# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_wl593
_database_code_depnum_ccdc_archive 'CCDC 2209653'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2023-03-24 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 H45 N3'
_chemical_formula_weight         555.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.797(3)
_cell_length_b                   10.878(3)
_cell_length_c                   30.575(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.548(17)
_cell_angle_gamma                90
_cell_volume                     3237.3(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    41100
_cell_measurement_theta_min      2.732
_cell_measurement_theta_max      27.656

_exptl_crystal_description       block
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.6481
_exptl_absorpt_correction_T_max  0.7319
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41100
_diffrn_reflns_av_unetI/netI     0.1291
_diffrn_reflns_av_R_equivalents  0.1076
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.732
_diffrn_reflns_theta_max         27.656
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7448
_reflns_number_gt                4328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+0.4909P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0085(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7448
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1 N 0.43657(17) 0.71038(14) 0.37441(5) 0.0247(4) Uani 1 1 d . . . . .
N2 N 0.41181(17) 0.70328(14) 0.33098(5) 0.0265(4) Uani 1 1 d . . . . .
N3 N 0.50261(17) 0.61662(14) 0.32100(5) 0.0245(4) Uani 1 1 d . . . . .
C4 C 0.5844(2) 0.56749(17) 0.35738(6) 0.0250(5) Uani 1 1 d . . . . .
C5 C 0.5375(2) 0.63498(17) 0.39299(6) 0.0245(5) Uani 1 1 d . . . . .
C6 C 0.3594(2) 0.80273(18) 0.39579(6) 0.0268(5) Uani 1 1 d . . . . .
C7 C 0.2255(2) 0.77451(19) 0.40417(6) 0.0305(5) Uani 1 1 d . . . . .
C8 C 0.1583(2) 0.8628(2) 0.42673(7) 0.0384(6) Uani 1 1 d . . . . .
H8 H 0.067180 0.847842 0.433181 0.046 Uiso 1 1 calc R U . . .
C9 C 0.2218(3) 0.9713(2) 0.43978(7) 0.0453(6) Uani 1 1 d . . . . .
H9 H 0.174973 1.029715 0.455710 0.054 Uiso 1 1 calc R U . . .
C10 C 0.3524(3) 0.9964(2) 0.43009(7) 0.0411(6) Uani 1 1 d . . . . .
H10 H 0.393761 1.072721 0.439072 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4256(2) 0.91292(18) 0.40745(6) 0.0318(5) Uani 1 1 d . . . . .
C12 C 0.1534(2) 0.6558(2) 0.38988(7) 0.0358(5) Uani 1 1 d . . . . .
H12 H 0.216314 0.605894 0.373370 0.043 Uiso 1 1 calc R U . . .
C13 C 0.0218(3) 0.6818(3) 0.35918(8) 0.0698(9) Uani 1 1 d . . . . .
H13A H 0.044668 0.727131 0.333292 0.105 Uiso 1 1 calc R U . . .
H13B H -0.041016 0.730998 0.374812 0.105 Uiso 1 1 calc R U . . .
H13C H -0.022525 0.603892 0.349798 0.105 Uiso 1 1 calc R U . . .
C14 C 0.1187(3) 0.5812(2) 0.42906(7) 0.0465(6) Uani 1 1 d . . . . .
H14A H 0.056068 0.628430 0.445430 0.070 Uiso 1 1 calc R U . . .
H14B H 0.203123 0.563000 0.448342 0.070 Uiso 1 1 calc R U . . .
H14C H 0.074393 0.504155 0.418702 0.070 Uiso 1 1 calc R U . . .
C15 C 0.5684(2) 0.94416(19) 0.39682(7) 0.0373(6) Uani 1 1 d . . . . .
H15 H 0.604232 0.872070 0.381340 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5638(3) 1.0546(2) 0.36573(8) 0.0561(7) Uani 1 1 d . . . . .
H16A H 0.656506 1.071661 0.358134 0.084 Uiso 1 1 calc R U . . .
H16B H 0.529331 1.126677 0.380269 0.084 Uiso 1 1 calc R U . . .
H16C H 0.502771 1.036361 0.338856 0.084 Uiso 1 1 calc R U . . .
C17 C 0.6669(3) 0.9688(2) 0.43850(8) 0.0536(7) Uani 1 1 d . . . . .
H17A H 0.759903 0.981808 0.430510 0.080 Uiso 1 1 calc R U . . .
H17B H 0.666936 0.898027 0.458341 0.080 Uiso 1 1 calc R U . . .
H17C H 0.636940 1.042251 0.453308 0.080 Uiso 1 1 calc R U . . .
C18 C 0.4955(2) 0.57741(17) 0.27583(6) 0.0243(5) Uani 1 1 d . . . . .
C19 C 0.3910(2) 0.49558(19) 0.26063(6) 0.0305(5) Uani 1 1 d . . . . .
C20 C 0.3797(2) 0.4651(2) 0.21608(7) 0.0363(5) Uani 1 1 d . . . . .
H20 H 0.308974 0.410816 0.204239 0.044 Uiso 1 1 calc R U . . .
C21 C 0.4694(2) 0.5124(2) 0.18914(7) 0.0357(5) Uani 1 1 d . . . . .
H21 H 0.458339 0.492186 0.158716 0.043 Uiso 1 1 calc R U . . .
C22 C 0.5761(2) 0.58922(18) 0.20560(6) 0.0310(5) Uani 1 1 d . . . . .
H22 H 0.638834 0.618697 0.186544 0.037 Uiso 1 1 calc R U . . .
C23 C 0.5921(2) 0.62355(17) 0.24967(6) 0.0258(5) Uani 1 1 d . . . . .
C24 C 0.2937(2) 0.4413(2) 0.29091(7) 0.0398(6) Uani 1 1 d . . . . .
H24 H 0.289035 0.500837 0.315608 0.048 Uiso 1 1 calc R U . A 1
C25 C 0.1536(9) 0.4183(9) 0.2718(3) 0.0548(11) Uani 0.322(3) 1 d . . P B 1
H25A H 0.119035 0.489793 0.254437 0.082 Uiso 0.322(3) 1 calc R U P B 1
H25B H 0.095542 0.403688 0.295354 0.082 Uiso 0.322(3) 1 calc R U P B 1
H25C H 0.151456 0.345801 0.252692 0.082 Uiso 0.322(3) 1 calc R U P B 1
C26 C 0.3598(11) 0.3171(8) 0.3120(3) 0.0607(12) Uani 0.322(3) 1 d . . P B 1
H26A H 0.366066 0.256172 0.288686 0.091 Uiso 0.322(3) 1 calc R U P B 1
H26B H 0.301883 0.284752 0.333443 0.091 Uiso 0.322(3) 1 calc R U P B 1
H26C H 0.451918 0.334261 0.326762 0.091 Uiso 0.322(3) 1 calc R U P B 1
C25A C 0.1496(4) 0.5070(5) 0.27949(13) 0.0548(11) Uani 0.678(3) 1 d . . P B 2
H25D H 0.112996 0.487908 0.249075 0.082 Uiso 0.678(3) 1 calc R U P B 2
H25E H 0.161175 0.596120 0.282806 0.082 Uiso 0.678(3) 1 calc R U P B 2
H25F H 0.085456 0.477593 0.299540 0.082 Uiso 0.678(3) 1 calc R U P B 2
C26A C 0.2790(5) 0.3047(4) 0.28574(15) 0.0607(12) Uani 0.678(3) 1 d . . P B 2
H26D H 0.245502 0.285148 0.255097 0.091 Uiso 0.678(3) 1 calc R U P B 2
H26E H 0.213362 0.274219 0.305107 0.091 Uiso 0.678(3) 1 calc R U P B 2
H26F H 0.368408 0.265439 0.293640 0.091 Uiso 0.678(3) 1 calc R U P B 2
C27 C 0.7076(2) 0.70701(18) 0.26887(6) 0.0283(5) Uani 1 1 d . . . . .
H27 H 0.737375 0.677502 0.299449 0.034 Uiso 1 1 calc R U . . .
C28 C 0.6585(3) 0.83915(19) 0.27252(8) 0.0413(6) Uani 1 1 d . . . . .
H28A H 0.632277 0.872475 0.242980 0.062 Uiso 1 1 calc R U . . .
H28B H 0.732768 0.889002 0.287659 0.062 Uiso 1 1 calc R U . . .
H28C H 0.579035 0.840962 0.289270 0.062 Uiso 1 1 calc R U . . .
C29 C 0.8341(2) 0.7039(2) 0.24375(7) 0.0382(6) Uani 1 1 d . . . . .
H29A H 0.866182 0.618916 0.241913 0.057 Uiso 1 1 calc R U . . .
H29B H 0.907161 0.754238 0.259269 0.057 Uiso 1 1 calc R U . . .
H29C H 0.809840 0.736481 0.214002 0.057 Uiso 1 1 calc R U . . .
C30 C 0.6815(2) 0.47879(18) 0.35200(6) 0.0278(5) Uani 1 1 d . . . . .
H30 H 0.703531 0.470016 0.322699 0.033 Uiso 1 1 calc R U . . .
C31 C 0.7549(2) 0.39737(17) 0.38336(6) 0.0263(5) Uani 1 1 d . . . . .
C32 C 0.8696(2) 0.33252(18) 0.37131(7) 0.0307(5) Uani 1 1 d . . . . .
H32 H 0.898799 0.346966 0.343174 0.037 Uiso 1 1 calc R U . . .
C33 C 0.9408(2) 0.24875(19) 0.39913(7) 0.0359(5) Uani 1 1 d . . . . .
H33 H 1.017055 0.206204 0.389790 0.043 Uiso 1 1 calc R U . . .
C34 C 0.9022(2) 0.22631(19) 0.44031(7) 0.0361(6) Uani 1 1 d . . . . .
H34 H 0.952006 0.169350 0.459558 0.043 Uiso 1 1 calc R U . . .
C35 C 0.7901(2) 0.28783(19) 0.45323(7) 0.0352(5) Uani 1 1 d . . . . .
H35 H 0.762393 0.272515 0.481509 0.042 Uiso 1 1 calc R U . . .
C36 C 0.7177(2) 0.37163(18) 0.42539(6) 0.0313(5) Uani 1 1 d . . . . .
H36 H 0.640868 0.412685 0.435006 0.038 Uiso 1 1 calc R U . . .
C37 C 0.5981(2) 0.64831(17) 0.43876(6) 0.0256(5) Uani 1 1 d . . . . .
C38 C 0.5203(2) 0.66922(18) 0.47359(6) 0.0297(5) Uani 1 1 d . . . . .
H38 H 0.422820 0.669133 0.468260 0.036 Uiso 1 1 calc R U . . .
C39 C 0.5833(2) 0.69000(18) 0.51565(6) 0.0319(5) Uani 1 1 d . . . . .
H39 H 0.529007 0.706008 0.538853 0.038 Uiso 1 1 calc R U . . .
C40 C 0.7247(2) 0.68767(19) 0.52423(7) 0.0348(5) Uani 1 1 d . . . . .
H40 H 0.767641 0.703288 0.553144 0.042 Uiso 1 1 calc R U . . .
C41 C 0.8038(2) 0.66243(19) 0.49045(7) 0.0349(5) Uani 1 1 d . . . . .
H41 H 0.901031 0.658369 0.496372 0.042 Uiso 1 1 calc R U . . .
C42 C 0.7410(2) 0.64318(18) 0.44816(6) 0.0301(5) Uani 1 1 d . . . . .
H42 H 0.795784 0.626214 0.425165 0.036 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
N1 N2 1.324(2) . ?
N1 C5 1.359(2) . ?
N1 C6 1.456(2) . ?
N2 N3 1.355(2) . ?
N3 C4 1.400(2) . ?
N3 C18 1.439(2) . ?
C4 C30 1.378(3) . ?
C4 C5 1.432(3) . ?
C5 C37 1.464(3) . ?
C6 C11 1.390(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.392(3) . ?
C7 C12 1.512(3) . ?
C8 C9 1.372(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C15 1.511(3) . ?
C12 C14 1.517(3) . ?
C12 C13 1.533(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.530(3) . ?
C15 C17 1.532(3) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.395(3) . ?
C18 C23 1.400(3) . ?
C19 C20 1.394(3) . ?
C19 C24 1.522(3) . ?
C20 C21 1.371(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 C27 1.516(3) . ?
C24 C25 1.451(9) . ?
C24 C26A 1.499(4) . ?
C24 C25A 1.585(5) . ?
C24 C26 1.602(10) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 0.9800 . ?
C26A H26D 0.9800 . ?
C26A H26E 0.9800 . ?
C26A H26F 0.9800 . ?
C27 C28 1.524(3) . ?
C27 C29 1.531(3) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.437(3) . ?
C30 H30 0.9500 . ?
C31 C36 1.404(3) . ?
C31 C32 1.411(3) . ?
C32 C33 1.380(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.377(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.398(3) . ?
C37 C42 1.398(3) . ?
C38 C39 1.380(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.380(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.388(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.383(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 115.18(15) . . ?
N2 N1 C6 116.43(15) . . ?
C5 N1 C6 128.25(16) . . ?
N1 N2 N3 102.50(15) . . ?
N2 N3 C4 114.69(15) . . ?
N2 N3 C18 117.45(15) . . ?
C4 N3 C18 127.56(16) . . ?
C30 C4 N3 120.85(17) . . ?
C30 C4 C5 137.34(19) . . ?
N3 C4 C5 101.79(17) . . ?
N1 C5 C4 105.83(16) . . ?
N1 C5 C37 122.45(17) . . ?
C4 C5 C37 130.38(19) . . ?
C11 C6 C7 124.18(19) . . ?
C11 C6 N1 117.36(18) . . ?
C7 C6 N1 118.45(17) . . ?
C8 C7 C6 116.5(2) . . ?
C8 C7 C12 120.1(2) . . ?
C6 C7 C12 123.44(18) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C6 116.1(2) . . ?
C10 C11 C15 120.2(2) . . ?
C6 C11 C15 123.72(19) . . ?
C7 C12 C14 111.57(18) . . ?
C7 C12 C13 110.62(19) . . ?
C14 C12 C13 109.47(19) . . ?
C7 C12 H12 108.4 . . ?
C14 C12 H12 108.4 . . ?
C13 C12 H12 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 110.4(2) . . ?
C11 C15 C17 111.80(19) . . ?
C16 C15 C17 110.53(19) . . ?
C11 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C17 C15 H15 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 123.79(17) . . ?
C19 C18 N3 117.53(17) . . ?
C23 C18 N3 118.68(17) . . ?
C20 C19 C18 116.82(19) . . ?
C20 C19 C24 121.08(19) . . ?
C18 C19 C24 122.11(18) . . ?
C21 C20 C19 120.8(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 121.07(19) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C23 120.72(19) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 116.66(19) . . ?
C22 C23 C27 122.22(18) . . ?
C18 C23 C27 121.12(17) . . ?
C25 C24 C19 116.9(4) . . ?
C26A C24 C19 112.3(2) . . ?
C26A C24 C25A 110.6(3) . . ?
C19 C24 C25A 107.2(2) . . ?
C25 C24 C26 109.7(5) . . ?
C19 C24 C26 108.6(4) . . ?
C25 C24 H24 107.1 . . ?
C19 C24 H24 107.1 . . ?
C26 C24 H24 107.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C25A H25D 109.5 . . ?
C24 C25A H25E 109.5 . . ?
H25D C25A H25E 109.5 . . ?
C24 C25A H25F 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
C24 C26A H26D 109.5 . . ?
C24 C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C24 C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C23 C27 C28 111.44(18) . . ?
C23 C27 C29 113.81(16) . . ?
C28 C27 C29 109.74(17) . . ?
C23 C27 H27 107.2 . . ?
C28 C27 H27 107.2 . . ?
C29 C27 H27 107.2 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C4 C30 C31 130.70(18) . . ?
C4 C30 H30 114.6 . . ?
C31 C30 H30 114.6 . . ?
C36 C31 C32 115.93(19) . . ?
C36 C31 C30 124.84(19) . . ?
C32 C31 C30 119.16(18) . . ?
C33 C32 C31 122.05(19) . . ?
C33 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
C34 C33 C32 120.6(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C35 119.0(2) . . ?
C33 C34 H34 120.5 . . ?
C35 C34 H34 120.5 . . ?
C34 C35 C36 120.7(2) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C36 C31 121.7(2) . . ?
C35 C36 H36 119.2 . . ?
C31 C36 H36 119.2 . . ?
C38 C37 C42 118.07(18) . . ?
C38 C37 C5 123.21(19) . . ?
C42 C37 C5 118.69(18) . . ?
C39 C38 C37 120.8(2) . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C38 C39 C40 120.4(2) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C39 C40 C41 119.7(2) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C42 C41 C40 119.9(2) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C37 120.97(19) . . ?
C41 C42 H42 119.5 . . ?
C37 C42 H42 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 0.4(2) . . . . ?
C6 N1 N2 N3 176.55(15) . . . . ?
N1 N2 N3 C4 0.4(2) . . . . ?
N1 N2 N3 C18 174.64(15) . . . . ?
N2 N3 C4 C30 -179.78(17) . . . . ?
C18 N3 C4 C30 6.7(3) . . . . ?
N2 N3 C4 C5 -1.1(2) . . . . ?
C18 N3 C4 C5 -174.55(17) . . . . ?
N2 N1 C5 C4 -1.1(2) . . . . ?
C6 N1 C5 C4 -176.66(17) . . . . ?
N2 N1 C5 C37 166.94(17) . . . . ?
C6 N1 C5 C37 -8.6(3) . . . . ?
C30 C4 C5 N1 179.6(2) . . . . ?
N3 C4 C5 N1 1.2(2) . . . . ?
C30 C4 C5 C37 12.9(4) . . . . ?
N3 C4 C5 C37 -165.52(19) . . . . ?
N2 N1 C6 C11 -99.4(2) . . . . ?
C5 N1 C6 C11 76.1(3) . . . . ?
N2 N1 C6 C7 82.0(2) . . . . ?
C5 N1 C6 C7 -102.5(2) . . . . ?
C11 C6 C7 C8 -1.8(3) . . . . ?
N1 C6 C7 C8 176.70(17) . . . . ?
C11 C6 C7 C12 177.87(19) . . . . ?
N1 C6 C7 C12 -3.6(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C12 C7 C8 C9 -179.7(2) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
C8 C9 C10 C11 -1.0(4) . . . . ?
C9 C10 C11 C6 -0.7(3) . . . . ?
C9 C10 C11 C15 179.2(2) . . . . ?
C7 C6 C11 C10 2.2(3) . . . . ?
N1 C6 C11 C10 -176.37(18) . . . . ?
C7 C6 C11 C15 -177.78(19) . . . . ?
N1 C6 C11 C15 3.7(3) . . . . ?
C8 C7 C12 C14 -62.8(3) . . . . ?
C6 C7 C12 C14 117.5(2) . . . . ?
C8 C7 C12 C13 59.3(3) . . . . ?
C6 C7 C12 C13 -120.3(2) . . . . ?
C10 C11 C15 C16 -63.7(3) . . . . ?
C6 C11 C15 C16 116.3(2) . . . . ?
C10 C11 C15 C17 59.8(3) . . . . ?
C6 C11 C15 C17 -120.3(2) . . . . ?
N2 N3 C18 C19 -77.6(2) . . . . ?
C4 N3 C18 C19 95.8(2) . . . . ?
N2 N3 C18 C23 102.0(2) . . . . ?
C4 N3 C18 C23 -84.7(2) . . . . ?
C23 C18 C19 C20 -3.8(3) . . . . ?
N3 C18 C19 C20 175.74(17) . . . . ?
C23 C18 C19 C24 176.04(19) . . . . ?
N3 C18 C19 C24 -4.4(3) . . . . ?
C18 C19 C20 C21 1.1(3) . . . . ?
C24 C19 C20 C21 -178.7(2) . . . . ?
C19 C20 C21 C22 1.7(3) . . . . ?
C20 C21 C22 C23 -2.1(3) . . . . ?
C21 C22 C23 C18 -0.4(3) . . . . ?
C21 C22 C23 C27 179.79(19) . . . . ?
C19 C18 C23 C22 3.4(3) . . . . ?
N3 C18 C23 C22 -176.12(17) . . . . ?
C19 C18 C23 C27 -176.74(18) . . . . ?
N3 C18 C23 C27 3.7(3) . . . . ?
C20 C19 C24 C25 -33.9(5) . . . . ?
C18 C19 C24 C25 146.2(5) . . . . ?
C20 C19 C24 C26A 47.9(3) . . . . ?
C18 C19 C24 C26A -131.9(3) . . . . ?
C20 C19 C24 C25A -73.7(3) . . . . ?
C18 C19 C24 C25A 106.5(3) . . . . ?
C20 C19 C24 C26 90.8(4) . . . . ?
C18 C19 C24 C26 -89.1(4) . . . . ?
C22 C23 C27 C28 99.4(2) . . . . ?
C18 C23 C27 C28 -80.5(2) . . . . ?
C22 C23 C27 C29 -25.4(3) . . . . ?
C18 C23 C27 C29 154.78(18) . . . . ?
N3 C4 C30 C31 -164.9(2) . . . . ?
C5 C4 C30 C31 16.9(4) . . . . ?
C4 C30 C31 C36 16.3(4) . . . . ?
C4 C30 C31 C32 -166.9(2) . . . . ?
C36 C31 C32 C33 0.1(3) . . . . ?
C30 C31 C32 C33 -176.99(19) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C32 C33 C34 C35 0.8(3) . . . . ?
C33 C34 C35 C36 -0.4(3) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
C30 C31 C36 C35 177.1(2) . . . . ?
N1 C5 C37 C38 44.0(3) . . . . ?
C4 C5 C37 C38 -151.2(2) . . . . ?
N1 C5 C37 C42 -134.3(2) . . . . ?
C4 C5 C37 C42 30.5(3) . . . . ?
C42 C37 C38 C39 3.0(3) . . . . ?
C5 C37 C38 C39 -175.24(18) . . . . ?
C37 C38 C39 C40 -1.5(3) . . . . ?
C38 C39 C40 C41 -1.0(3) . . . . ?
C39 C40 C41 C42 1.8(3) . . . . ?
C40 C41 C42 C37 -0.2(3) . . . . ?
C38 C37 C42 C41 -2.2(3) . . . . ?
C5 C37 C42 C41 176.18(18) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_wl503
_database_code_depnum_ccdc_archive 'CCDC 2209654'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2023-03-24 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            'C24 H18 F N5 O'
_chemical_formula_weight         411.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.4361(5)
_cell_length_b                   10.9609(6)
_cell_length_c                   21.3387(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1973.13(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    18067
_cell_measurement_theta_min      3.414
_cell_measurement_theta_max      27.448

