4 . . ?
C68 C67 C66 120.8(6) . . ?
C68 C67 H67 119.6 . . ?
C66 C67 H67 119.6 . . ?
C67 C68 C69 119.3(5) . . ?
C67 C68 H68 120.3 . . ?
C69 C68 H68 120.3 . . ?
C64 C69 C68 120.1(4) . . ?
C64 C69 N10 123.0(4) . . ?
C68 C69 N10 116.8(4) . . ?
C71 C70 C75 116.9(4) . . ?
C71 C70 C43 121.2(4) . . ?
C75 C70 C43 121.8(4) . . ?
C70 C71 C72 121.4(5) . . ?
C70 C71 H71 119.3 . . ?
C72 C71 H71 119.3 . . ?
C73 C72 C71 121.7(6) . . ?
C73 C72 H72 119.1 . . ?
C71 C72 H72 119.1 . . ?
C72 C73 C74 117.8(5) . . ?
C72 C73 C76 121.9(6) . . ?
C74 C73 C76 120.2(6) . . ?
C73 C74 C75 119.7(6) . . ?
C73 C74 H74 120.1 . . ?
C75 C74 H74 120.1 . . ?
C70 C75 C74 122.2(6) . . ?
C70 C75 H75 118.9 . . ?
C74 C75 H75 118.9 . . ?
C73 C76 H76A 109.5 . . ?
C73 C76 H76B 109.5 . . ?
H76A C76 H76B 109.5 . . ?
C73 C76 H76C 109.5 . . ?
H76A C76 H76C 109.5 . . ?
H76B C76 H76C 109.5 . . ?
C1 N1 C4 105.7(3) . . ?
C1 N1 Zn1 128.7(3) . . ?
C4 N1 Zn1 125.3(3) . . ?
C9 N2 C6 106.7(3) . . ?
C9 N2 Zn1 124.6(3) . . ?
C6 N2 Zn1 121.6(3) . . ?
C10 N3 C13 105.6(3) . . ?
C10 N3 Zn2 125.3(3) . . ?
C13 N3 Zn2 123.1(3) . . ?
C18 N4 C15 106.6(3) . . ?
C18 N4 Zn2 127.9(3) . . ?
C15 N4 Zn2 124.9(3) . . ?
C25 N5 C26 121.9(4) . . ?
C25 N5 H5 119.1 . . ?
C26 N5 H5 119.1 . . ?
C39 N6 C42 105.7(4) . . ?
C39 N6 Zn1 127.8(3) . . ?
C42 N6 Zn1 126.1(3) . . ?
C47 N7 C44 106.9(3) . . ?
C47 N7 Zn1 125.9(3) . . ?
C44 N7 Zn1 124.4(3) . . ?
C48 N8 C51 107.5(3) . . ?
C48 N8 Zn2 124.3(3) . . ?
C51 N8 Zn2 121.9(3) . . ?
C56 N9 C53 106.7(4) . . ?
C56 N9 Zn2 128.0(3) . . ?
C53 N9 Zn2 125.0(3) . . ?
C63 N10 C69 126.2(4) . . ?
C63 N10 H10 116.9 . . ?
C69 N10 H10 116.9 . . ?
N6 Zn1 N1 126.37(18) . . ?
N6 Zn1 N7 92.51(14) . . ?
N1 Zn1 N7 109.08(14) . . ?
N6 Zn1 N2 100.35(15) . . ?
N1 Zn1 N2 92.89(13) . . ?
N7 Zn1 N2 140.56(15) . . ?
N4 Zn2 N3 93.31(13) . . ?
N4 Zn2 N9 127.84(16) . . ?
N3 Zn2 N9 107.01(14) . . ?
N4 Zn2 N8 102.71(14) . . ?
N3 Zn2 N8 137.91(16) . . ?
N9 Zn2 N8 93.40(13) . . ?

_refine_diff_density_max         1.336
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.072






#===END




####################################################################### 
# 
# 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_compound10
_database_code_depnum_ccdc_archive 'CCDC 1817914'
_audit_update_record             
;
2018-01-18 deposited with the CCDC.
2018-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H26 N4 O2'
_chemical_formula_weight         510.58

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      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                   7.4764(5)
_cell_length_b                   9.8577(7)
_cell_length_c                   18.0856(12)
_cell_angle_alpha                94.177(3)
_cell_angle_beta                 90.378(3)
_cell_angle_gamma                98.712(3)
_cell_volume                     1313.82(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9456
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.57