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_T_max  0.7154
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18067
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.414
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4442
_reflns_number_gt                3245
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.4184P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   .
_chemical_absolute_configuration .
_refine_ls_number_reflns         4442
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
N1 N 0.8411(3) 0.3516(2) 0.61739(12) 0.0278(6) Uani 1 1 d . . . . .
N2 N 0.8779(3) 0.2620(2) 0.65585(12) 0.0315(6) Uani 1 1 d . . . . .
N3 N 0.8432(3) 0.1621(2) 0.62313(12) 0.0301(7) Uani 1 1 d . . . . .
C4 C 0.7862(4) 0.1881(3) 0.56486(16) 0.0281(7) Uani 1 1 d . . . . .
C5 C 0.7830(4) 0.3116(3) 0.56180(16) 0.0275(7) Uani 1 1 d . . . . .
H5 H 0.757(4) 0.374(3) 0.5279(18) 0.038(10) Uiso 1 1 d . . . . .
C6 C 0.8898(4) 0.4746(3) 0.63330(14) 0.0263(7) Uani 1 1 d . . . . .
C7 C 1.0212(4) 0.4885(3) 0.67157(16) 0.0331(8) Uani 1 1 d . . . . .
H7 H 1.072795 0.419326 0.689023 0.040 Uiso 1 1 calc R U . . .
C8 C 1.0759(4) 0.6054(3) 0.68393(17) 0.0353(8) Uani 1 1 d . . . . .
H8 H 1.165612 0.618146 0.710017 0.042 Uiso 1 1 calc R U . . .
C9 C 0.9974(4) 0.7020(3) 0.65761(17) 0.0335(8) Uani 1 1 d . . . . .
C10 C 0.8682(4) 0.6887(3) 0.61946(16) 0.0340(8) Uani 1 1 d . . . . .
H10 H 0.817366 0.758248 0.602053 0.041 Uiso 1 1 calc R U . . .
C11 C 0.8122(4) 0.5722(3) 0.60652(15) 0.0301(8) Uani 1 1 d . . . . .
H11 H 0.723132 0.560158 0.580005 0.036 Uiso 1 1 calc R U . . .
F12 F 1.0516(3) 0.81606(18) 0.67015(11) 0.0513(6) Uani 1 1 d . . . . .
C13 C 0.8712(6) 0.0427(3) 0.65120(18) 0.0494(11) Uani 1 1 d . . . . .
H13A H 0.915852 -0.012463 0.619647 0.074 Uiso 1 1 calc R U . . .
H13B H 0.770758 0.009273 0.666651 0.074 Uiso 1 1 calc R U . . .
H13C H 0.945743 0.050946 0.686160 0.074 Uiso 1 1 calc R U . . .
C14 C 0.7536(4) 0.0923(3) 0.51633(16) 0.0300(8) Uani 1 1 d . . . . .
N15 N 0.9024(3) 0.0160(3) 0.50667(14) 0.0332(7) Uani 1 1 d . . . . .
N16 N 0.9462(3) 0.0296(2) 0.45029(14) 0.0324(7) Uani 1 1 d . . . . .
C17 C 0.8528(4) 0.1103(3) 0.41525(16) 0.0315(8) Uani 1 1 d . . . . .
C18 C 0.7318(4) 0.1577(3) 0.45292(16) 0.0305(8) Uani 1 1 d . . . . .
O19 O 0.6273(3) 0.2347(2) 0.44343(11) 0.0342(6) Uani 1 1 d . . . . .
C20 C 0.6133(4) 0.0111(3) 0.53289(14) 0.0260(7) Uani 1 1 d . . . . .
C21 C 0.4793(4) 0.0586(3) 0.56181(16) 0.0337(8) Uani 1 1 d . . . . .
H21 H 0.474974 0.142898 0.572075 0.040 Uiso 1 1 calc R U . . .
C22 C 0.3524(5) -0.0161(3) 0.57567(17) 0.0411(9) Uani 1 1 d . . . . .
H22 H 0.260391 0.017492 0.594712 0.049 Uiso 1 1 calc R U . . .
C23 C 0.3579(5) -0.1390(3) 0.56213(16) 0.0396(9) Uani 1 1 d . . . . .
H23 H 0.271075 -0.190212 0.572683 0.048 Uiso 1 1 calc R U . . .
C24 C 0.4899(5) -0.1873(3) 0.53322(17) 0.0375(9) Uani 1 1 d . . . . .
H24 H 0.493827 -0.271822 0.523492 0.045 Uiso 1 1 calc R U . . .
C25 C 0.6166(4) -0.1127(3) 0.51840(17) 0.0324(8) Uani 1 1 d . . . . .
H25 H 0.706905 -0.146277 0.498125 0.039 Uiso 1 1 calc R U . . .
C26 C 0.8878(4) 0.1382(3) 0.34929(16) 0.0314(8) Uani 1 1 d . . . . .
C27 C 0.9870(5) 0.0636(4) 0.31383(17) 0.0454(10) Uani 1 1 d . . . . .
H27 H 1.033690 -0.006504 0.332403 0.054 Uiso 1 1 calc R U . . .
C28 C 1.0181(6) 0.0912(5) 0.2513(2) 0.0654(14) Uani 1 1 d . . . . .
H28 H 1.086822 0.040364 0.227620 0.078 Uiso 1 1 calc R U . . .
C29 C 0.9492(6) 0.1924(5) 0.2235(2) 0.0602(12) Uani 1 1 d . . . . .
H29 H 0.970655 0.211563 0.180940 0.072 Uiso 1 1 calc R U . . .
C30 C 0.8507(5) 0.2639(4) 0.25792(17) 0.0501(10) Uani 1 1 d . . . . .
H30 H 0.802043 0.332637 0.238802 0.060 Uiso 1 1 calc R U . . .
C31 C 0.8199(4) 0.2388(3) 0.31990(17) 0.0386(9) Uani 1 1 d . . . . .
H31 H 0.751271 0.290849 0.342966 0.046 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
N1 N2 1.317(4) . ?
N1 C5 1.357(4) . ?
N1 C6 1.449(4) . ?
N2 N3 1.332(4) . ?
N3 C4 1.363(4) . ?
N3 C13 1.459(4) . ?
C4 C5 1.355(5) . ?
C4 C14 1.500(5) . ?
C5 H5 1.02(4) . ?
C6 C11 1.378(5) . ?
C6 C7 1.385(5) . ?
C7 C8 1.388(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.369(5) . ?
C8 H8 0.9500 . ?
C9 F12 1.357(4) . ?
C9 C10 1.368(5) . ?
C10 C11 1.389(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N15 1.522(4) . ?
C14 C20 1.522(5) . ?
C14 C18 1.542(5) . ?
N15 N16 1.267(4) . ?
N16 C17 1.401(4) . ?
C17 C18 1.399(5) . ?
C17 C26 1.470(5) . ?
C18 O19 1.237(4) . ?
C20 C21 1.390(5) . ?
C20 C25 1.392(4) . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C31 1.392(5) . ?
C26 C27 1.394(5) . ?
C27 C28 1.393(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(6) . ?
C28 H28 0.9500 . ?
C29 C30 1.358(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 112.9(3) . . ?
N2 N1 C6 118.7(3) . . ?
C5 N1 C6 127.5(3) . . ?
N1 N2 N3 103.6(2) . . ?
N2 N3 C4 112.5(3) . . ?
N2 N3 C13 119.2(3) . . ?
C4 N3 C13 128.3(3) . . ?
C5 C4 N3 105.1(3) . . ?
C5 C4 C14 131.5(3) . . ?
N3 C4 C14 123.2(3) . . ?
C4 C5 N1 105.9(3) . . ?
C4 C5 H5 135(2) . . ?
N1 C5 H5 119(2) . . ?
C11 C6 C7 122.6(3) . . ?
C11 C6 N1 119.3(3) . . ?
C7 C6 N1 117.9(3) . . ?
C6 C7 C8 118.7(3) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C9 C8 C7 118.4(3) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
F12 C9 C10 118.9(3) . . ?
F12 C9 C8 117.9(3) . . ?
C10 C9 C8 123.1(3) . . ?
C9 C10 C11 119.1(3) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C6 C11 C10 118.0(3) . . ?
C6 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C4 C14 N15 109.1(3) . . ?
C4 C14 C20 113.0(3) . . ?
N15 C14 C20 110.6(3) . . ?
C4 C14 C18 107.6(3) . . ?
N15 C14 C18 103.6(3) . . ?
C20 C14 C18 112.5(3) . . ?
N16 N15 C14 107.7(3) . . ?
N15 N16 C17 114.7(3) . . ?
C18 C17 N16 109.8(3) . . ?
C18 C17 C26 128.2(3) . . ?
N16 C17 C26 122.0(3) . . ?
O19 C18 C17 132.8(3) . . ?
O19 C18 C14 123.1(3) . . ?
C17 C18 C14 104.1(3) . . ?
C21 C20 C25 118.7(3) . . ?
C21 C20 C14 121.1(3) . . ?
C25 C20 C14 120.2(3) . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.6(3) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.7(3) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
C31 C26 C27 117.9(3) . . ?
C31 C26 C17 120.9(3) . . ?
C27 C26 C17 121.2(3) . . ?
C28 C27 C26 120.4(4) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 120.3(4) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 119.2(4) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C29 C30 C31 121.3(4) . . ?
C29 C30 H30 119.3 . . ?
C31 C30 H30 119.3 . . ?
C30 C31 C26 120.9(4) . . ?
C30 C31 H31 119.5 . . ?
C26 C31 H31 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 0.6(3) . . . . ?
C6 N1 N2 N3 -169.2(3) . . . . ?
N1 N2 N3 C4 0.3(3) . . . . ?
N1 N2 N3 C13 179.2(3) . . . . ?
N2 N3 C4 C5 -1.1(4) . . . . ?
C13 N3 C4 C5 -179.9(4) . . . . ?
N2 N3 C4 C14 173.6(3) . . . . ?
C13 N3 C4 C14 -5.2(6) . . . . ?
N3 C4 C5 N1 1.3(4) . . . . ?
C14 C4 C5 N1 -172.8(3) . . . . ?
N2 N1 C5 C4 -1.2(4) . . . . ?
C6 N1 C5 C4 167.4(3) . . . . ?
N2 N1 C6 C11 -159.0(3) . . . . ?
C5 N1 C6 C11 32.9(5) . . . . ?
N2 N1 C6 C7 25.7(4) . . . . ?
C5 N1 C6 C7 -142.4(3) . . . . ?
C11 C6 C7 C8 0.6(5) . . . . ?
N1 C6 C7 C8 175.8(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C7 C8 C9 F12 179.8(3) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
F12 C9 C10 C11 -180.0(3) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C7 C6 C11 C10 -0.8(5) . . . . ?
N1 C6 C11 C10 -175.9(3) . . . . ?
C9 C10 C11 C6 0.4(5) . . . . ?
C5 C4 C14 N15 118.9(4) . . . . ?
N3 C4 C14 N15 -54.3(4) . . . . ?
C5 C4 C14 C20 -117.7(4) . . . . ?
N3 C4 C14 C20 69.2(4) . . . . ?
C5 C4 C14 C18 7.1(5) . . . . ?
N3 C4 C14 C18 -166.0(3) . . . . ?
C4 C14 N15 N16 -117.8(3) . . . . ?
C20 C14 N15 N16 117.3(3) . . . . ?
C18 C14 N15 N16 -3.5(3) . . . . ?
C14 N15 N16 C17 2.0(4) . . . . ?
N15 N16 C17 C18 0.6(4) . . . . ?
N15 N16 C17 C26 179.1(3) . . . . ?
N16 C17 C18 O19 176.2(3) . . . . ?
C26 C17 C18 O19 -2.2(6) . . . . ?
N16 C17 C18 C14 -2.7(4) . . . . ?
C26 C17 C18 C14 178.8(3) . . . . ?
C4 C14 C18 O19 -60.0(4) . . . . ?
N15 C14 C18 O19 -175.5(3) . . . . ?
C20 C14 C18 O19 65.1(4) . . . . ?
C4 C14 C18 C17 119.1(3) . . . . ?
N15 C14 C18 C17 3.6(3) . . . . ?
C20 C14 C18 C17 -115.8(3) . . . . ?
C4 C14 C20 C21 37.9(4) . . . . ?
N15 C14 C20 C21 160.5(3) . . . . ?
C18 C14 C20 C21 -84.2(4) . . . . ?
C4 C14 C20 C25 -143.0(3) . . . . ?
N15 C14 C20 C25 -20.4(4) . . . . ?
C18 C14 C20 C25 94.9(4) . . . . ?
C25 C20 C21 C22 -0.1(5) . . . . ?
C14 C20 C21 C22 179.1(3) . . . . ?
C20 C21 C22 C23 1.2(6) . . . . ?
C21 C22 C23 C24 -1.4(6) . . . . ?
C22 C23 C24 C25 0.5(5) . . . . ?
C23 C24 C25 C20 0.6(5) . . . . ?
C21 C20 C25 C24 -0.8(5) . . . . ?
C14 C20 C25 C24 180.0(3) . . . . ?
C18 C17 C26 C31 14.1(5) . . . . ?
N16 C17 C26 C31 -164.2(3) . . . . ?
C18 C17 C26 C27 -164.5(4) . . . . ?
N16 C17 C26 C27 17.2(5) . . . . ?
C31 C26 C27 C28 1.0(6) . . . . ?
C17 C26 C27 C28 179.7(4) . . . . ?
C26 C27 C28 C29 -0.7(7) . . . . ?
C27 C28 C29 C30 -0.3(7) . . . . ?
C28 C29 C30 C31 1.0(7) . . . . ?
C29 C30 C31 C26 -0.6(6) . . . . ?
C27 C26 C31 C30 -0.4(6) . . . . ?
C17 C26 C31 C30 -179.0(3) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_wl589
_database_code_depnum_ccdc_archive 'CCDC 2209656'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2023-03-24 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            'C30 H34 N5 O2'
_chemical_formula_weight         496.62

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                   9.4016(11)
_cell_length_b                   9.7932(8)
_cell_length_c                   14.9499(17)
_cell_angle_alpha                100.871(3)
_cell_angle_beta                 101.457(3)
_cell_angle_gamma                92.165(3)
_cell_volume                     1320.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    39187
_cell_measurement_theta_min      1.419
_cell_measurement_theta_max      27.471

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             530
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6781
_exptl_absorpt_correction_T_max  0.7400
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39187
_diffrn_reflns_av_unetI/netI     0.0893
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.419
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6025
_reflns_number_gt                3989
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.1687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6025
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.007
_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
N1 N 0.58067(16) 0.54363(16) 0.74208(10) 0.0219(4) Uani 1 1 d . . . . .
N2 N 0.64877(17) 0.42747(16) 0.74288(11) 0.0242(4) Uani 1 1 d . . . . .
N3 N 0.70092(17) 0.41023(15) 0.66606(11) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.66871(19) 0.51300(18) 0.61626(13) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.5890(2) 0.5996(2) 0.66732(13) 0.0218(4) Uani 1 1 d . . . . .
H5 H 0.545(2) 0.683(2) 0.6588(14) 0.034(6) Uiso 1 1 d . . . . .
C6 C 0.5177(2) 0.5991(2) 0.82101(13) 0.0222(4) Uani 1 1 d . . . . .
C7 C 0.4091(2) 0.5185(2) 0.84298(14) 0.0252(4) Uani 1 1 d . . . . .
C8 C 0.3590(2) 0.5737(2) 0.92298(14) 0.0288(5) Uani 1 1 d . . . . .
H8 H 0.286215 0.520533 0.940470 0.035 Uiso 1 1 calc R U . . .
C9 C 0.4111(2) 0.7030(2) 0.97797(13) 0.0265(5) Uani 1 1 d . . . . .
C10 C 0.5160(2) 0.7802(2) 0.95098(14) 0.0278(5) Uani 1 1 d . . . . .
H10 H 0.550828 0.869923 0.987328 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5721(2) 0.7309(2) 0.87266(13) 0.0245(4) Uani 1 1 d . . . . .
C12 C 0.3427(2) 0.3805(2) 0.78397(15) 0.0350(5) Uani 1 1 d . . . . .
H12A H 0.359377 0.373720 0.720670 0.052 Uiso 1 1 calc R U . . .
H12B H 0.237848 0.373174 0.781922 0.052 Uiso 1 1 calc R U . . .
H12C H 0.387724 0.304702 0.810873 0.052 Uiso 1 1 calc R U . . .
C13 C 0.3524(2) 0.7611(2) 1.06270(15) 0.0381(5) Uani 1 1 d . . . . .
H13A H 0.261175 0.803193 1.043659 0.057 Uiso 1 1 calc R U . . .
H13B H 0.423526 0.832186 1.104805 0.057 Uiso 1 1 calc R U . . .
H13C H 0.334212 0.685803 1.094831 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6833(2) 0.8206(2) 0.84565(14) 0.0313(5) Uani 1 1 d . . . . .
H14A H 0.755193 0.762098 0.821773 0.047 Uiso 1 1 calc R U . . .
H14B H 0.732404 0.890064 0.900340 0.047 Uiso 1 1 calc R U . . .
H14C H 0.634901 0.868206 0.797245 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7913(2) 0.2938(2) 0.64807(15) 0.0307(5) Uani 1 1 d . . . . .
H15A H 0.743794 0.229206 0.590562 0.046 Uiso 1 1 calc R U . . .
H15B H 0.804106 0.244833 0.700199 0.046 Uiso 1 1 calc R U . . .
H15C H 0.886664 0.329580 0.641412 0.046 Uiso 1 1 calc R U . . .
C16 C 0.7137(2) 0.52239(18) 0.53018(13) 0.0201(4) Uani 1 1 d . . . . .
N17 N 0.73275(17) 0.40484(16) 0.47751(11) 0.0219(4) Uani 1 1 d . . . . .
N18 N 0.76878(19) 0.41003(17) 0.39641(11) 0.0258(4) Uani 1 1 d . . . . .
H18 H 0.808(3) 0.494(3) 0.3870(17) 0.055(7) Uiso 1 1 d . . . . .
C19 C 0.7943(2) 0.29154(19) 0.33302(13) 0.0207(4) Uani 1 1 d . . . . .
C20 C 0.6978(2) 0.17057(19) 0.30657(13) 0.0228(4) Uani 1 1 d . . . . .
C21 C 0.7246(2) 0.0565(2) 0.22977(14) 0.0257(4) Uani 1 1 d . . . . .
H21A H 0.652148 0.059903 0.172427 0.031 Uiso 1 1 calc R U . . .
H21B H 0.705356 -0.034203 0.246924 0.031 Uiso 1 1 calc R U . . .
C22 C 0.8756(2) 0.0593(2) 0.20642(13) 0.0248(4) Uani 1 1 d . . . . .
C23 C 0.9217(2) 0.2090(2) 0.20296(13) 0.0255(4) Uani 1 1 d . . . . .
H23A H 1.025432 0.214045 0.198629 0.031 Uiso 1 1 calc R U . . .
H23B H 0.864539 0.232037 0.145338 0.031 Uiso 1 1 calc R U . . .
C24 C 0.9033(2) 0.31858(19) 0.28470(13) 0.0221(4) Uani 1 1 d . . . . .
O25 O 0.58788(15) 0.15268(14) 0.34075(10) 0.0296(3) Uani 1 1 d . . . . .
O26 O 0.97937(15) 0.43227(14) 0.30390(10) 0.0310(4) Uani 1 1 d . . . . .
C27 C 0.9865(2) 0.0064(2) 0.27900(14) 0.0318(5) Uani 1 1 d . . . . .
H27A H 0.955987 -0.089725 0.280730 0.048 Uiso 1 1 calc R U . . .
H27B H 0.992495 0.065848 0.340403 0.048 Uiso 1 1 calc R U . . .
H27C H 1.082176 0.009077 0.262408 0.048 Uiso 1 1 calc R U . . .
C28 C 0.8691(3) -0.0334(2) 0.11099(14) 0.0366(5) Uani 1 1 d . . . . .
H28A H 0.802835 0.003066 0.063313 0.055 Uiso 1 1 calc R U . . .
H28B H 0.833774 -0.128621 0.111455 0.055 Uiso 1 1 calc R U . . .
H28C H 0.966663 -0.034011 0.097019 0.055 Uiso 1 1 calc R U . . .
C29 C 0.7327(2) 0.66186(19) 0.50592(12) 0.0201(4) Uani 1 1 d . . . . .
C30 C 0.8694(2) 0.70806(19) 0.49493(13) 0.0230(4) Uani 1 1 d . . . . .
H30 H 0.949917 0.653675 0.507190 0.028 Uiso 1 1 calc R U . . .
C31 C 0.8880(2) 0.8324(2) 0.46635(14) 0.0278(5) Uani 1 1 d . . . . .
H31 H 0.981215 0.863013 0.458851 0.033 Uiso 1 1 calc R U . . .
C32 C 0.7716(2) 0.9125(2) 0.44858(14) 0.0309(5) Uani 1 1 d . . . . .
H32 H 0.784667 0.997463 0.428174 0.037 Uiso 1 1 calc R U . . .
C33 C 0.6364(2) 0.8689(2) 0.46055(14) 0.0293(5) Uani 1 1 d . . . . .
H33 H 0.556711 0.924458 0.448696 0.035 Uiso 1 1 calc R U . . .
C34 C 0.6161(2) 0.7446(2) 0.48978(13) 0.0255(4) Uani 1 1 d . . . . .
H34 H 0.523229 0.715805 0.498783 0.031 Uiso 1 1 calc R U . . .
C35 C 1.0347(2) 0.4764(2) 0.09003(15) 0.0325(5) Uani 1 1 d . . . . .
H35 H 1.058718 0.460208 0.151738 0.039 Uiso 1 1 calc R U . . .
C36 C 1.0365(2) 0.3705(2) 0.01535(15) 0.0339(5) Uani 1 1 d . . . . .
H36 H 1.061576 0.280865 0.025695 0.041 Uiso 1 1 calc R U . . .
C37 C 1.0022(2) 0.3936(2) -0.07461(15) 0.0325(5) Uani 1 1 d . . . . .
H37 H 1.003995 0.320037 -0.125780 0.039 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
N1 N2 1.327(2) . ?
N1 C5 1.348(2) . ?
N1 C6 1.448(2) . ?
N2 N3 1.321(2) . ?
N3 C4 1.369(2) . ?
N3 C15 1.464(2) . ?
C4 C5 1.377(3) . ?
C4 C16 1.449(3) . ?
C5 H5 0.95(2) . ?
C6 C11 1.393(3) . ?
C6 C7 1.394(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.504(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(3) . ?
C9 C13 1.504(3) . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C14 1.504(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N17 1.307(2) . ?
C16 C29 1.491(2) . ?
N17 N18 1.331(2) . ?
N18 C19 1.414(2) . ?
N18 H18 0.93(2) . ?
C19 C20 1.408(3) . ?
C19 C24 1.410(3) . ?
C20 O25 1.260(2) . ?
C20 C21 1.510(3) . ?
C21 C22 1.529(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.527(3) . ?
C22 C28 1.528(3) . ?
C22 C27 1.529(3) . ?
C23 C24 1.509(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O26 1.253(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C34 1.397(3) . ?
C29 C30 1.397(3) . ?
C30 C31 1.380(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.383(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.382(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.377(3) . ?
C35 C37 1.381(3) 2_765 ?
C35 H35 0.9500 . ?
C36 C37 1.383(3) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C5 112.88(15) . . ?
N2 N1 C6 118.53(14) . . ?
C5 N1 C6 128.43(16) . . ?
N3 N2 N1 103.73(13) . . ?
N2 N3 C4 113.24(15) . . ?
N2 N3 C15 118.05(14) . . ?
C4 N3 C15 128.55(16) . . ?
N3 C4 C5 104.12(16) . . ?
N3 C4 C16 125.40(16) . . ?
C5 C4 C16 130.48(16) . . ?
N1 C5 C4 106.02(16) . . ?
N1 C5 H5 121.0(12) . . ?
C4 C5 H5 132.9(12) . . ?
C11 C6 C7 123.23(18) . . ?
C11 C6 N1 117.54(16) . . ?
C7 C6 N1 119.22(17) . . ?
C6 C7 C8 116.64(19) . . ?
C6 C7 C12 123.53(18) . . ?
C8 C7 C12 119.80(18) . . ?
C9 C8 C7 122.58(19) . . ?
C9 C8 H8 118.7 . . ?
C7 C8 H8 118.7 . . ?
C8 C9 C10 118.10(18) . . ?
C8 C9 C13 121.32(19) . . ?
C10 C9 C13 120.5(2) . . ?
C9 C10 C11 122.4(2) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C6 117.04(17) . . ?
C10 C11 C14 119.97(18) . . ?
C6 C11 C14 122.96(17) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N17 C16 C4 116.57(16) . . ?
N17 C16 C29 124.07(16) . . ?
C4 C16 C29 119.35(16) . . ?
C16 N17 N18 117.82(15) . . ?
N17 N18 C19 123.94(16) . . ?
N17 N18 H18 119.6(15) . . ?
C19 N18 H18 113.7(15) . . ?
C20 C19 C24 123.45(17) . . ?
C20 C19 N18 121.93(17) . . ?
C24 C19 N18 113.10(16) . . ?
O25 C20 C19 124.40(18) . . ?
O25 C20 C21 117.69(17) . . ?
C19 C20 C21 117.88(16) . . ?
C20 C21 C22 117.39(16) . . ?
C20 C21 H21A 108.0 . . ?
C22 C21 H21A 108.0 . . ?
C20 C21 H21B 108.0 . . ?
C22 C21 H21B 108.0 . . ?
H21A C21 H21B 107.2 . . ?
C23 C22 C28 108.94(16) . . ?
C23 C22 C27 110.08(16) . . ?
C28 C22 C27 108.78(16) . . ?
C23 C22 C21 108.36(15) . . ?
C28 C22 C21 109.55(17) . . ?
C27 C22 C21 111.11(16) . . ?
C24 C23 C22 115.52(15) . . ?
C24 C23 H23A 108.4 . . ?
C22 C23 H23A 108.4 . . ?
C24 C23 H23B 108.4 . . ?
C22 C23 H23B 108.4 . . ?
H23A C23 H23B 107.5 . . ?
O26 C24 C19 122.57(18) . . ?
O26 C24 C23 119.15(17) . . ?
C19 C24 C23 118.16(16) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C22 C28 H28A 109.5 . . ?
C22 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C22 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C34 C29 C30 119.18(17) . . ?
C34 C29 C16 121.77(17) . . ?
C30 C29 C16 118.98(16) . . ?
C31 C30 C29 120.29(18) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.33(18) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 119.89(18) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 120.46(18) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C33 C34 C29 119.82(18) . . ?
C33 C34 H34 120.1 . . ?
C29 C34 H34 120.1 . . ?
C36 C35 C37 119.52(19) . 2_765 ?
C36 C35 H35 120.2 . . ?
C37 C35 H35 120.2 2_765 . ?
C35 C36 C37 120.51(19) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C35 C37 C36 120.0(2) 2_765 . ?
C35 C37 H37 120.0 2_765 . ?
C36 C37 H37 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 N2 N3 -0.2(2) . . . . ?
C6 N1 N2 N3 -175.96(15) . . . . ?
N1 N2 N3 C4 0.4(2) . . . . ?
N1 N2 N3 C15 176.33(16) . . . . ?
N2 N3 C4 C5 -0.4(2) . . . . ?
C15 N3 C4 C5 -175.87(18) . . . . ?
N2 N3 C4 C16 178.93(17) . . . . ?
C15 N3 C4 C16 3.5(3) . . . . ?
N2 N1 C5 C4 -0.1(2) . . . . ?
C6 N1 C5 C4 175.18(17) . . . . ?
N3 C4 C5 N1 0.3(2) . . . . ?
C16 C4 C5 N1 -179.03(19) . . . . ?
N2 N1 C6 C11 117.70(19) . . . . ?
C5 N1 C6 C11 -57.4(3) . . . . ?
N2 N1 C6 C7 -61.0(2) . . . . ?
C5 N1 C6 C7 124.0(2) . . . . ?
C11 C6 C7 C8 -2.4(3) . . . . ?
N1 C6 C7 C8 176.18(16) . . . . ?
C11 C6 C7 C12 175.68(18) . . . . ?
N1 C6 C7 C12 -5.7(3) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C12 C7 C8 C9 -177.09(18) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C7 C8 C9 C13 178.59(18) . . . . ?
C8 C9 C10 C11 -1.5(3) . . . . ?
C13 C9 C10 C11 -179.33(18) . . . . ?
C9 C10 C11 C6 0.3(3) . . . . ?
C9 C10 C11 C14 178.68(18) . . . . ?
C7 C6 C11 C10 1.8(3) . . . . ?
N1 C6 C11 C10 -176.85(16) . . . . ?
C7 C6 C11 C14 -176.57(18) . . . . ?
N1 C6 C11 C14 4.8(3) . . . . ?
N3 C4 C16 N17 28.8(3) . . . . ?
C5 C4 C16 N17 -152.0(2) . . . . ?
N3 C4 C16 C29 -152.36(18) . . . . ?
C5 C4 C16 C29 26.9(3) . . . . ?
C4 C16 N17 N18 177.55(16) . . . . ?
C29 C16 N17 N18 -1.3(3) . . . . ?
C16 N17 N18 C19 179.30(17) . . . . ?
N17 N18 C19 C20 48.0(3) . . . . ?
N17 N18 C19 C24 -145.66(18) . . . . ?
C24 C19 C20 O25 -170.11(17) . . . . ?
N18 C19 C20 O25 -5.2(3) . . . . ?
C24 C19 C20 C21 7.7(3) . . . . ?
N18 C19 C20 C21 172.64(16) . . . . ?
O25 C20 C21 C22 -164.19(16) . . . . ?
C19 C20 C21 C22 17.9(2) . . . . ?
C20 C21 C22 C23 -44.3(2) . . . . ?
C20 C21 C22 C28 -163.02(16) . . . . ?
C20 C21 C22 C27 76.8(2) . . . . ?
C28 C22 C23 C24 167.74(16) . . . . ?
C27 C22 C23 C24 -73.1(2) . . . . ?
C21 C22 C23 C24 48.6(2) . . . . ?
C20 C19 C24 O26 173.23(17) . . . . ?
N18 C19 C24 O26 7.1(3) . . . . ?
C20 C19 C24 C23 -2.8(3) . . . . ?
N18 C19 C24 C23 -168.97(16) . . . . ?
C22 C23 C24 O26 156.45(17) . . . . ?
C22 C23 C24 C19 -27.3(2) . . . . ?
N17 C16 C29 C34 115.3(2) . . . . ?
C4 C16 C29 C34 -63.5(2) . . . . ?
N17 C16 C29 C30 -61.8(3) . . . . ?
C4 C16 C29 C30 119.43(19) . . . . ?
C34 C29 C30 C31 -1.5(3) . . . . ?
C16 C29 C30 C31 175.61(17) . . . . ?
C29 C30 C31 C32 0.2(3) . . . . ?
C30 C31 C32 C33 0.8(3) . . . . ?
C31 C32 C33 C34 -0.4(3) . . . . ?
C32 C33 C34 C29 -0.9(3) . . . . ?
C30 C29 C34 C33 1.9(3) . . . . ?
C16 C29 C34 C33 -175.16(18) . . . . ?
C37 C35 C36 C37 0.2(4) 2_765 . . . ?
C35 C36 C37 C35 -0.2(4) . . . 2_765 ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_wl591
_database_code_depnum_ccdc_archive 'CCDC 2243057'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 downloaded from the CCDC.
;

_vrf_RINTA01_wl591               
;
RESPONSE:
weakly diffracting crysal
;

_vrf_PLAT020_wl591               
;
RESPONSE:
weakly diffracting crysal
;

_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            'C37 H46 N4 O2'
_chemical_formula_weight         578.78

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                   10.384(8)
_cell_length_b                   10.769(8)
_cell_length_c                   16.438(12)
_cell_angle_alpha                72.09(3)
_cell_angle_beta                 75.72(3)
_cell_angle_gamma                82.68(2)
_cell_volume                     1692(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    36009
_cell_measurement_theta_min      1.334
_cell_measurement_theta_max      27.728