_exptl_crystal_description       rod
_exptl_crystal_colour            dark-purple
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_T_max  0.996
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34392
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         30.111
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             7024
_reflns_number_gt                4830
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.1771P)²+1.7932P] 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         7024
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.1045
_refine_ls_wR_factor_ref         0.3286
_refine_ls_wR_factor_gt          0.3061
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.6769(6) 0.5645(4) 0.5888(2) 0.0481(9) Uani 1 1 d . . . . .
H1 H 0.572497 0.496274 0.588821 0.058 Uiso 1 1 calc R U . . .
C2 C 0.8111(6) 0.5689(4) 0.5378(2) 0.0464(9) Uani 1 1 d . . . . .
H2 H 0.817089 0.504512 0.496499 0.056 Uiso 1 1 calc R U . . .
C3 C 0.9380(5) 0.6855(4) 0.55739(19) 0.0398(8) Uani 1 1 d . . . . .
H3 H 1.045610 0.714930 0.531653 0.048 Uiso 1 1 calc R U . . .
C4 C 0.8784(5) 0.7506(3) 0.62140(19) 0.0345(7) Uani 1 1 d . . . . .
C5 C 0.9554(4) 0.8744(3) 0.66350(17) 0.0317(7) Uani 1 1 d . . . . .
C6 C 0.8756(4) 0.9274(3) 0.72558(18) 0.0317(7) Uani 1 1 d . . . . .
C7 C 0.9390(5) 1.0507(4) 0.7721(2) 0.0385(8) Uani 1 1 d . . . . .
H7 H 1.049714 1.110836 0.767625 0.046 Uiso 1 1 calc R U . . .
C8 C 0.8107(5) 1.0645(4) 0.8234(2) 0.0387(8) Uani 1 1 d . . . . .
H8 H 0.812674 1.136387 0.861466 0.046 Uiso 1 1 calc R U . . .
C9 C 0.6705(4) 0.9480(3) 0.80846(17) 0.0316(7) Uani 1 1 d . . . . .
C10 C 1.1269(4) 0.9506(3) 0.63670(17) 0.0308(7) Uani 1 1 d . . . . .
C11 C 1.1299(5) 1.0702(4) 0.6011(3) 0.0565(12) Uani 1 1 d . . . . .
H11 H 1.019821 1.104749 0.593571 0.068 Uiso 1 1 calc R U . . .
C12 C 1.2891(6) 1.1407(4) 0.5763(3) 0.0530(11) Uani 1 1 d . . . . .
H12 H 1.285665 1.221905 0.551408 0.064 Uiso 1 1 calc R U . . .
C13 C 1.4514(5) 1.0969(4) 0.58664(18) 0.0359(7) Uani 1 1 d . . . . .
C14 C 1.4506(5) 0.9764(5) 0.6217(2) 0.0492(10) Uani 1 1 d . . . . .
H14 H 1.561369 0.942801 0.629278 0.059 Uiso 1 1 calc R U . . .
C15 C 1.2916(5) 0.9045(4) 0.6458(2) 0.0473(9) Uani 1 1 d . . . . .
H15 H 1.294837 0.821670 0.669234 0.057 Uiso 1 1 calc R U . . .
C16 C 1.6251(5) 1.1772(4) 0.5610(2) 0.0506(10) Uani 1 1 d . . . . .
H16A H 1.599259 1.228025 0.518578 0.076 Uiso 1 1 calc R U . . .
H16B H 1.709483 1.113516 0.546186 0.076 Uiso 1 1 calc R U . . .
H16C H 1.679451 1.242034 0.601510 0.076 Uiso 1 1 calc R U . . .
C17 C 0.5045(4) 0.9168(3) 0.84753(17) 0.0308(7) Uani 1 1 d . . . . .
C18 C 0.4368(5) 0.9864(3) 0.90852(18) 0.0344(7) Uani 1 1 d . . . . .
H18 H 0.493834 1.069661 0.933899 0.041 Uiso 1 1 calc R U . . .
C19 C 0.2707(5) 0.9122(3) 0.92546(18) 0.0337(7) Uani 1 1 d . . . . .
H19 H 0.194182 0.934905 0.964696 0.040 Uiso 1 1 calc R U . . .
C20 C 0.2370(4) 0.7969(3) 0.87369(17) 0.0286(6) Uani 1 1 d . . . . .
C21 C 0.0859(4) 0.6895(3) 0.86527(16) 0.0265(6) Uani 1 1 d . . . . .
C22 C 0.0614(4) 0.5935(3) 0.80521(16) 0.0287(6) Uani 1 1 d . . . . .
C23 C -0.0790(5) 0.4768(3) 0.79304(18) 0.0331(7) Uani 1 1 d . . . . .
H23 H -0.176207 0.450107 0.825050 0.040 Uiso 1 1 calc R U . . .