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4549
_exptl_absorpt_correction_T_max  0.7011
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36009
_diffrn_reflns_av_unetI/netI     0.2390
_diffrn_reflns_av_R_equivalents  0.1895
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.334
_diffrn_reflns_theta_max         27.728
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7844
_reflns_number_gt                3526
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1126P)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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.061(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7844
_refine_ls_number_parameters     463
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.2259
_refine_ls_R_factor_gt           0.1143
_refine_ls_wR_factor_ref         0.3231
_refine_ls_wR_factor_gt          0.2631
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.994
_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
N1 N 0.7711(3) 0.1914(3) 0.61267(19) 0.0367(7) Uani 1 1 d . . . . .
C2 C 0.7237(3) 0.2517(3) 0.6765(2) 0.0331(8) Uani 1 1 d . . . . .
N3 N 0.6724(3) 0.1562(3) 0.7500(2) 0.0373(7) Uani 1 1 d . . . . .
C4 C 0.6949(4) 0.0373(3) 0.7316(3) 0.0443(10) Uani 1 1 d . . . . .
H4 H 0.671678 -0.045314 0.771964 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7542(4) 0.0590(3) 0.6483(3) 0.0445(10) Uani 1 1 d . . . . .
H5 H 0.780759 -0.005383 0.617961 0.053 Uiso 1 1 calc R U . . .
C6 C 0.8397(3) 0.2525(3) 0.5248(2) 0.0355(8) Uani 1 1 d . . . . .
C7 C 0.9775(4) 0.2585(4) 0.5055(3) 0.0456(10) Uani 1 1 d . . . . .
C8 C 1.0405(4) 0.3133(4) 0.4200(3) 0.0584(12) Uani 1 1 d . . . . .
H8 H 1.134539 0.317632 0.405326 0.070 Uiso 1 1 calc R U . . .
C9 C 0.9696(5) 0.3621(5) 0.3551(3) 0.0644(13) Uani 1 1 d . . . . .
H9 H 1.014636 0.399464 0.296197 0.077 Uiso 1 1 calc R U . . .
C10 C 0.8341(5) 0.3563(4) 0.3759(3) 0.0567(11) Uani 1 1 d . . . . .
H10 H 0.786414 0.390411 0.330603 0.068 Uiso 1 1 calc R U . . .
C11 C 0.7640(4) 0.3027(3) 0.4605(2) 0.0407(9) Uani 1 1 d . . . . .
C12 C 1.0568(4) 0.2072(4) 0.5770(3) 0.0561(11) Uani 1 1 d . . . . .
H12 H 0.992605 0.180668 0.634891 0.067 Uiso 1 1 calc R U . . .
C13 C 1.1405(5) 0.3119(5) 0.5785(4) 0.0840(17) Uani 1 1 d . . . . .
H13A H 1.212209 0.330370 0.525711 0.126 Uiso 1 1 calc R U . . .
H13B H 1.178992 0.281222 0.630546 0.126 Uiso 1 1 calc R U . . .
H13C H 1.084400 0.391840 0.580386 0.126 Uiso 1 1 calc R U . . .
C14 C 1.1454(5) 0.0868(5) 0.5639(4) 0.0884(18) Uani 1 1 d . . . . .
H14A H 1.091261 0.022652 0.558590 0.133 Uiso 1 1 calc R U . . .
H14B H 1.186653 0.047990 0.614218 0.133 Uiso 1 1 calc R U . . .
H14C H 1.214942 0.112734 0.510330 0.133 Uiso 1 1 calc R U . . .
C15 C 0.6136(4) 0.2994(4) 0.4831(3) 0.0510(11) Uani 1 1 d . . . . .
H15 H 0.581534 0.309109 0.543537 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5476(5) 0.4108(5) 0.4222(3) 0.0744(15) Uani 1 1 d . . . . .
H16A H 0.569417 0.398989 0.363422 0.112 Uiso 1 1 calc R U . . .
H16B H 0.580016 0.493967 0.419361 0.112 Uiso 1 1 calc R U . . .
H16C H 0.450946 0.411494 0.444327 0.112 Uiso 1 1 calc R U . . .
C17 C 0.5693(4) 0.1703(5) 0.4848(4) 0.0732(14) Uani 1 1 d . . . . .
H17A H 0.608040 0.152838 0.428426 0.110 Uiso 1 1 calc R U . . .
H17B H 0.472032 0.173743 0.495377 0.110 Uiso 1 1 calc R U . . .
H17C H 0.599243 0.100363 0.531798 0.110 Uiso 1 1 calc R U . . .
C18 C 0.6186(3) 0.1674(3) 0.8371(2) 0.0354(9) Uani 1 1 d . . . . .
C19 C 0.4824(3) 0.1997(3) 0.8616(2) 0.0366(9) Uani 1 1 d . . . . .
C20 C 0.4334(4) 0.2008(4) 0.9471(3) 0.0481(10) Uani 1 1 d . . . . .
H20 H 0.340847 0.219326 0.966106 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5151(4) 0.1758(4) 1.0072(3) 0.0489(10) Uani 1 1 d . . . . .
H21 H 0.478973 0.177136 1.066005 0.059 Uiso 1 1 calc R U . . .
C22 C 0.6494(4) 0.1490(4) 0.9790(3) 0.0506(11) Uani 1 1 d . . . . .
H22 H 0.706271 0.133728 1.018772 0.061 Uiso 1 1 calc R U . . .
C23 C 0.7033(4) 0.1439(4) 0.8943(3) 0.0433(10) Uani 1 1 d . . . . .
C24 C 0.3940(4) 0.2289(4) 0.7962(3) 0.0471(10) Uani 1 1 d . . . . .
H24 H 0.452035 0.257145 0.736080 0.057 Uiso 1 1 calc R U . . .
C25 C 0.2901(4) 0.3395(4) 0.8064(3) 0.0690(14) Uani 1 1 d . . . . .
H25A H 0.247838 0.367260 0.756119 0.104 Uiso 1 1 calc R U . . .
H25B H 0.333161 0.413367 0.809402 0.104 Uiso 1 1 calc R U . . .
H25C H 0.222517 0.308966 0.860434 0.104 Uiso 1 1 calc R U . . .
C26 C 0.3269(5) 0.1100(4) 0.8027(3) 0.0729(15) Uani 1 1 d . . . . .
H26A H 0.277795 0.129988 0.755958 0.109 Uiso 1 1 calc R U . . .
H26B H 0.264976 0.083299 0.859794 0.109 Uiso 1 1 calc R U . . .
H26C H 0.394067 0.038794 0.796609 0.109 Uiso 1 1 calc R U . . .
C27 C 0.8518(4) 0.1189(4) 0.8642(3) 0.0559(11) Uani 1 1 d . . . . .
H27 H 0.869886 0.121443 0.801094 0.067 Uiso 1 1 calc R U . . .
C28 C 0.9284(5) 0.2248(6) 0.8704(5) 0.112(2) Uani 1 1 d . . . . .
H28A H 1.022990 0.211774 0.844564 0.168 Uiso 1 1 calc R U . . .
H28B H 0.917549 0.220716 0.932134 0.168 Uiso 1 1 calc R U . . .
H28C H 0.894367 0.310431 0.838692 0.168 Uiso 1 1 calc R U . . .
C29 C 0.9017(5) -0.0134(6) 0.9139(4) 0.0921(18) Uani 1 1 d . . . . .
H29A H 0.852303 -0.081342 0.908800 0.138 Uiso 1 1 calc R U . . .
H29B H 0.888607 -0.017567 0.975760 0.138 Uiso 1 1 calc R U . . .
H29C H 0.996673 -0.027212 0.889383 0.138 Uiso 1 1 calc R U . . .
C30 C 0.7272(3) 0.3844(3) 0.6657(2) 0.0345(8) Uani 1 1 d . . . . .
H30 H 0.764446 0.443387 0.610933 0.041 Uiso 1 1 calc R U . . .
N31 N 0.6747(3) 0.4246(3) 0.7373(2) 0.0459(8) Uani 1 1 d . . . . .
N32 N 0.6787(3) 0.5445(3) 0.7304(2) 0.0537(9) Uani 1 1 d . . . . .
C33 C 0.6345(10) 0.5562(10) 0.8242(9) 0.042(3) Uani 0.561(3) 1 d D . P A 1
H33 H 0.624194 0.466830 0.866633 0.051 Uiso 0.561(3) 1 calc R U P A 1
C34 C 0.7353(13) 0.6263(15) 0.8451(11) 0.044(3) Uani 0.561(3) 1 d D . P A 1
O35 O 0.7314(6) 0.7387(6) 0.8387(5) 0.0670(13) Uani 0.561(3) 1 d D . P A 1
O36 O 0.8346(5) 0.5431(5) 0.8692(4) 0.0636(17) Uani 0.561(3) 1 d D . P A 1
C37 C 0.9403(9) 0.5990(10) 0.8835(7) 0.075(2) Uani 0.561(3) 1 d D . P A 1
H37A H 1.016028 0.534935 0.888392 0.113 Uiso 0.561(3) 1 calc R U P A 1
H37B H 0.910700 0.624538 0.937765 0.113 Uiso 0.561(3) 1 calc R U P A 1
H37C H 0.967215 0.676323 0.834179 0.113 Uiso 0.561(3) 1 calc R U P A 1
C38 C 0.5021(7) 0.6283(8) 0.8272(6) 0.0450(19) Uani 0.561(3) 1 d D . P A 1
C39 C 0.4791(10) 0.7373(9) 0.7632(8) 0.0670(13) Uani 0.561(3) 1 d D . P A 1
H39 H 0.549331 0.769876 0.714331 0.080 Uiso 0.561(3) 1 calc R U P A 1
C40 C 0.3540(10) 0.8022(9) 0.7680(7) 0.079(3) Uani 0.561(3) 1 d D . P A 1
H40 H 0.338611 0.878577 0.722816 0.095 Uiso 0.561(3) 1 calc R U P A 1
C41 C 0.2519(11) 0.7542(14) 0.8396(8) 0.080(4) Uani 0.561(3) 1 d D . P A 1
H41 H 0.165324 0.795983 0.842157 0.097 Uiso 0.561(3) 1 calc R U P A 1
C42 C 0.2748(8) 0.6462(9) 0.9071(7) 0.080(3) Uani 0.561(3) 1 d D . P A 1
H42 H 0.206043 0.615579 0.957320 0.096 Uiso 0.561(3) 1 calc R U P A 1
C43 C 0.3989(7) 0.5841(8) 0.9000(6) 0.062(2) Uani 0.561(3) 1 d D . P A 1
H43 H 0.415265 0.509077 0.945780 0.074 Uiso 0.561(3) 1 calc R U P A 1
C33A C 0.5890(15) 0.5766(13) 0.8103(12) 0.042(3) Uani 0.439(3) 1 d D . P A 2
H33A H 0.539322 0.498353 0.848962 0.051 Uiso 0.439(3) 1 calc R U P A 2
C34A C 0.4927(13) 0.6921(11) 0.7882(12) 0.0670(13) Uani 0.439(3) 1 d D . P A 2
O35A O 0.5198(7) 0.8041(6) 0.7600(5) 0.0670(13) Uani 0.439(3) 1 d D . P A 2
O36A O 0.3681(6) 0.6590(7) 0.8088(6) 0.072(2) Uani 0.439(3) 1 d D . P A 2
C37A C 0.2727(15) 0.7681(18) 0.7871(12) 0.080(4) Uani 0.439(3) 1 d D . P A 2
H37D H 0.212737 0.745934 0.756712 0.121 Uiso 0.439(3) 1 calc R U P A 2
H37E H 0.320229 0.845431 0.748991 0.121 Uiso 0.439(3) 1 calc R U P A 2
H37F H 0.220902 0.786610 0.841029 0.121 Uiso 0.439(3) 1 calc R U P A 2
C38A C 0.6912(15) 0.6010(16) 0.8530(12) 0.041(4) Uani 0.439(3) 1 d D . P A 2
C39A C 0.7826(11) 0.6944(13) 0.8118(8) 0.047(3) Uani 0.439(3) 1 d D . P A 2
H39A H 0.780330 0.749566 0.754528 0.057 Uiso 0.439(3) 1 calc R U P A 2
C40A C 0.8787(9) 0.7083(11) 0.8536(8) 0.071(4) Uani 0.439(3) 1 d D . P A 2
H40A H 0.942362 0.772695 0.824814 0.085 Uiso 0.439(3) 1 calc R U P A 2
C41A C 0.8820(12) 0.6280(14) 0.9377(9) 0.075(2) Uani 0.439(3) 1 d D . P A 2
H41A H 0.949180 0.636193 0.965565 0.090 Uiso 0.439(3) 1 calc R U P A 2
C42A C 0.7896(11) 0.5383(11) 0.9798(8) 0.073(3) Uani 0.439(3) 1 d D . P A 2
H42A H 0.788351 0.486901 1.038454 0.088 Uiso 0.439(3) 1 calc R U P A 2
C43A C 0.6981(11) 0.5223(9) 0.9373(7) 0.065(3) Uani 0.439(3) 1 d D . P A 2
H43A H 0.637043 0.455390 0.965943 0.079 Uiso 0.439(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.359(4) . ?
N1 C5 1.381(4) . ?
N1 C6 1.433(4) . ?
C2 N3 1.364(4) . ?
C2 C30 1.389(5) . ?
N3 C4 1.383(5) . ?
N3 C18 1.438(5) . ?
C4 C5 1.316(5) . ?
C6 C7 1.393(5) . ?
C6 C11 1.406(5) . ?
C7 C8 1.374(6) . ?
C7 C12 1.525(5) . ?
C8 C9 1.378(6) . ?
C9 C10 1.369(6) . ?
C10 C11 1.382(5) . ?
C11 C15 1.517(5) . ?
C12 C13 1.519(6) . ?
C12 C14 1.531(6) . ?
C15 C17 1.509(6) . ?
C15 C16 1.517(5) . ?
C18 C23 1.388(5) . ?
C18 C19 1.401(5) . ?
C19 C20 1.375(5) . ?
C19 C24 1.518(5) . ?
C20 C21 1.400(5) . ?
C21 C22 1.380(6) . ?
C22 C23 1.382(5) . ?
C23 C27 1.515(5) . ?
C24 C26 1.498(5) . ?
C24 C25 1.522(5) . ?
C27 C29 1.506(6) . ?
C27 C28 1.512(7) . ?
C30 N31 1.343(4) . ?
N31 N32 1.267(4) . ?
N32 C33A 1.518(19) . ?
N32 C33 1.536(14) . ?
C33 C38 1.488(10) . ?
C33 C34 1.524(13) . ?
C34 O35 1.179(15) . ?
C34 O36 1.331(14) . ?
O36 C37 1.416(9) . ?
C38 C39 1.356(11) . ?
C38 C43 1.398(11) . ?
C39 C40 1.391(11) . ?
C40 C41 1.388(15) . ?
C41 C42 1.381(14) . ?
C42 C43 1.369(10) . ?
C33A C38A 1.496(15) . ?
C33A C34A 1.505(13) . ?
C34A O35A 1.194(13) . ?
C34A O36A 1.320(14) . ?
O36A C37A 1.452(14) . ?
C38A C39A 1.371(16) . ?
C38A C43A 1.398(17) . ?
C39A C40A 1.390(12) . ?
C40A C41A 1.393(15) . ?
C41A C42A 1.352(15) . ?
C42A C43A 1.366(12) . ?

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
C2 N1 C5 109.0(3) . . ?
C2 N1 C6 125.7(3) . . ?
C5 N1 C6 125.0(3) . . ?
N1 C2 N3 105.9(3) . . ?
N1 C2 C30 125.5(3) . . ?
N3 C2 C30 128.6(3) . . ?
C2 N3 C4 108.9(3) . . ?
C2 N3 C18 128.0(3) . . ?
C4 N3 C18 122.7(3) . . ?
C5 C4 N3 107.9(3) . . ?
C4 C5 N1 108.3(3) . . ?
C7 C6 C11 122.3(3) . . ?
C7 C6 N1 119.7(3) . . ?
C11 C6 N1 118.0(3) . . ?
C8 C7 C6 118.1(3) . . ?
C8 C7 C12 120.6(4) . . ?
C6 C7 C12 121.3(4) . . ?
C7 C8 C9 121.2(4) . . ?
C10 C9 C8 119.6(4) . . ?
C9 C10 C11 122.4(4) . . ?
C10 C11 C6 116.4(4) . . ?
C10 C11 C15 121.9(3) . . ?
C6 C11 C15 121.7(3) . . ?
C13 C12 C7 111.2(4) . . ?
C13 C12 C14 110.3(4) . . ?
C7 C12 C14 110.3(4) . . ?
C17 C15 C11 111.7(3) . . ?
C17 C15 C16 110.0(4) . . ?
C11 C15 C16 112.8(4) . . ?
C23 C18 C19 122.3(3) . . ?
C23 C18 N3 118.7(3) . . ?
C19 C18 N3 119.0(3) . . ?
C20 C19 C18 117.1(3) . . ?
C20 C19 C24 122.3(3) . . ?
C18 C19 C24 120.6(3) . . ?
C19 C20 C21 122.4(4) . . ?
C22 C21 C20 118.3(4) . . ?
C21 C22 C23 121.6(4) . . ?
C22 C23 C18 118.2(4) . . ?
C22 C23 C27 120.5(3) . . ?
C18 C23 C27 121.3(4) . . ?
C26 C24 C19 111.6(3) . . ?
C26 C24 C25 109.7(3) . . ?
C19 C24 C25 112.2(3) . . ?
C29 C27 C28 110.1(4) . . ?
C29 C27 C23 112.7(4) . . ?
C28 C27 C23 111.1(4) . . ?
N31 C30 C2 116.1(3) . . ?
N32 N31 C30 117.9(3) . . ?
N31 N32 C33A 110.0(6) . . ?
N31 N32 C33 105.8(5) . . ?
C38 C33 C34 112.7(9) . . ?
C38 C33 N32 104.7(7) . . ?
C34 C33 N32 111.2(10) . . ?
O35 C34 O36 123.2(11) . . ?
O35 C34 C33 126.4(11) . . ?
O36 C34 C33 110.3(11) . . ?
C34 O36 C37 115.6(8) . . ?
C39 C38 C43 118.8(7) . . ?
C39 C38 C33 122.4(8) . . ?
C43 C38 C33 118.8(9) . . ?
C38 C39 C40 120.9(10) . . ?
C41 C40 C39 119.2(10) . . ?
C42 C41 C40 120.7(9) . . ?
C43 C42 C41 118.5(9) . . ?
C42 C43 C38 121.8(8) . . ?
C38A C33A C34A 113.1(11) . . ?
C38A C33A N32 100.2(12) . . ?
C34A C33A N32 113.6(12) . . ?
O35A C34A O36A 121.1(10) . . ?
O35A C34A C33A 126.0(12) . . ?
O36A C34A C33A 112.8(11) . . ?
C34A O36A C37A 114.2(11) . . ?
C39A C38A C43A 118.0(12) . . ?
C39A C38A C33A 122.8(14) . . ?
C43A C38A C33A 119.1(13) . . ?
C38A C39A C40A 120.0(12) . . ?
C39A C40A C41A 120.2(11) . . ?
C42A C41A C40A 120.1(10) . . ?
C41A C42A C43A 119.4(11) . . ?
C42A C43A C38A 122.2(11) . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.087



####################################################################### 
# 
# 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_wl499_sq
_database_code_depnum_ccdc_archive 'CCDC 2209657'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2022-09-26 deposited with the CCDC.	2023-03-24 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            'C27 H25 N5 O'
_chemical_formula_weight         435.52

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   26.084(7)
_cell_length_b                   17.067(5)
_cell_length_c                   11.802(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5254(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    58567
_cell_measurement_theta_min      3.145
_cell_measurement_theta_max      27.444

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_F_000             1840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6539
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58567
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_av_R_equivalents  0.1133
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5976
_reflns_number_gt                3854
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²+1.9069P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0105(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5976
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
N2 N 0.63040(7) 0.20960(10) 0.44775(15) 0.0263(4) Uani 1 1 d . . . . .
N3 N 0.66425(7) 0.25668(10) 0.39917(14) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.70482(8) 0.27364(11) 0.46778(17) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.69502(8) 0.23455(12) 0.56671(19) 0.0224(4) Uani 1 1 d . . . . .
H5 H 0.7124(9) 0.2306(14) 0.634(2) 0.032(6) Uiso 1 1 d . . . . .
C6 C 0.62208(8) 0.14796(12) 0.63025(17) 0.0240(5) Uani 1 1 d . . . . .
N1 N 0.64979(6) 0.19685(10) 0.55006(14) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.60903(9) 0.02538(13) 0.71967(19) 0.0337(6) Uani 1 1 d . . . . .
H10 H 0.616445 -0.028895 0.726810 0.040 Uiso 1 1 calc R U . . .
C8 C 0.56240(8) 0.13801(15) 0.78152(19) 0.0323(5) Uani 1 1 d . . . . .
H8 H 0.537825 0.160996 0.830756 0.039 Uiso 1 1 calc R U . . .
C9 C 0.57350(9) 0.05882(15) 0.79261(19) 0.0344(6) Uani 1 1 d . . . . .
C7 C 0.58625(8) 0.18485(13) 0.70026(18) 0.0276(5) Uani 1 1 d . . . . .
C11 C 0.63430(8) 0.06870(13) 0.63602(18) 0.0291(5) Uani 1 1 d . . . . .
C12 C 0.57484(9) 0.27118(14) 0.6881(2) 0.0385(6) Uani 1 1 d . . . . .
H12A H 0.562398 0.281782 0.611250 0.058 Uiso 1 1 calc R U . . .
H12B H 0.606170 0.301400 0.701932 0.058 Uiso 1 1 calc R U . . .
H12C H 0.548554 0.286403 0.743183 0.058 Uiso 1 1 calc R U . . .
C13 C 0.54668(11) 0.01023(18) 0.8820(2) 0.0498(7) Uani 1 1 d . . . . .
H13A H 0.509513 0.013211 0.870644 0.075 Uiso 1 1 calc R U . . .
H13B H 0.555317 0.030442 0.957350 0.075 Uiso 1 1 calc R U . . .
H13C H 0.557842 -0.044439 0.875925 0.075 Uiso 1 1 calc R U . . .
C14 C 0.67185(10) 0.03159(14) 0.5556(2) 0.0378(6) Uani 1 1 d . . . . .
H14A H 0.657361 0.031337 0.478953 0.057 Uiso 1 1 calc R U . . .
H14B H 0.678765 -0.022362 0.579547 0.057 Uiso 1 1 calc R U . . .
H14C H 0.703875 0.061601 0.555787 0.057 Uiso 1 1 calc R U . . .
C15 C 0.65504(9) 0.28201(14) 0.28136(18) 0.0331(5) Uani 1 1 d . . . . .
H15A H 0.675473 0.249711 0.229652 0.050 Uiso 1 1 calc R U . . .
H15B H 0.664940 0.337097 0.272963 0.050 Uiso 1 1 calc R U . . .
H15C H 0.618581 0.276046 0.263219 0.050 Uiso 1 1 calc R U . . .
C16 C 0.74865(8) 0.32440(12) 0.43119(17) 0.0225(4) Uani 1 1 d . . . . .
N17 N 0.77144(7) 0.28727(10) 0.32746(15) 0.0257(4) Uani 1 1 d . . . . .
N18 N 0.81736(7) 0.26544(10) 0.35256(15) 0.0256(4) Uani 1 1 d . . . . .
C19 C 0.83236(8) 0.28389(12) 0.46123(18) 0.0249(5) Uani 1 1 d . . . . .
C20 C 0.79205(8) 0.32038(11) 0.52010(17) 0.0237(5) Uani 1 1 d . . . . .
O21 O 0.78767(6) 0.34502(8) 0.61930(12) 0.0281(4) Uani 1 1 d . . . . .
C22 C 0.73282(8) 0.40953(12) 0.41181(17) 0.0249(5) Uani 1 1 d . . . . .
C23 C 0.70070(9) 0.44700(13) 0.4896(2) 0.0345(6) Uani 1 1 d . . . . .
H23 H 0.686986 0.418497 0.551698 0.041 Uiso 1 1 calc R U . . .
C24 C 0.68880(11) 0.52554(14) 0.4763(3) 0.0466(7) Uani 1 1 d . . . . .
H24 H 0.667038 0.550946 0.529357 0.056 Uiso 1 1 calc R U . . .
C25 C 0.70869(11) 0.56695(15) 0.3856(2) 0.0473(7) Uani 1 1 d . . . . .
H25 H 0.700302 0.620737 0.376317 0.057 Uiso 1 1 calc R U . . .
C26 C 0.74054(10) 0.53082(14) 0.3086(2) 0.0417(6) Uani 1 1 d . . . . .
H26 H 0.754182 0.559598 0.246615 0.050 Uiso 1 1 calc R U . . .
C27 C 0.75262(9) 0.45210(13) 0.32194(19) 0.0329(5) Uani 1 1 d . . . . .
H27 H 0.774675 0.427207 0.268949 0.039 Uiso 1 1 calc R U . . .
C28 C 0.88438(8) 0.26658(13) 0.50372(18) 0.0269(5) Uani 1 1 d . . . . .
C29 C 0.90966(9) 0.32049(15) 0.5732(2) 0.0358(6) Uani 1 1 d . . . . .
H29 H 0.892763 0.367725 0.593679 0.043 Uiso 1 1 calc R U . . .
C30 C 0.95874(11) 0.30657(18) 0.6127(2) 0.0496(7) Uani 1 1 d . . . . .
H30 H 0.975201 0.344075 0.659757 0.060 Uiso 1 1 calc R U . . .
C31 C 0.98384(10) 0.2381(2) 0.5838(3) 0.0562(8) Uani 1 1 d . . . . .
H31 H 1.017591 0.228559 0.610719 0.067 Uiso 1 1 calc R U . . .
C32 C 0.95959(10) 0.18339(18) 0.5153(3) 0.0544(8) Uani 1 1 d . . . . .
H32 H 0.976731 0.136246 0.495400 0.065 Uiso 1 1 calc R U . . .
C33 C 0.91007(9) 0.19755(14) 0.4757(2) 0.0374(6) Uani 1 1 d . . . . .
H33 H 0.893648 0.159756 0.429006 0.045 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
N2 N3 1.324(2) . ?
N2 N1 1.327(2) . ?
N3 C4 1.363(3) . ?
N3 C15 1.476(3) . ?
C4 C5 1.369(3) . ?
C4 C16 1.498(3) . ?
C5 N1 1.358(3) . ?
C5 H5 0.92(2) . ?
C6 C11 1.391(3) . ?
C6 C7 1.397(3) . ?
C6 N1 1.454(3) . ?
C10 C9 1.388(3) . ?
C10 C11 1.399(3) . ?
C10 H10 0.9500 . ?
C8 C9 1.388(3) . ?
C8 C7 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C13 1.513(3) . ?
C7 C12 1.510(3) . ?
C11 C14 1.504(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N17 1.501(3) . ?
C16 C22 1.528(3) . ?
C16 C20 1.545(3) . ?
N17 N18 1.289(2) . ?
N18 C19 1.377(3) . ?
C19 C20 1.406(3) . ?
C19 C28 1.476(3) . ?
C20 O21 1.249(2) . ?
C22 C27 1.386(3) . ?
C22 C23 1.397(3) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.377(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.389(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.395(3) . ?
C28 C29 1.398(3) . ?
C29 C30 1.383(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.388(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.395(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N2 N1 103.84(16) . . ?
N2 N3 C4 112.90(16) . . ?
N2 N3 C15 118.49(17) . . ?
C4 N3 C15 128.58(18) . . ?
N3 C4 C5 104.97(18) . . ?
N3 C4 C16 122.95(17) . . ?
C5 C4 C16 132.08(19) . . ?
N1 C5 C4 105.64(19) . . ?
N1 C5 H5 121.2(15) . . ?
C4 C5 H5 133.1(15) . . ?
C11 C6 C7 124.2(2) . . ?
C11 C6 N1 118.41(18) . . ?
C7 C6 N1 117.30(19) . . ?
N2 N1 C5 112.65(17) . . ?
N2 N1 C6 119.78(16) . . ?
C5 N1 C6 127.56(18) . . ?
C9 C10 C11 122.4(2) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C9 C8 C7 122.0(2) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 C13 121.0(2) . . ?
C8 C9 C13 120.2(2) . . ?
C8 C7 C6 116.5(2) . . ?
C8 C7 C12 122.5(2) . . ?
C6 C7 C12 121.0(2) . . ?
C6 C11 C10 116.1(2) . . ?
C6 C11 C14 121.86(19) . . ?
C10 C11 C14 122.0(2) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C16 N17 107.05(16) . . ?
C4 C16 C22 112.76(17) . . ?
N17 C16 C22 112.73(16) . . ?
C4 C16 C20 109.74(16) . . ?
N17 C16 C20 104.17(16) . . ?
C22 C16 C20 109.99(16) . . ?
N18 N17 C16 107.61(16) . . ?
N17 N18 C19 114.33(17) . . ?
N18 C19 C20 110.43(19) . . ?
N18 C19 C28 122.12(18) . . ?
C20 C19 C28 127.45(19) . . ?
O21 C20 C19 132.9(2) . . ?
O21 C20 C16 123.66(19) . . ?
C19 C20 C16 103.42(17) . . ?
C27 C22 C23 119.1(2) . . ?
C27 C22 C16 120.83(19) . . ?
C23 C22 C16 119.93(18) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.7(2) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C22 C27 C26 120.6(2) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C33 C28 C29 117.9(2) . . ?
C33 C28 C19 122.0(2) . . ?
C29 C28 C19 120.1(2) . . ?
C30 C29 C28 121.4(2) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C31 C30 C29 120.0(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 119.8(2) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 120.1(3) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 C28 120.8(2) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 N3 C4 0.5(2) . . . . ?
N1 N2 N3 C15 178.89(17) . . . . ?
N2 N3 C4 C5 -0.6(2) . . . . ?
C15 N3 C4 C5 -178.8(2) . . . . ?
N2 N3 C4 C16 178.75(18) . . . . ?
C15 N3 C4 C16 0.5(3) . . . . ?
N3 C4 C5 N1 0.4(2) . . . . ?
C16 C4 C5 N1 -178.8(2) . . . . ?
N3 N2 N1 C5 -0.2(2) . . . . ?
N3 N2 N1 C6 178.77(17) . . . . ?
C4 C5 N1 N2 -0.1(2) . . . . ?
C4 C5 N1 C6 -179.01(19) . . . . ?
C11 C6 N1 N2 94.1(2) . . . . ?
C7 C6 N1 N2 -88.6(2) . . . . ?
C11 C6 N1 C5 -87.1(3) . . . . ?
C7 C6 N1 C5 90.2(3) . . . . ?
C11 C10 C9 C8 0.5(3) . . . . ?
C11 C10 C9 C13 179.8(2) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 C13 -180.0(2) . . . . ?
C9 C8 C7 C6 0.0(3) . . . . ?
C9 C8 C7 C12 -179.4(2) . . . . ?
C11 C6 C7 C8 1.0(3) . . . . ?
N1 C6 C7 C8 -176.04(18) . . . . ?
C11 C6 C7 C12 -179.6(2) . . . . ?
N1 C6 C7 C12 3.4(3) . . . . ?
C7 C6 C11 C10 -1.2(3) . . . . ?
N1 C6 C11 C10 175.84(19) . . . . ?
C7 C6 C11 C14 177.8(2) . . . . ?
N1 C6 C11 C14 -5.2(3) . . . . ?
C9 C10 C11 C6 0.4(3) . . . . ?
C9 C10 C11 C14 -178.6(2) . . . . ?
N3 C4 C16 N17 -57.9(2) . . . . ?
C5 C4 C16 N17 121.2(2) . . . . ?
N3 C4 C16 C22 66.6(2) . . . . ?
C5 C4 C16 C22 -114.3(2) . . . . ?
N3 C4 C16 C20 -170.40(17) . . . . ?
C5 C4 C16 C20 8.7(3) . . . . ?
C4 C16 N17 N18 -115.14(18) . . . . ?
C22 C16 N17 N18 120.30(18) . . . . ?
C20 C16 N17 N18 1.1(2) . . . . ?
C16 N17 N18 C19 -2.0(2) . . . . ?
N17 N18 C19 C20 2.1(2) . . . . ?
N17 N18 C19 C28 -177.37(18) . . . . ?
N18 C19 C20 O21 178.0(2) . . . . ?
C28 C19 C20 O21 -2.5(4) . . . . ?
N18 C19 C20 C16 -1.2(2) . . . . ?
C28 C19 C20 C16 178.25(19) . . . . ?
C4 C16 C20 O21 -64.9(2) . . . . ?
N17 C16 C20 O21 -179.19(18) . . . . ?
C22 C16 C20 O21 59.7(2) . . . . ?
C4 C16 C20 C19 114.43(18) . . . . ?
N17 C16 C20 C19 0.11(19) . . . . ?
C22 C16 C20 C19 -120.96(18) . . . . ?
C4 C16 C22 C27 -140.4(2) . . . . ?
N17 C16 C22 C27 -19.0(3) . . . . ?
C20 C16 C22 C27 96.7(2) . . . . ?
C4 C16 C22 C23 44.0(3) . . . . ?
N17 C16 C22 C23 165.32(19) . . . . ?
C20 C16 C22 C23 -78.9(2) . . . . ?
C27 C22 C23 C24 0.2(3) . . . . ?
C16 C22 C23 C24 176.0(2) . . . . ?
C22 C23 C24 C25 0.2(4) . . . . ?
C23 C24 C25 C26 -0.4(4) . . . . ?
C24 C25 C26 C27 0.2(4) . . . . ?
C23 C22 C27 C26 -0.4(3) . . . . ?
C16 C22 C27 C26 -176.1(2) . . . . ?
C25 C26 C27 C22 0.2(4) . . . . ?
N18 C19 C28 C33 -38.9(3) . . . . ?
C20 C19 C28 C33 141.7(2) . . . . ?
N18 C19 C28 C29 140.3(2) . . . . ?
C20 C19 C28 C29 -39.1(3) . . . . ?
C33 C28 C29 C30 0.4(3) . . . . ?
C19 C28 C29 C30 -178.9(2) . . . . ?
C28 C29 C30 C31 -0.1(4) . . . . ?
C29 C30 C31 C32 -0.2(4) . . . . ?
C30 C31 C32 C33 0.1(4) . . . . ?
C31 C32 C33 C28 0.2(4) . . . . ?
C29 C28 C33 C32 -0.5(4) . . . . ?
C19 C28 C33 C32 178.8(2) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.065




####################################################################### 
# 
# 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_wl601_sq
_database_code_depnum_ccdc_archive 'CCDC 2243055'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 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            'C49 H54 N4 O2'
_chemical_formula_weight         730.96

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.713(5)
_cell_length_b                   27.880(12)
_cell_length_c                   15.682(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.665(13)
_cell_angle_gamma                90
_cell_volume                     5495(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    157823
_cell_measurement_theta_min      1.461
_cell_measurement_theta_max      27.679