C24 C -0.0454(5) 0.4122(4) 0.7269(2) 0.0420(8) Uani 1 1 d . . . . .
H24 H -0.113544 0.331133 0.703533 0.050 Uiso 1 1 calc R U . . .
C25 C 0.1146(5) 0.4916(4) 0.69953(19) 0.0410(8) Uani 1 1 d . . . . .
H25 H 0.167043 0.469584 0.653341 0.049 Uiso 1 1 calc R U . . .
C26 C -0.0472(4) 0.6822(3) 0.92587(16) 0.0258(6) Uani 1 1 d . . . . .
C27 C -0.2313(4) 0.6825(3) 0.91222(16) 0.0289(6) Uani 1 1 d . . . . .
H27 H -0.273757 0.685538 0.862825 0.035 Uiso 1 1 calc R U . . .
C28 C -0.3524(4) 0.6783(3) 0.96963(17) 0.0310(6) Uani 1 1 d . . . . .
H28 H -0.477204 0.678423 0.959534 0.037 Uiso 1 1 calc R U . . .
C29 C -0.2918(4) 0.6739(3) 1.04250(16) 0.0272(6) Uani 1 1 d . . . . .
C30 C -0.1087(4) 0.6722(3) 1.05618(17) 0.0280(6) Uani 1 1 d . . . . .
H30 H -0.066603 0.668270 1.105528 0.034 Uiso 1 1 calc R U . . .
C31 C 0.0119(4) 0.6762(3) 0.99885(17) 0.0289(6) Uani 1 1 d . . . . .
H31 H 0.136431 0.674932 1.009034 0.035 Uiso 1 1 calc R U . . .
C32 C -0.4227(4) 0.6743(3) 1.10303(17) 0.0292(6) Uani 1 1 d . . . . .
C33 C -0.4559(6) 0.6947(6) 1.2334(2) 0.0623(13) Uani 1 1 d . . . . .
H33A H -0.541620 0.758379 1.225243 0.093 Uiso 1 1 calc R U . . .
H33B H -0.381516 0.727739 1.277719 0.093 Uiso 1 1 calc R U . . .
H33C H -0.522742 0.603105 1.240190 0.093 Uiso 1 1 calc R U . . .
N1 N 0.7169(4) 0.6728(3) 0.63930(18) 0.0421(7) Uani 1 1 d . . . . .
H1A H 0.650417 0.691114 0.677665 0.050 Uiso 1 1 calc R U . . .
N2 N 0.7088(4) 0.8660(3) 0.75128(14) 0.0297(6) Uani 1 1 d . . . . .
N3 N 0.3826(4) 0.8038(3) 0.82771(14) 0.0293(6) Uani 1 1 d . . . . .
H3A H 0.395045 0.743248 0.790595 0.035 Uiso 1 1 calc R U . . .
N4 N 0.1803(4) 0.5973(3) 0.74488(15) 0.0345(6) Uani 1 1 d . . . . .
O1 O -0.5850(3) 0.6668(3) 1.09497(13) 0.0371(6) Uani 1 1 d . . . . .
O2 O -0.3409(3) 0.6871(3) 1.16995(13) 0.0465(7) 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 1.349(5) . ?
C1 C2 1.366(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(5) . ?
C3 H3 0.9500 . ?
C4 N1 1.383(4) . ?
C4 C5 1.431(5) . ?
C5 C6 1.381(4) . ?
C5 C10 1.487(4) . ?
C6 N2 1.399(4) . ?
C6 C7 1.443(5) . ?
C7 C8 1.353(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.442(5) . ?
C8 H8 0.9500 . ?
C9 N2 1.325(4) . ?
C9 C17 1.436(4) . ?
C10 C11 1.381(5) . ?
C10 C15 1.388(5) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.364(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(5) . ?
C13 C16 1.510(5) . ?
C14 C15 1.380(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N3 1.353(4) . ?
C17 C18 1.395(4) . ?
C18 C19 1.390(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.409(4) . ?
C19 H19 0.9500 . ?
C20 N3 1.371(4) . ?
C20 C21 1.426(4) . ?
C21 C22 1.380(4) . ?
C21 C26 1.483(4) . ?
C22 N4 1.411(4) . ?
C22 C23 1.438(5) . ?
C23 C24 1.356(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.438(5) . ?
C24 H24 0.9500 . ?
C25 N4 1.310(5) . ?
C25 H25 0.9500 . ?
C26 C31 1.397(4) . ?
C26 C27 1.398(4) . ?
C27 C28 1.381(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.397(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.392(4) . ?
C29 C32 1.474(4) . ?
C30 C31 1.377(4) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 O1 1.211(4) . ?
C32 O2 1.341(4) . ?
C33 O2 1.442(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
N1 H1A 0.8800 . ?
N3 H3A 0.8800 . ?