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.884
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.054
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            157823
_diffrn_reflns_av_unetI/netI     0.1210
_diffrn_reflns_av_R_equivalents  0.1629
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.461
_diffrn_reflns_theta_max         27.679
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12762
_reflns_number_gt                6773
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0802P)²+0.3351P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0088(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         12762
_refine_ls_number_parameters     506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1967
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
N1 N 0.73010(13) 0.67973(6) 0.50651(12) 0.0325(4) Uani 1 1 d . . . . .
C2 C 0.70840(16) 0.65640(7) 0.57649(14) 0.0329(5) Uani 1 1 d . . . . .
N3 N 0.63461(13) 0.62313(6) 0.54995(11) 0.0308(4) Uani 1 1 d . . . . .
C4 C 0.60749(15) 0.62547(7) 0.46122(14) 0.0294(5) Uani 1 1 d . . . . .
C5 C 0.66736(16) 0.66080(7) 0.43329(14) 0.0319(5) Uani 1 1 d . . . . .
C6 C 0.81911(16) 0.71229(8) 0.50260(14) 0.0364(5) Uani 1 1 d . . . . .
C7 C 0.92139(17) 0.69242(8) 0.51629(14) 0.0373(5) Uani 1 1 d . . . . .
C8 C 1.00474(18) 0.72250(9) 0.50367(15) 0.0436(6) Uani 1 1 d . . . . .
H8 H 1.075262 0.710243 0.511519 0.052 Uiso 1 1 calc R U . . .
C9 C 0.98738(19) 0.76934(9) 0.48019(16) 0.0487(6) Uani 1 1 d . . . . .
H9 H 1.045541 0.789095 0.471046 0.058 Uiso 1 1 calc R U . . .
C10 C 0.88618(19) 0.78808(9) 0.46973(16) 0.0481(6) Uani 1 1 d . . . . .
H10 H 0.875777 0.821040 0.455533 0.058 Uiso 1 1 calc R U . . .
C11 C 0.79847(18) 0.75965(8) 0.47954(16) 0.0427(6) Uani 1 1 d . . . . .
C12 C 0.94690(18) 0.64102(8) 0.54278(15) 0.0442(6) Uani 1 1 d . . . . .
H12 H 0.879127 0.624766 0.551243 0.053 Uiso 1 1 calc R U . . .
C13 C 0.9949(2) 0.61363(10) 0.47423(19) 0.0693(8) Uani 1 1 d . . . . .
H13A H 1.014881 0.581322 0.495398 0.104 Uiso 1 1 calc R U . . .
H13B H 1.058290 0.630554 0.461420 0.104 Uiso 1 1 calc R U . . .
H13C H 0.942631 0.611349 0.421681 0.104 Uiso 1 1 calc R U . . .
C14 C 1.0224(2) 0.63977(11) 0.62840(18) 0.0704(8) Uani 1 1 d . . . . .
H14A H 1.031496 0.606542 0.648561 0.106 Uiso 1 1 calc R U . . .
H14B H 0.992405 0.658932 0.671304 0.106 Uiso 1 1 calc R U . . .
H14C H 1.091533 0.653018 0.620232 0.106 Uiso 1 1 calc R U . . .
C15 C 0.68912(19) 0.78276(9) 0.46557(19) 0.0564(7) Uani 1 1 d . . . . .
H15 H 0.635112 0.757368 0.471428 0.068 Uiso 1 1 calc R U . . .
C16 C 0.6652(2) 0.80368(10) 0.3747(2) 0.0781(10) Uani 1 1 d . . . . .
H16A H 0.591639 0.815364 0.364306 0.117 Uiso 1 1 calc R U . . .
H16B H 0.674561 0.778776 0.332408 0.117 Uiso 1 1 calc R U . . .
H16C H 0.713909 0.830337 0.369103 0.117 Uiso 1 1 calc R U . . .
C17 C 0.6803(2) 0.82153(9) 0.5333(3) 0.0807(10) Uani 1 1 d . . . . .
H17A H 0.609488 0.836166 0.522359 0.121 Uiso 1 1 calc R U . . .
H17B H 0.734509 0.846183 0.530064 0.121 Uiso 1 1 calc R U . . .
H17C H 0.691330 0.807039 0.590922 0.121 Uiso 1 1 calc R U . . .
C18 C 0.75742(17) 0.66672(8) 0.66541(15) 0.0389(6) Uani 1 1 d . . . . .
C19 C 0.77589(17) 0.71429(9) 0.68980(16) 0.0452(6) Uani 1 1 d . . . . .
H19 H 0.754841 0.739487 0.650097 0.054 Uiso 1 1 calc R U . . .
C20 C 0.8252(2) 0.72451(11) 0.7725(2) 0.0621(8) Uani 1 1 d . . . . .
H20 H 0.838686 0.756960 0.789141 0.074 Uiso 1 1 calc R U . . .
C21 C 0.8550(2) 0.68865(13) 0.8307(2) 0.0744(10) Uani 1 1 d . . . . .
H21 H 0.889463 0.696142 0.887161 0.089 Uiso 1 1 calc R U . . .
C22 C 0.8349(2) 0.64215(12) 0.80716(18) 0.0726(9) Uani 1 1 d . . . . .
H22 H 0.854503 0.617297 0.847901 0.087 Uiso 1 1 calc R U . . .
C23 C 0.7867(2) 0.63063(10) 0.72523(16) 0.0529(7) Uani 1 1 d . . . . .
H23 H 0.773445 0.598019 0.709634 0.064 Uiso 1 1 calc R U . . .
C24 C 0.59873(17) 0.58601(7) 0.60480(14) 0.0326(5) Uani 1 1 d . . . . .
C25 C 0.64494(17) 0.54056(7) 0.60155(14) 0.0350(5) Uani 1 1 d . . . . .
C26 C 0.61549(18) 0.50632(8) 0.65815(15) 0.0407(6) Uani 1 1 d . . . . .
H26 H 0.645177 0.475033 0.658508 0.049 Uiso 1 1 calc R U . . .
C27 C 0.5449(2) 0.51665(8) 0.71317(16) 0.0460(6) Uani 1 1 d . . . . .
H27 H 0.527410 0.492846 0.752046 0.055 Uiso 1 1 calc R U . . .
C28 C 0.49901(19) 0.56139(8) 0.71257(15) 0.0437(6) Uani 1 1 d . . . . .
H28 H 0.448628 0.567727 0.750148 0.052 Uiso 1 1 calc R U . . .
C29 C 0.52464(18) 0.59731(7) 0.65848(14) 0.0373(5) Uani 1 1 d . . . . .
C30 C 0.72546(17) 0.52738(8) 0.54263(16) 0.0414(6) Uani 1 1 d . . . . .
H30 H 0.732918 0.555369 0.504115 0.050 Uiso 1 1 calc R U . . .
C31 C 0.6880(2) 0.48437(8) 0.48603(16) 0.0511(7) Uani 1 1 d . . . . .
H31A H 0.617708 0.491185 0.453212 0.077 Uiso 1 1 calc R U . . .
H31B H 0.683446 0.456110 0.522477 0.077 Uiso 1 1 calc R U . . .
H31C H 0.738658 0.478160 0.446040 0.077 Uiso 1 1 calc R U . . .
C32 C 0.83511(19) 0.51664(9) 0.59458(18) 0.0553(7) Uani 1 1 d . . . . .
H32A H 0.861965 0.545308 0.626915 0.083 Uiso 1 1 calc R U . . .
H32B H 0.884523 0.507450 0.555125 0.083 Uiso 1 1 calc R U . . .
H32C H 0.828860 0.490294 0.634889 0.083 Uiso 1 1 calc R U . . .
C33 C 0.47187(18) 0.64592(8) 0.66061(15) 0.0421(6) Uani 1 1 d . . . . .
H33 H 0.496738 0.666825 0.615822 0.050 Uiso 1 1 calc R U . . .
C34 C 0.3510(2) 0.64110(9) 0.64015(17) 0.0526(7) Uani 1 1 d . . . . .
H34A H 0.331816 0.625871 0.583624 0.079 Uiso 1 1 calc R U . . .
H34B H 0.318378 0.672982 0.639280 0.079 Uiso 1 1 calc R U . . .
H34C H 0.325244 0.621364 0.684417 0.079 Uiso 1 1 calc R U . . .
C35 C 0.5034(2) 0.66947(9) 0.74898(17) 0.0572(7) Uani 1 1 d . . . . .
H35A H 0.580348 0.675251 0.758901 0.086 Uiso 1 1 calc R U . . .
H35B H 0.484437 0.648206 0.794022 0.086 Uiso 1 1 calc R U . . .
H35C H 0.465723 0.700043 0.750555 0.086 Uiso 1 1 calc R U . . .
C36 C 0.52827(16) 0.59322(7) 0.41020(14) 0.0337(5) Uani 1 1 d . . . . .
H36A H 0.554769 0.584901 0.355852 0.040 Uiso 1 1 calc R U . . .
H36B H 0.524529 0.563110 0.443067 0.040 Uiso 1 1 calc R U . . .
N37 N 0.42004(13) 0.61242(6) 0.38840(12) 0.0362(4) Uani 1 1 d . . . . .
N38 N 0.41061(13) 0.65207(6) 0.42892(11) 0.0330(4) Uani 1 1 d . . . . .
C39 C 0.31872(16) 0.67713(7) 0.41776(14) 0.0339(5) Uani 1 1 d . . . . .
C40 C 0.21985(17) 0.66535(7) 0.36029(15) 0.0370(5) Uani 1 1 d . . . . .
C41 C 0.19980(19) 0.62000(9) 0.32473(18) 0.0579(8) Uani 1 1 d . . . . .
H41 H 0.251186 0.595402 0.338844 0.070 Uiso 1 1 calc R U . . .
C42 C 0.1073(2) 0.60962(9) 0.2694(2) 0.0682(9) Uani 1 1 d . . . . .
H42 H 0.096492 0.578211 0.246257 0.082 Uiso 1 1 calc R U . . .
C43 C 0.0312(2) 0.64393(9) 0.24759(18) 0.0563(7) Uani 1 1 d . . . . .
H43 H -0.032712 0.636628 0.210219 0.068 Uiso 1 1 calc R U . . .
C44 C 0.04945(18) 0.68902(8) 0.28086(16) 0.0461(6) Uani 1 1 d . . . . .
H44 H -0.002305 0.713360 0.265797 0.055 Uiso 1 1 calc R U . . .
C45 C 0.14130(17) 0.69977(8) 0.33572(15) 0.0396(6) Uani 1 1 d . . . . .
H45 H 0.151618 0.731493 0.357500 0.048 Uiso 1 1 calc R U . . .
C46 C 0.32507(17) 0.71885(8) 0.47173(14) 0.0352(5) Uani 1 1 d . . . . .
O47 O 0.25165(12) 0.74326(5) 0.48967(11) 0.0467(4) Uani 1 1 d . . . . .
O48 O 0.42735(11) 0.73134(5) 0.50544(10) 0.0396(4) Uani 1 1 d . . . . .
C49 C 0.4356(2) 0.76693(9) 0.57113(16) 0.0497(6) Uani 1 1 d . . . . .
H49A H 0.510802 0.772516 0.593628 0.075 Uiso 1 1 calc R U . . .
H49B H 0.398522 0.755943 0.617971 0.075 Uiso 1 1 calc R U . . .
H49C H 0.403285 0.796840 0.547049 0.075 Uiso 1 1 calc R U . . .
C50 C 0.66793(17) 0.67860(8) 0.34569(15) 0.0377(5) Uani 1 1 d . . . . .
C51 C 0.76046(18) 0.68085(9) 0.30924(16) 0.0475(6) Uani 1 1 d . . . . .
H51 H 0.826070 0.670924 0.341619 0.057 Uiso 1 1 calc R U . . .
C52 C 0.75775(19) 0.69732(10) 0.22674(17) 0.0577(7) Uani 1 1 d . . . . .
H52 H 0.821699 0.698317 0.202300 0.069 Uiso 1 1 calc R U . . .
C53 C 0.6643(2) 0.71247(10) 0.17853(18) 0.0616(8) Uani 1 1 d . . . . .
H53 H 0.663588 0.724461 0.121739 0.074 Uiso 1 1 calc R U . . .
C54 C 0.5710(2) 0.70990(10) 0.21440(18) 0.0615(8) Uani 1 1 d . . . . .
H54 H 0.505580 0.719808 0.181740 0.074 Uiso 1 1 calc R U . . .
C55 C 0.57314(18) 0.69309(9) 0.29687(16) 0.0495(7) Uani 1 1 d . . . . .
H55 H 0.508911 0.691364 0.320824 0.059 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
N1 C2 1.340(3) . ?
N1 C5 1.399(3) . ?
N1 C6 1.459(3) . ?
C2 N3 1.340(3) . ?
C2 C18 1.468(3) . ?
N3 C4 1.384(3) . ?
N3 C24 1.462(3) . ?
C4 C5 1.357(3) . ?
C4 C36 1.490(3) . ?
C5 C50 1.462(3) . ?
C6 C11 1.384(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.514(3) . ?
C8 C9 1.366(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(3) . ?
C10 H10 0.9500 . ?
C11 C15 1.518(3) . ?
C12 C13 1.520(3) . ?
C12 C14 1.528(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.527(4) . ?
C15 C17 1.532(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.388(3) . ?
C18 C19 1.391(3) . ?
C19 C20 1.382(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.369(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.361(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.376(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.391(3) . ?
C24 C25 1.401(3) . ?
C25 C26 1.393(3) . ?
C25 C30 1.524(3) . ?
C26 C27 1.366(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.376(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(3) . ?
C28 H28 0.9500 . ?
C29 C33 1.515(3) . ?
C30 C31 1.525(3) . ?
C30 C32 1.534(3) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.528(3) . ?
C33 C35 1.531(3) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N37 1.468(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
N37 N38 1.290(2) . ?
N38 C39 1.350(3) . ?
C39 C46 1.433(3) . ?
C39 C40 1.469(3) . ?
C40 C41 1.390(3) . ?
C40 C45 1.397(3) . ?
C41 C42 1.383(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.366(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.367(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.375(3) . ?
C44 H44 0.9500 . ?
C45 H45 0.9500 . ?
C46 O47 1.222(2) . ?
C46 O48 1.373(3) . ?
O48 C49 1.423(3) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 C51 1.385(3) . ?
C50 C55 1.387(3) . ?
C51 C52 1.368(3) . ?
C51 H51 0.9500 . ?
C52 C53 1.375(3) . ?
C52 H52 0.9500 . ?
C53 C54 1.389(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.372(3) . ?
C54 H54 0.9500 . ?
C55 H55 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 109.08(17) . . ?
C2 N1 C6 126.38(18) . . ?
C5 N1 C6 123.37(18) . . ?
N1 C2 N3 107.61(18) . . ?
N1 C2 C18 124.95(19) . . ?
N3 C2 C18 127.4(2) . . ?
C2 N3 C4 109.66(17) . . ?
C2 N3 C24 124.97(18) . . ?
C4 N3 C24 124.92(17) . . ?
C5 C4 N3 106.97(18) . . ?
C5 C4 C36 129.1(2) . . ?
N3 C4 C36 123.89(18) . . ?
C4 C5 N1 106.68(18) . . ?
C4 C5 C50 129.21(19) . . ?
N1 C5 C50 124.08(18) . . ?
C11 C6 C7 123.6(2) . . ?
C11 C6 N1 119.14(19) . . ?
C7 C6 N1 117.12(19) . . ?
C8 C7 C6 116.8(2) . . ?
C8 C7 C12 118.3(2) . . ?
C6 C7 C12 124.92(19) . . ?
C9 C8 C7 121.3(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C6 C11 C10 116.6(2) . . ?
C6 C11 C15 125.2(2) . . ?
C10 C11 C15 118.2(2) . . ?
C7 C12 C13 112.0(2) . . ?
C7 C12 C14 110.1(2) . . ?
C13 C12 C14 110.1(2) . . ?
C7 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
C14 C12 H12 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 110.3(2) . . ?
C11 C15 C17 111.1(2) . . ?
C16 C15 C17 110.6(2) . . ?
C11 C15 H15 108.2 . . ?
C16 C15 H15 108.2 . . ?
C17 C15 H15 108.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 119.2(2) . . ?
C23 C18 C2 122.2(2) . . ?
C19 C18 C2 118.6(2) . . ?
C20 C19 C18 119.3(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 119.9(3) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C29 C24 C25 123.57(19) . . ?
C29 C24 N3 119.71(18) . . ?
C25 C24 N3 116.69(19) . . ?
C26 C25 C24 116.2(2) . . ?
C26 C25 C30 119.41(19) . . ?
C24 C25 C30 124.33(19) . . ?
C27 C26 C25 121.6(2) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C28 120.3(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 121.4(2) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C28 C29 C24 116.8(2) . . ?
C28 C29 C33 119.2(2) . . ?
C24 C29 C33 123.97(19) . . ?
C25 C30 C31 111.28(19) . . ?
C25 C30 C32 111.4(2) . . ?
C31 C30 C32 109.56(19) . . ?
C25 C30 H30 108.2 . . ?
C31 C30 H30 108.2 . . ?
C32 C30 H30 108.2 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C33 C34 110.59(19) . . ?
C29 C33 C35 110.3(2) . . ?
C34 C33 C35 110.2(2) . . ?
C29 C33 H33 108.5 . . ?
C34 C33 H33 108.5 . . ?
C35 C33 H33 108.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N37 C36 C4 116.04(17) . . ?
N37 C36 H36A 108.3 . . ?
C4 C36 H36A 108.3 . . ?
N37 C36 H36B 108.3 . . ?
C4 C36 H36B 108.3 . . ?
H36A C36 H36B 107.4 . . ?
N38 N37 C36 110.57(16) . . ?
N37 N38 C39 121.52(18) . . ?
N38 C39 C46 111.89(19) . . ?
N38 C39 C40 127.41(19) . . ?
C46 C39 C40 120.69(18) . . ?
C41 C40 C45 115.7(2) . . ?
C41 C40 C39 122.53(19) . . ?
C45 C40 C39 121.7(2) . . ?
C42 C41 C40 122.0(2) . . ?
C42 C41 H41 119.0 . . ?
C40 C41 H41 119.0 . . ?
C43 C42 C41 120.9(2) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C42 C43 C44 118.4(2) . . ?
C42 C43 H43 120.8 . . ?
C44 C43 H43 120.8 . . ?
C43 C44 C45 121.2(2) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 H44 119.4 . . ?
C44 C45 C40 121.8(2) . . ?
C44 C45 H45 119.1 . . ?
C40 C45 H45 119.1 . . ?
O47 C46 O48 118.8(2) . . ?
O47 C46 C39 127.7(2) . . ?
O48 C46 C39 113.52(18) . . ?
C46 O48 C49 114.73(17) . . ?
O48 C49 H49A 109.5 . . ?
O48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
O48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C51 C50 C55 118.7(2) . . ?
C51 C50 C5 121.9(2) . . ?
C55 C50 C5 119.4(2) . . ?
C52 C51 C50 120.2(2) . . ?
C52 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C51 C52 C53 121.3(2) . . ?
C51 C52 H52 119.3 . . ?
C53 C52 H52 119.3 . . ?
C52 C53 C54 118.8(2) . . ?
C52 C53 H53 120.6 . . ?
C54 C53 H53 120.6 . . ?
C55 C54 C53 120.2(2) . . ?
C55 C54 H54 119.9 . . ?
C53 C54 H54 119.9 . . ?
C54 C55 C50 120.8(2) . . ?
C54 C55 H55 119.6 . . ?
C50 C55 H55 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 0.4(2) . . . . ?
C6 N1 C2 N3 -167.47(18) . . . . ?
C5 N1 C2 C18 -179.01(19) . . . . ?
C6 N1 C2 C18 13.1(3) . . . . ?
N1 C2 N3 C4 -0.7(2) . . . . ?
C18 C2 N3 C4 178.77(19) . . . . ?
N1 C2 N3 C24 171.92(17) . . . . ?
C18 C2 N3 C24 -8.7(3) . . . . ?
C2 N3 C4 C5 0.6(2) . . . . ?
C24 N3 C4 C5 -171.95(18) . . . . ?
C2 N3 C4 C36 179.42(18) . . . . ?
C24 N3 C4 C36 6.8(3) . . . . ?
N3 C4 C5 N1 -0.3(2) . . . . ?
C36 C4 C5 N1 -179.05(19) . . . . ?
N3 C4 C5 C50 -178.4(2) . . . . ?
C36 C4 C5 C50 2.9(4) . . . . ?
C2 N1 C5 C4 0.0(2) . . . . ?
C6 N1 C5 C4 168.30(18) . . . . ?
C2 N1 C5 C50 178.17(19) . . . . ?
C6 N1 C5 C50 -13.5(3) . . . . ?
C2 N1 C6 C11 -118.4(2) . . . . ?
C5 N1 C6 C11 75.3(3) . . . . ?
C2 N1 C6 C7 66.4(3) . . . . ?
C5 N1 C6 C7 -99.9(2) . . . . ?
C11 C6 C7 C8 -1.5(3) . . . . ?
N1 C6 C7 C8 173.51(19) . . . . ?
C11 C6 C7 C12 179.1(2) . . . . ?
N1 C6 C7 C12 -5.9(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C12 C7 C8 C9 -179.6(2) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C8 C9 C10 C11 -2.4(4) . . . . ?
C7 C6 C11 C10 0.2(3) . . . . ?
N1 C6 C11 C10 -174.7(2) . . . . ?
C7 C6 C11 C15 -178.9(2) . . . . ?
N1 C6 C11 C15 6.2(4) . . . . ?
C9 C10 C11 C6 1.8(4) . . . . ?
C9 C10 C11 C15 -179.1(2) . . . . ?
C8 C7 C12 C13 -62.9(3) . . . . ?
C6 C7 C12 C13 116.5(3) . . . . ?
C8 C7 C12 C14 59.9(3) . . . . ?
C6 C7 C12 C14 -120.7(3) . . . . ?
C6 C11 C15 C16 -122.5(3) . . . . ?
C10 C11 C15 C16 58.4(3) . . . . ?
C6 C11 C15 C17 114.4(3) . . . . ?
C10 C11 C15 C17 -64.7(3) . . . . ?
N1 C2 C18 C23 -140.2(2) . . . . ?
N3 C2 C18 C23 40.4(3) . . . . ?
N1 C2 C18 C19 39.1(3) . . . . ?
N3 C2 C18 C19 -140.3(2) . . . . ?
C23 C18 C19 C20 1.5(3) . . . . ?
C2 C18 C19 C20 -177.9(2) . . . . ?
C18 C19 C20 C21 -0.7(4) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C23 1.1(5) . . . . ?
C21 C22 C23 C18 -0.3(4) . . . . ?
C19 C18 C23 C22 -1.0(4) . . . . ?
C2 C18 C23 C22 178.3(2) . . . . ?
C2 N3 C24 C29 80.1(3) . . . . ?
C4 N3 C24 C29 -108.5(2) . . . . ?
C2 N3 C24 C25 -98.0(2) . . . . ?
C4 N3 C24 C25 73.4(3) . . . . ?
C29 C24 C25 C26 -2.1(3) . . . . ?
N3 C24 C25 C26 175.92(18) . . . . ?
C29 C24 C25 C30 179.4(2) . . . . ?
N3 C24 C25 C30 -2.5(3) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C30 C25 C26 C27 178.9(2) . . . . ?
C25 C26 C27 C28 1.4(4) . . . . ?
C26 C27 C28 C29 -1.7(4) . . . . ?
C27 C28 C29 C24 0.1(3) . . . . ?
C27 C28 C29 C33 -179.9(2) . . . . ?
C25 C24 C29 C28 1.9(3) . . . . ?
N3 C24 C29 C28 -176.10(19) . . . . ?
C25 C24 C29 C33 -178.2(2) . . . . ?
N3 C24 C29 C33 3.9(3) . . . . ?
C26 C25 C30 C31 57.5(3) . . . . ?
C24 C25 C30 C31 -124.1(2) . . . . ?
C26 C25 C30 C32 -65.1(3) . . . . ?
C24 C25 C30 C32 113.3(2) . . . . ?
C28 C29 C33 C34 -58.3(3) . . . . ?
C24 C29 C33 C34 121.7(2) . . . . ?
C28 C29 C33 C35 63.9(3) . . . . ?
C24 C29 C33 C35 -116.1(2) . . . . ?
C5 C4 C36 N37 -84.6(3) . . . . ?
N3 C4 C36 N37 96.9(2) . . . . ?
C4 C36 N37 N38 -9.1(3) . . . . ?
C36 N37 N38 C39 178.45(18) . . . . ?
N37 N38 C39 C46 177.62(18) . . . . ?
N37 N38 C39 C40 -1.2(3) . . . . ?
N38 C39 C40 C41 16.3(4) . . . . ?
C46 C39 C40 C41 -162.4(2) . . . . ?
N38 C39 C40 C45 -161.5(2) . . . . ?
C46 C39 C40 C45 19.7(3) . . . . ?
C45 C40 C41 C42 -0.8(4) . . . . ?
C39 C40 C41 C42 -178.7(3) . . . . ?
C40 C41 C42 C43 -0.2(5) . . . . ?
C41 C42 C43 C44 0.9(5) . . . . ?
C42 C43 C44 C45 -0.7(4) . . . . ?
C43 C44 C45 C40 -0.3(4) . . . . ?
C41 C40 C45 C44 1.0(3) . . . . ?
C39 C40 C45 C44 179.0(2) . . . . ?
N38 C39 C46 O47 -164.3(2) . . . . ?
C40 C39 C46 O47 14.6(3) . . . . ?
N38 C39 C46 O48 15.9(3) . . . . ?
C40 C39 C46 O48 -165.23(18) . . . . ?
O47 C46 O48 C49 11.0(3) . . . . ?
C39 C46 O48 C49 -169.10(19) . . . . ?
C4 C5 C50 C51 -125.8(3) . . . . ?
N1 C5 C50 C51 56.4(3) . . . . ?
C4 C5 C50 C55 53.3(3) . . . . ?
N1 C5 C50 C55 -124.5(2) . . . . ?
C55 C50 C51 C52 0.3(4) . . . . ?
C5 C50 C51 C52 179.4(2) . . . . ?
C50 C51 C52 C53 0.7(4) . . . . ?
C51 C52 C53 C54 -1.3(5) . . . . ?
C52 C53 C54 C55 0.8(5) . . . . ?
C53 C54 C55 C50 0.2(4) . . . . ?
C51 C50 C55 C54 -0.8(4) . . . . ?
C5 C50 C55 C54 -179.9(2) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.049




####################################################################### 
# 
# 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_wl600_sq
_database_code_depnum_ccdc_archive 'CCDC 2243056'
loop_
_audit_author_name
_audit_author_address
'Qiuming Liang'
;University of Toronto
Canada
;
_audit_update_record             
;
2023-02-19 deposited with the CCDC.	2023-03-24 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            'C55 H58 N4 O2'
_chemical_formula_weight         807.05

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                   17.399(7)
_cell_length_b                   18.549(7)
_cell_length_c                   20.435(7)
_cell_angle_alpha                87.920(11)
_cell_angle_beta                 76.584(11)
_cell_angle_gamma                68.008(10)
_cell_volume                     5939(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    186168
_cell_measurement_theta_min      1.835
_cell_measurement_theta_max      27.751

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.903
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.055
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa Photon II'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            186168
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         27.751
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             27800
_reflns_number_gt                15856
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         27800
_refine_ls_number_parameters     1117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1128
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
N1 N 0.75474(8) 0.43586(7) 0.66738(6) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.76676(10) 0.40408(9) 0.60582(8) 0.0242(4) Uani 1 1 d . . . . .
N3 N 0.70117(8) 0.44812(7) 0.57991(6) 0.0236(3) Uani 1 1 d . . . . .
C4 C 0.64661(10) 0.51024(9) 0.62534(8) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.68010(10) 0.50270(9) 0.68025(8) 0.0239(4) Uani 1 1 d . . . . .
C6 C 0.79933(10) 0.39491(10) 0.71794(8) 0.0263(4) Uani 1 1 d . . . . .
C7 C 0.78525(11) 0.32855(10) 0.74185(8) 0.0320(4) Uani 1 1 d . . . . .
C8 C 0.82814(13) 0.29000(11) 0.79001(9) 0.0441(5) Uani 1 1 d . . . . .
H8 H 0.820235 0.244399 0.807344 0.053 Uiso 1 1 calc R U . . .
C9 C 0.88141(13) 0.31590(12) 0.81315(10) 0.0473(5) Uani 1 1 d . . . . .
H9 H 0.910220 0.288200 0.845955 0.057 Uiso 1 1 calc R U . . .
C10 C 0.89332(12) 0.38177(11) 0.78909(9) 0.0395(5) Uani 1 1 d . . . . .
H10 H 0.930009 0.399503 0.805977 0.047 Uiso 1 1 calc R U . . .
C11 C 0.85300(10) 0.42327(10) 0.74055(8) 0.0301(4) Uani 1 1 d . . . . .
C12 C 0.72510(12) 0.29744(10) 0.72004(9) 0.0379(4) Uani 1 1 d . . . . .
H12 H 0.709328 0.325232 0.679390 0.045 Uiso 1 1 calc R U . . .
C13 C 0.76825(15) 0.21084(12) 0.69971(12) 0.0602(6) Uani 1 1 d . . . . .
H13A H 0.731580 0.194652 0.678742 0.090 Uiso 1 1 calc R U . . .
H13B H 0.777920 0.181331 0.739766 0.090 Uiso 1 1 calc R U . . .
H13C H 0.823020 0.200789 0.667527 0.090 Uiso 1 1 calc R U . . .
C14 C 0.64385(15) 0.31473(15) 0.77384(11) 0.0676(7) Uani 1 1 d . . . . .
H14A H 0.606106 0.294768 0.758116 0.101 Uiso 1 1 calc R U . . .
H14B H 0.615291 0.371146 0.783417 0.101 Uiso 1 1 calc R U . . .
H14C H 0.657352 0.289531 0.814957 0.101 Uiso 1 1 calc R U . . .
C15 C 0.87052(11) 0.49453(10) 0.71580(9) 0.0343(4) Uani 1 1 d . . . . .
H15 H 0.838266 0.516786 0.680452 0.041 Uiso 1 1 calc R U . . .
C16 C 0.96526(11) 0.47503(12) 0.68526(10) 0.0442(5) Uani 1 1 d . . . . .
H16A H 0.973893 0.522113 0.668045 0.066 Uiso 1 1 calc R U . . .
H16B H 0.985305 0.435401 0.648234 0.066 Uiso 1 1 calc R U . . .
H16C H 0.997406 0.455065 0.719894 0.066 Uiso 1 1 calc R U . . .
C17 C 0.84061(13) 0.55648(11) 0.77378(10) 0.0453(5) Uani 1 1 d . . . . .
H17A H 0.848791 0.603627 0.756235 0.068 Uiso 1 1 calc R U . . .
H17B H 0.873914 0.536408 0.807687 0.068 Uiso 1 1 calc R U . . .
H17C H 0.780032 0.568935 0.794419 0.068 Uiso 1 1 calc R U . . .
C18 C 0.84113(10) 0.33633(10) 0.57308(8) 0.0285(4) Uani 1 1 d . . . . .
C19 C 0.92133(11) 0.33161(11) 0.57724(9) 0.0341(4) Uani 1 1 d . . . . .
H19 H 0.926285 0.371431 0.601935 0.041 Uiso 1 1 calc R U . . .
C20 C 0.99391(12) 0.27018(12) 0.54620(10) 0.0471(5) Uani 1 1 d . . . . .
H20 H 1.048638 0.267742 0.548772 0.057 Uiso 1 1 calc R U . . .
C21 C 0.98561(14) 0.21243(13) 0.51140(11) 0.0613(6) Uani 1 1 d . . . . .
H21 H 1.035103 0.169367 0.490344 0.074 Uiso 1 1 calc R U . . .
C22 C 0.90675(14) 0.21619(13) 0.50668(12) 0.0579(6) Uani 1 1 d . . . . .
H22 H 0.902096 0.175889 0.482396 0.070 Uiso 1 1 calc R U . . .
C23 C 0.83458(12) 0.27802(10) 0.53694(9) 0.0391(5) Uani 1 1 d . . . . .
H23 H 0.780192 0.280778 0.533072 0.047 Uiso 1 1 calc R U . . .
C24 C 0.68730(10) 0.42810(9) 0.51668(8) 0.0247(4) Uani 1 1 d . . . . .
C25 C 0.63030(10) 0.39067(9) 0.51932(8) 0.0274(4) Uani 1 1 d . . . . .
C26 C 0.62512(11) 0.36421(10) 0.45844(9) 0.0326(4) Uani 1 1 d . . . . .
H26 H 0.586504 0.339161 0.458256 0.039 Uiso 1 1 calc R U . . .
C27 C 0.67474(11) 0.37359(10) 0.39858(9) 0.0357(4) Uani 1 1 d . . . . .
H27 H 0.672071 0.352950 0.357654 0.043 Uiso 1 1 calc R U . . .
C28 C 0.72833(11) 0.41266(10) 0.39738(9) 0.0339(4) Uani 1 1 d . . . . .
H28 H 0.760832 0.420141 0.355319 0.041 Uiso 1 1 calc R U . . .
C29 C 0.73602(10) 0.44157(9) 0.45666(8) 0.0270(4) Uani 1 1 d . . . . .
C30 C 0.57509(10) 0.37770(10) 0.58424(9) 0.0309(4) Uani 1 1 d . . . . .
H30 H 0.586562 0.400798 0.622625 0.037 Uiso 1 1 calc R U . . .
C31 C 0.59655(12) 0.29081(10) 0.59442(10) 0.0411(5) Uani 1 1 d . . . . .
H31A H 0.657419 0.265116 0.593280 0.062 Uiso 1 1 calc R U . . .
H31B H 0.583152 0.267559 0.558395 0.062 Uiso 1 1 calc R U . . .
H31C H 0.562842 0.284101 0.638119 0.062 Uiso 1 1 calc R U . . .
C32 C 0.48048(11) 0.41788(10) 0.58532(9) 0.0366(4) Uani 1 1 d . . . . .
H32A H 0.467288 0.473227 0.577541 0.055 Uiso 1 1 calc R U . . .
H32B H 0.446274 0.412527 0.629263 0.055 Uiso 1 1 calc R U . . .
H32C H 0.467158 0.393686 0.549834 0.055 Uiso 1 1 calc R U . . .
C33 C 0.79416(11) 0.48502(10) 0.45253(9) 0.0333(4) Uani 1 1 d . . . . .
H33 H 0.789191 0.503869 0.499136 0.040 Uiso 1 1 calc R U . . .
C34 C 0.88722(11) 0.43199(12) 0.42318(10) 0.0461(5) Uani 1 1 d . . . . .
H34A H 0.902605 0.385676 0.449514 0.069 Uiso 1 1 calc R U . . .
H34B H 0.924407 0.460218 0.424994 0.069 Uiso 1 1 calc R U . . .
H34C H 0.894161 0.416165 0.376252 0.069 Uiso 1 1 calc R U . . .
C35 C 0.76882(13) 0.55539(11) 0.40996(9) 0.0417(5) Uani 1 1 d . . . . .
H35A H 0.708948 0.588638 0.428293 0.063 Uiso 1 1 calc R U . . .
H35B H 0.776290 0.537797 0.363440 0.063 Uiso 1 1 calc R U . . .
H35C H 0.804923 0.585006 0.410746 0.063 Uiso 1 1 calc R U . . .
C36 C 0.56966(10) 0.57098(9) 0.60872(8) 0.0250(4) Uani 1 1 d . . . . .
H36 H 0.550013 0.544466 0.578033 0.030 Uiso 1 1 calc R U . . .
C37 C 0.49624(10) 0.60237(9) 0.67033(8) 0.0264(4) Uani 1 1 d . . . . .
C38 C 0.46833(11) 0.55268(11) 0.71277(9) 0.0353(4) Uani 1 1 d . . . . .
H38 H 0.496048 0.497966 0.703736 0.042 Uiso 1 1 calc R U . . .
C39 C 0.40041(12) 0.58196(12) 0.76824(10) 0.0467(5) Uani 1 1 d . . . . .
H39 H 0.381935 0.547332 0.797075 0.056 Uiso 1 1 calc R U . . .
C40 C 0.35959(13) 0.66129(13) 0.78167(10) 0.0519(6) Uani 1 1 d . . . . .
H40 H 0.313372 0.681471 0.819947 0.062 Uiso 1 1 calc R U . . .
C41 C 0.38599(13) 0.71052(12) 0.73966(10) 0.0472(5) Uani 1 1 d . . . . .
H41 H 0.357565 0.765211 0.748513 0.057 Uiso 1 1 calc R U . . .
C42 C 0.45366(11) 0.68163(10) 0.68437(9) 0.0354(4) Uani 1 1 d . . . . .
H42 H 0.471221 0.716752 0.655538 0.042 Uiso 1 1 calc R U . . .
N43 N 0.58631(8) 0.63558(8) 0.57170(7) 0.0290(3) Uani 1 1 d . . . . .
N44 N 0.66313(8) 0.63059(8) 0.56801(7) 0.0272(3) Uani 1 1 d . . . . .
C45 C 0.68851(11) 0.68749(9) 0.54063(8) 0.0288(4) Uani 1 1 d . . . . .
C46 C 0.63573(11) 0.75972(9) 0.51493(8) 0.0295(4) Uani 1 1 d . . . . .
C47 C 0.64975(12) 0.82822(10) 0.51997(10) 0.0385(4) Uani 1 1 d . . . . .
H47 H 0.693256 0.828141 0.540792 0.046 Uiso 1 1 calc R U . . .
C48 C 0.60184(12) 0.89605(11) 0.49538(10) 0.0430(5) Uani 1 1 d . . . . .
H48 H 0.612758 0.941952 0.499563 0.052 Uiso 1 1 calc R U . . .
C49 C 0.53879(12) 0.89842(11) 0.46504(9) 0.0406(5) Uani 1 1 d . . . . .
H49 H 0.506677 0.945260 0.447483 0.049 Uiso 1 1 calc R U . . .
C50 C 0.52248(12) 0.83177(10) 0.46028(9) 0.0376(4) Uani 1 1 d . . . . .
H50 H 0.478259 0.832807 0.439912 0.045 Uiso 1 1 calc R U . . .
C51 C 0.57015(11) 0.76354(10) 0.48501(8) 0.0313(4) Uani 1 1 d . . . . .
H51 H 0.557959 0.718195 0.481538 0.038 Uiso 1 1 calc R U . . .
C52 C 0.77714(11) 0.67192(10) 0.53306(9) 0.0334(4) Uani 1 1 d . . . . .
O53 O 0.81626(8) 0.71133(7) 0.50528(7) 0.0457(3) Uani 1 1 d . . . . .
O54 O 0.82054(7) 0.60327(7) 0.55877(6) 0.0371(3) Uani 1 1 d . . . . .
C55 C 0.91025(12) 0.58313(12) 0.54426(11) 0.0521(6) Uani 1 1 d . . . . .
H55A H 0.937715 0.530213 0.557913 0.078 Uiso 1 1 calc R U . . .
H55B H 0.923074 0.619788 0.569069 0.078 Uiso 1 1 calc R U . . .
H55C H 0.931802 0.585505 0.495790 0.078 Uiso 1 1 calc R U . . .
C56 C 0.65116(10) 0.55510(10) 0.74107(8) 0.0278(4) Uani 1 1 d . . . . .
C57 C 0.63122(11) 0.53042(11) 0.80490(9) 0.0383(4) Uani 1 1 d . . . . .
H57 H 0.636966 0.477728 0.810581 0.046 Uiso 1 1 calc R U . . .
C58 C 0.60296(13) 0.58136(13) 0.86072(10) 0.0483(5) Uani 1 1 d . . . . .
H58 H 0.588572 0.563974 0.904497 0.058 Uiso 1 1 calc R U . . .
C59 C 0.59572(13) 0.65757(12) 0.85267(10) 0.0483(5) Uani 1 1 d . . . . .
H59 H 0.576904 0.692620 0.891018 0.058 Uiso 1 1 calc R U . . .
C60 C 0.61568(12) 0.68298(11) 0.78921(10) 0.0444(5) Uani 1 1 d . . . . .
H60 H 0.610576 0.735527 0.783707 0.053 Uiso 1 1 calc R U . . .
C61 C 0.64323(11) 0.63176(10) 0.73343(9) 0.0360(4) Uani 1 1 d . . . . .
H61 H 0.656766 0.649379 0.689614 0.043 Uiso 1 1 calc R U . . .
N62 N 0.74229(9) 0.89740(8) 0.17805(7) 0.0297(3) Uani 1 1 d . . . . .
C63 C 0.66277(10) 0.95209(9) 0.19255(8) 0.0274(4) Uani 1 1 d . . . . .
N64 N 0.62276(8) 0.94094(7) 0.14694(6) 0.0257(3) Uani 1 1 d . . . . .
C65 C 0.67757(10) 0.87748(9) 0.10290(8) 0.0265(4) Uani 1 1 d . . . . .
C66 C 0.75219(11) 0.84992(10) 0.12261(8) 0.0296(4) Uani 1 1 d . . . . .
C67 C 0.81285(11) 0.89800(11) 0.20447(9) 0.0349(4) Uani 1 1 d . . . . .
C68 C 0.84626(12) 0.84120(11) 0.24799(9) 0.0400(5) Uani 1 1 d . . . . .
C69 C 0.91829(13) 0.84102(13) 0.26643(11) 0.0528(6) Uani 1 1 d . . . . .
H69 H 0.943873 0.802370 0.294940 0.063 Uiso 1 1 calc R U . . .
C70 C 0.95325(14) 0.89468(14) 0.24479(12) 0.0576(6) Uani 1 1 d . . . . .
H70 H 1.002522 0.892912 0.258408 0.069 Uiso 1 1 calc R U . . .
C71 C 0.91820(13) 0.95110(13) 0.20364(11) 0.0541(6) Uani 1 1 d . . . . .
H71 H 0.942623 0.988824 0.189854 0.065 Uiso 1 1 calc R U . . .
C72 C 0.84674(12) 0.95393(11) 0.18159(10) 0.0413(5) Uani 1 1 d . . . . .
C73 C 0.80890(12) 0.78165(11) 0.27504(9) 0.0433(5) Uani 1 1 d . . . . .
H73 H 0.756215 0.791889 0.258464 0.052 Uiso 1 1 calc R U . . .
C74 C 0.78501(14) 0.78697(13) 0.35204(10) 0.0551(6) Uani 1 1 d . . . . .
H74A H 0.758902 0.749161 0.368340 0.083 Uiso 1 1 calc R U . . .
H74B H 0.744383 0.839608 0.368224 0.083 Uiso 1 1 calc R U . . .
H74C H 0.836419 0.775542 0.368946 0.083 Uiso 1 1 calc R U . . .
C75 C 0.87178(14) 0.69921(12) 0.25086(12) 0.0572(6) Uani 1 1 d . . . . .
H75A H 0.844361 0.662051 0.265961 0.086 Uiso 1 1 calc R U . . .
H75B H 0.921967 0.687052 0.269555 0.086 Uiso 1 1 calc R U . . .
H75C H 0.889372 0.695607 0.201537 0.086 Uiso 1 1 calc R U . . .
C76 C 0.81114(14) 1.01683(12) 0.13521(10) 0.0492(5) Uani 1 1 d . . . . .
H76 H 0.760916 1.009872 0.124686 0.059 Uiso 1 1 calc R U . . .
C77 C 0.77980(15) 1.09700(12) 0.17028(12) 0.0615(6) Uani 1 1 d . . . . .
H77A H 0.754628 1.136869 0.140395 0.092 Uiso 1 1 calc R U . . .
H77B H 0.827876 1.105401 0.181206 0.092 Uiso 1 1 calc R U . . .
H77C H 0.736712 1.100422 0.211846 0.092 Uiso 1 1 calc R U . . .
C78 C 0.87538(18) 1.01142(16) 0.06861(12) 0.0836(8) Uani 1 1 d . . . . .
H78A H 0.849055 1.052517 0.040103 0.125 Uiso 1 1 calc R U . . .
H78B H 0.892801 0.960427 0.045527 0.125 Uiso 1 1 calc R U . . .
H78C H 0.925510 1.017846 0.077469 0.125 Uiso 1 1 calc R U . . .
C79 C 0.62565(11) 1.01021(10) 0.24950(8) 0.0296(4) Uani 1 1 d . . . . .