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 108.9(4) . . ?
N1 C1 H1 125.6 . . ?
C2 C1 H1 125.6 . . ?
C1 C2 C3 107.5(3) . . ?
C1 C2 H2 126.3 . . ?
C3 C2 H2 126.3 . . ?
C4 C3 C2 107.7(3) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
N1 C4 C3 106.5(3) . . ?
N1 C4 C5 123.0(3) . . ?
C3 C4 C5 130.6(3) . . ?
C6 C5 C4 123.3(3) . . ?
C6 C5 C10 119.3(3) . . ?
C4 C5 C10 117.4(3) . . ?
C5 C6 N2 122.4(3) . . ?
C5 C6 C7 128.4(3) . . ?
N2 C6 C7 109.1(3) . . ?
C8 C7 C6 107.0(3) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
C7 C8 C9 106.0(3) . . ?
C7 C8 H8 127.0 . . ?
C9 C8 H8 127.0 . . ?
N2 C9 C17 120.5(3) . . ?
N2 C9 C8 112.1(3) . . ?
C17 C9 C8 127.3(3) . . ?
C11 C10 C15 116.7(3) . . ?
C11 C10 C5 121.6(3) . . ?
C15 C10 C5 121.7(3) . . ?
C12 C11 C10 121.6(3) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 121.7(3) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 117.5(3) . . ?
C12 C13 C16 121.1(4) . . ?
C14 C13 C16 121.4(4) . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 121.4(3) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 C18 107.8(3) . . ?
N3 C17 C9 121.7(3) . . ?
C18 C17 C9 130.6(3) . . ?
C19 C18 C17 107.7(3) . . ?
C19 C18 H18 126.1 . . ?
C17 C18 H18 126.1 . . ?
C18 C19 C20 107.4(3) . . ?
C18 C19 H19 126.3 . . ?
C20 C19 H19 126.3 . . ?
N3 C20 C19 106.8(3) . . ?
N3 C20 C21 122.7(3) . . ?
C19 C20 C21 130.5(3) . . ?
C22 C21 C20 123.3(3) . . ?
C22 C21 C26 119.9(3) . . ?
C20 C21 C26 116.8(3) . . ?
C21 C22 N4 122.6(3) . . ?
C21 C22 C23 128.1(3) . . ?
N4 C22 C23 109.3(3) . . ?
C24 C23 C22 106.6(3) . . ?
C24 C23 H23 126.7 . . ?
C22 C23 H23 126.7 . . ?
C23 C24 C25 106.0(3) . . ?
C23 C24 H24 127.0 . . ?
C25 C24 H24 127.0 . . ?
N4 C25 C24 113.0(3) . . ?
N4 C25 H25 123.5 . . ?
C24 C25 H25 123.5 . . ?
C31 C26 C27 118.6(3) . . ?
C31 C26 C21 119.6(3) . . ?
C27 C26 C21 121.8(3) . . ?
C28 C27 C26 120.8(3) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 120.2(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C30 C29 C28 119.1(3) . . ?
C30 C29 C32 121.7(3) . . ?
C28 C29 C32 119.1(3) . . ?
C31 C30 C29 120.6(3) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C26 120.6(3) . . ?
C30 C31 H31 119.7 . . ?
C26 C31 H31 119.7 . . ?
O1 C32 O2 122.8(3) . . ?
O1 C32 C29 125.3(3) . . ?
O2 C32 C29 111.9(3) . . ?
O2 C33 H33A 109.5 . . ?
O2 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O2 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C1 N1 C4 109.5(3) . . ?
C1 N1 H1A 125.3 . . ?
C4 N1 H1A 125.3 . . ?
C9 N2 C6 105.7(3) . . ?
C17 N3 C20 110.3(3) . . ?
C17 N3 H3A 124.8 . . ?
C20 N3 H3A 124.8 . . ?
C25 N4 C22 105.1(3) . . ?
C32 O2 C33 116.6(3) . . ?

_refine_diff_density_max         0.786
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.112