C80 C 0.64713(11) 0.98973(10) 0.31037(8) 0.0347(4) Uani 1 1 d . . . . .
H80 H 0.686539 0.938947 0.314560 0.042 Uiso 1 1 calc R U . . .
C81 C 0.61181(12) 1.04242(11) 0.36488(9) 0.0408(5) Uani 1 1 d . . . . .
H81 H 0.627756 1.027937 0.406305 0.049 Uiso 1 1 calc R U . . .
C82 C 0.55398(12) 1.11548(10) 0.36032(9) 0.0377(4) Uani 1 1 d . . . . .
H82 H 0.529176 1.151325 0.398470 0.045 Uiso 1 1 calc R U . . .
C83 C 0.53207(12) 1.13654(10) 0.29981(9) 0.0366(4) Uani 1 1 d . . . . .
H83 H 0.492175 1.187291 0.296238 0.044 Uiso 1 1 calc R U . . .
C84 C 0.56731(11) 1.08496(10) 0.24483(9) 0.0322(4) Uani 1 1 d . . . . .
H84 H 0.551952 1.100154 0.203303 0.039 Uiso 1 1 calc R U . . .
C85 C 0.53711(10) 0.99149(9) 0.14285(8) 0.0254(4) Uani 1 1 d . . . . .
C86 C 0.46804(11) 0.98282(10) 0.18757(8) 0.0286(4) Uani 1 1 d . . . . .
C87 C 0.38794(11) 1.03855(10) 0.18780(9) 0.0339(4) Uani 1 1 d . . . . .
H87 H 0.339192 1.034704 0.217874 0.041 Uiso 1 1 calc R U . . .
C88 C 0.37750(11) 1.09890(10) 0.14574(9) 0.0340(4) Uani 1 1 d . . . . .
H88 H 0.322179 1.137095 0.147822 0.041 Uiso 1 1 calc R U . . .
C89 C 0.44653(11) 1.10428(10) 0.10078(9) 0.0329(4) Uani 1 1 d . . . . .
H89 H 0.438202 1.145430 0.070839 0.039 Uiso 1 1 calc R U . . .
C90 C 0.52863(11) 1.05088(9) 0.09791(8) 0.0276(4) Uani 1 1 d . . . . .
C91 C 0.47652(12) 0.91785(10) 0.23546(9) 0.0359(4) Uani 1 1 d . . . . .
H91 H 0.537677 0.881570 0.225883 0.043 Uiso 1 1 calc R U . . .
C92 C 0.44970(13) 0.95006(12) 0.30873(9) 0.0476(5) Uani 1 1 d . . . . .
H92A H 0.482990 0.980843 0.314554 0.071 Uiso 1 1 calc R U . . .
H92B H 0.460068 0.906762 0.338731 0.071 Uiso 1 1 calc R U . . .
H92C H 0.388874 0.983166 0.319769 0.071 Uiso 1 1 calc R U . . .
C93 C 0.42276(12) 0.87222(11) 0.22519(10) 0.0463(5) Uani 1 1 d . . . . .
H93A H 0.439024 0.853182 0.177935 0.069 Uiso 1 1 calc R U . . .
H93B H 0.362257 0.906280 0.236930 0.069 Uiso 1 1 calc R U . . .
H93C H 0.432487 0.827919 0.254121 0.069 Uiso 1 1 calc R U . . .
C94 C 0.60325(11) 1.06050(10) 0.04827(8) 0.0332(4) Uani 1 1 d . . . . .
H94 H 0.656644 1.016894 0.053005 0.040 Uiso 1 1 calc R U . . .
C95 C 0.61133(13) 1.13739(11) 0.06269(10) 0.0463(5) Uani 1 1 d . . . . .
H95A H 0.618474 1.139230 0.108697 0.069 Uiso 1 1 calc R U . . .
H95B H 0.559701 1.180959 0.057952 0.069 Uiso 1 1 calc R U . . .
H95C H 0.660991 1.141218 0.030647 0.069 Uiso 1 1 calc R U . . .
C96 C 0.59463(13) 1.05599(11) -0.02398(9) 0.0406(5) Uani 1 1 d . . . . .
H96A H 0.590077 1.006387 -0.033001 0.061 Uiso 1 1 calc R U . . .
H96B H 0.644917 1.059552 -0.055323 0.061 Uiso 1 1 calc R U . . .
H96C H 0.543351 1.099129 -0.029994 0.061 Uiso 1 1 calc R U . . .
C97 C 0.64885(10) 0.85222(9) 0.04720(8) 0.0266(4) Uani 1 1 d . . . . .
H97 H 0.606950 0.900630 0.033633 0.032 Uiso 1 1 calc R U . . .
C98 C 0.72139(11) 0.81968(10) -0.01535(8) 0.0299(4) Uani 1 1 d . . . . .
C99 C 0.77251(12) 0.85991(11) -0.04266(9) 0.0400(5) Uani 1 1 d . . . . .
H99 H 0.762938 0.908468 -0.021840 0.048 Uiso 1 1 calc R U . . .
C100 C 0.83750(13) 0.83090(14) -0.09981(10) 0.0531(6) Uani 1 1 d . . . . .
H100 H 0.872963 0.858833 -0.117520 0.064 Uiso 1 1 calc R U . . .
C101 C 0.85047(14) 0.76203(14) -0.13065(11) 0.0590(6) Uani 1 1 d . . . . .
H101 H 0.894843 0.742150 -0.170145 0.071 Uiso 1 1 calc R U . . .
C102 C 0.79994(14) 0.72140(13) -0.10503(10) 0.0551(6) Uani 1 1 d . . . . .
H102 H 0.809175 0.673458 -0.126765 0.066 Uiso 1 1 calc R U . . .
C103 C 0.73544(12) 0.75003(11) -0.04753(9) 0.0412(5) Uani 1 1 d . . . . .
H103 H 0.700457 0.721612 -0.029949 0.049 Uiso 1 1 calc R U . . .
N104 N 0.60344(9) 0.79914(8) 0.06601(7) 0.0321(3) Uani 1 1 d . . . . .
N105 N 0.61462(9) 0.76937(8) 0.12266(7) 0.0305(3) Uani 1 1 d . . . . .
C106 C 0.58657(11) 0.71276(10) 0.14504(8) 0.0326(4) Uani 1 1 d . . . . .
C107 C 0.54762(12) 0.67358(10) 0.10906(8) 0.0340(4) Uani 1 1 d . . . . .
C108 C 0.55890(13) 0.59605(11) 0.11891(9) 0.0427(5) Uani 1 1 d . . . . .
H108 H 0.593157 0.568171 0.148518 0.051 Uiso 1 1 calc R U . . .
C109 C 0.52161(14) 0.55854(12) 0.08677(10) 0.0499(5) Uani 1 1 d . . . . .
H109 H 0.530245 0.505615 0.094813 0.060 Uiso 1 1 calc R U . . .
C110 C 0.47242(14) 0.59670(12) 0.04354(10) 0.0498(5) Uani 1 1 d . . . . .
H110 H 0.446326 0.571011 0.021745 0.060 Uiso 1 1 calc R U . . .
C111 C 0.46148(15) 0.67291(12) 0.03223(10) 0.0508(6) Uani 1 1 d . . . . .
H111 H 0.427819 0.700019 0.001994 0.061 Uiso 1 1 calc R U . . .
C112 C 0.49854(13) 0.71067(11) 0.06406(9) 0.0416(5) Uani 1 1 d . . . . .
H112 H 0.490338 0.763309 0.055021 0.050 Uiso 1 1 calc R U . . .
C113 C 0.59537(12) 0.69158(11) 0.21214(9) 0.0374(4) Uani 1 1 d . . . . .
O114 O 0.57118(10) 0.64443(8) 0.24492(6) 0.0542(4) Uani 1 1 d . . . . .
O115 O 0.63177(8) 0.73189(8) 0.24073(6) 0.0446(3) Uani 1 1 d . . . . .
C116 C 0.63171(15) 0.71831(15) 0.31005(9) 0.0613(6) Uani 1 1 d . . . . .
H11A H 0.649826 0.755655 0.328571 0.092 Uiso 1 1 calc R U . . .
H11B H 0.671201 0.665209 0.313831 0.092 Uiso 1 1 calc R U . . .
H11C H 0.574073 0.724748 0.335259 0.092 Uiso 1 1 calc R U . . .
C117 C 0.83052(11) 0.78207(10) 0.09570(9) 0.0363(4) Uani 1 1 d . . . . .
C118 C 0.90984(12) 0.78728(12) 0.07618(10) 0.0483(5) Uani 1 1 d . . . . .
H118 H 0.915234 0.835580 0.082124 0.058 Uiso 1 1 calc R U . . .
C119 C 0.98094(14) 0.72312(15) 0.04825(12) 0.0665(7) Uani 1 1 d . . . . .
H119 H 1.034981 0.727496 0.034465 0.080 Uiso 1 1 calc R U . . .
C120 C 0.97412(15) 0.65293(15) 0.04023(13) 0.0744(8) Uani 1 1 d . . . . .
H120 H 1.023447 0.608512 0.021516 0.089 Uiso 1 1 calc R U . . .
C121 C 0.89623(16) 0.64697(13) 0.05920(13) 0.0699(7) Uani 1 1 d . . . . .
H121 H 0.891413 0.598440 0.053074 0.084 Uiso 1 1 calc R U . . .
C122 C 0.82398(13) 0.71142(11) 0.08739(10) 0.0500(5) Uani 1 1 d . . . . .
H122 H 0.770064 0.706753 0.100930 0.060 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
N1 C2 1.346(2) . ?
N1 C5 1.397(2) . ?
N1 C6 1.456(2) . ?
C2 N3 1.3420(19) . ?
C2 C18 1.464(2) . ?
N3 C4 1.393(2) . ?
N3 C24 1.454(2) . ?
C4 C5 1.360(2) . ?
C4 C36 1.493(2) . ?
C5 C56 1.474(2) . ?
C6 C7 1.393(2) . ?
C6 C11 1.396(2) . ?
C7 C8 1.388(2) . ?
C7 C12 1.521(3) . ?
C8 C9 1.366(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.370(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C15 1.509(2) . ?
C12 C14 1.508(3) . ?
C12 C13 1.522(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.526(3) . ?
C15 C17 1.536(2) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.385(2) . ?
C18 C19 1.387(2) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.374(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C29 1.393(2) . ?
C24 C25 1.399(2) . ?
C25 C26 1.388(2) . ?
C25 C30 1.516(2) . ?
C26 C27 1.371(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.375(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.396(2) . ?
C28 H28 0.9500 . ?
C29 C33 1.499(2) . ?
C30 C32 1.527(2) . ?
C30 C31 1.530(2) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C35 1.523(2) . ?
C33 C34 1.532(3) . ?
C33 H33 1.0000 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N43 1.478(2) . ?
C36 C37 1.519(2) . ?
C36 H36 1.0000 . ?
C37 C42 1.382(2) . ?
C37 C38 1.385(2) . ?
C38 C39 1.385(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.379(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.362(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.380(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
N43 N44 1.2890(19) . ?
N44 C45 1.347(2) . ?
C45 C52 1.430(2) . ?
C45 C46 1.471(2) . ?
C46 C47 1.392(2) . ?
C46 C51 1.393(2) . ?
C47 C48 1.376(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.366(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.379(2) . ?
C49 H49 0.9500 . ?
C50 C51 1.381(2) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 O53 1.218(2) . ?
C52 O54 1.372(2) . ?
O54 C55 1.421(2) . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 C57 1.377(2) . ?
C56 C61 1.383(2) . ?
C57 C58 1.381(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.379(3) . ?
C58 H58 0.9500 . ?
C59 C60 1.376(3) . ?
C59 H59 0.9500 . ?
C60 C61 1.384(2) . ?
C60 H60 0.9500 . ?
C61 H61 0.9500 . ?
N62 C63 1.346(2) . ?
N62 C66 1.399(2) . ?
N62 C67 1.455(2) . ?
C63 N64 1.349(2) . ?
C63 C79 1.468(2) . ?
N64 C65 1.394(2) . ?
N64 C85 1.453(2) . ?
C65 C66 1.356(2) . ?
C65 C97 1.497(2) . ?
C66 C117 1.470(2) . ?
C67 C72 1.392(3) . ?
C67 C68 1.397(3) . ?
C68 C69 1.389(3) . ?
C68 C73 1.508(3) . ?
C69 C70 1.361(3) . ?
C69 H69 0.9500 . ?
C70 C71 1.368(3) . ?
C70 H70 0.9500 . ?
C71 C72 1.400(3) . ?
C71 H71 0.9500 . ?
C72 C76 1.514(3) . ?
C73 C75 1.527(3) . ?
C73 C74 1.528(3) . ?
C73 H73 1.0000 . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 0.9800 . ?
C75 H75A 0.9800 . ?
C75 H75B 0.9800 . ?
C75 H75C 0.9800 . ?
C76 C77 1.520(3) . ?
C76 C78 1.527(3) . ?
C76 H76 1.0000 . ?
C77 H77A 0.9800 . ?
C77 H77B 0.9800 . ?
C77 H77C 0.9800 . ?
C78 H78A 0.9800 . ?
C78 H78B 0.9800 . ?
C78 H78C 0.9800 . ?
C79 C80 1.381(2) . ?
C79 C84 1.394(2) . ?
C80 C81 1.373(2) . ?
C80 H80 0.9500 . ?
C81 C82 1.368(3) . ?
C81 H81 0.9500 . ?
C82 C83 1.378(2) . ?
C82 H82 0.9500 . ?
C83 C84 1.369(2) . ?
C83 H83 0.9500 . ?
C84 H84 0.9500 . ?
C85 C86 1.389(2) . ?
C85 C90 1.395(2) . ?
C86 C87 1.389(2) . ?
C86 C91 1.510(2) . ?
C87 C88 1.369(2) . ?
C87 H87 0.9500 . ?
C88 C89 1.367(2) . ?
C88 H88 0.9500 . ?
C89 C90 1.389(2) . ?
C89 H89 0.9500 . ?
C90 C94 1.515(2) . ?
C91 C93 1.527(3) . ?
C91 C92 1.532(3) . ?
C91 H91 1.0000 . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
C93 H93A 0.9800 . ?
C93 H93B 0.9800 . ?
C93 H93C 0.9800 . ?
C94 C96 1.526(2) . ?
C94 C95 1.530(2) . ?
C94 H94 1.0000 . ?
C95 H95A 0.9800 . ?
C95 H95B 0.9800 . ?
C95 H95C 0.9800 . ?
C96 H96A 0.9800 . ?
C96 H96B 0.9800 . ?
C96 H96C 0.9800 . ?
C97 N104 1.468(2) . ?
C97 C98 1.526(2) . ?
C97 H97 1.0000 . ?
C98 C99 1.377(2) . ?
C98 C103 1.383(2) . ?
C99 C100 1.382(3) . ?
C99 H99 0.9500 . ?
C100 C101 1.362(3) . ?
C100 H100 0.9500 . ?
C101 C102 1.367(3) . ?
C101 H101 0.9500 . ?
C102 C103 1.382(3) . ?
C102 H102 0.9500 . ?
C103 H103 0.9500 . ?
N104 N105 1.2886(18) . ?
N105 C106 1.340(2) . ?
C106 C113 1.439(2) . ?
C106 C107 1.472(2) . ?
C107 C112 1.388(3) . ?
C107 C108 1.390(2) . ?
C108 C109 1.380(3) . ?
C108 H108 0.9500 . ?
C109 C110 1.366(3) . ?
C109 H109 0.9500 . ?
C110 C111 1.372(3) . ?
C110 H110 0.9500 . ?
C111 C112 1.377(3) . ?
C111 H111 0.9500 . ?
C112 H112 0.9500 . ?
C113 O114 1.222(2) . ?
C113 O115 1.364(2) . ?
O115 C116 1.429(2) . ?
C116 H11A 0.9800 . ?
C116 H11B 0.9800 . ?
C116 H11C 0.9800 . ?
C117 C122 1.377(3) . ?
C117 C118 1.384(3) . ?
C118 C119 1.375(3) . ?
C118 H118 0.9500 . ?
C119 C120 1.370(3) . ?
C119 H119 0.9500 . ?
C120 C121 1.365(3) . ?
C120 H120 0.9500 . ?
C121 C122 1.389(3) . ?
C121 H121 0.9500 . ?
C122 H122 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 109.24(13) . . ?
C2 N1 C6 123.57(13) . . ?
C5 N1 C6 125.20(13) . . ?
N3 C2 N1 107.49(14) . . ?
N3 C2 C18 127.41(14) . . ?
N1 C2 C18 125.01(14) . . ?
C2 N3 C4 109.58(13) . . ?
C2 N3 C24 123.68(13) . . ?
C4 N3 C24 126.51(13) . . ?
C5 C4 N3 106.86(13) . . ?
C5 C4 C36 131.65(15) . . ?
N3 C4 C36 121.46(13) . . ?
C4 C5 N1 106.82(14) . . ?
C4 C5 C56 129.45(15) . . ?
N1 C5 C56 123.58(14) . . ?
C7 C6 C11 123.08(15) . . ?
C7 C6 N1 117.33(14) . . ?
C11 C6 N1 119.59(15) . . ?
C8 C7 C6 116.81(17) . . ?
C8 C7 C12 118.66(16) . . ?
C6 C7 C12 124.51(15) . . ?
C9 C8 C7 121.74(19) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.05(18) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 121.56(18) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C6 116.76(16) . . ?
C10 C11 C15 118.37(16) . . ?
C6 C11 C15 124.87(15) . . ?
C14 C12 C7 111.34(16) . . ?
C14 C12 C13 111.30(18) . . ?
C7 C12 C13 111.59(16) . . ?
C14 C12 H12 107.5 . . ?
C7 C12 H12 107.5 . . ?
C13 C12 H12 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 111.76(15) . . ?
C11 C15 C17 110.58(15) . . ?
C16 C15 C17 108.55(15) . . ?
C11 C15 H15 108.6 . . ?
C16 C15 H15 108.6 . . ?
C17 C15 H15 108.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 118.98(16) . . ?
C23 C18 C2 122.58(15) . . ?
C19 C18 C2 118.42(16) . . ?
C20 C19 C18 121.15(18) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 118.74(19) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C22 C21 C20 120.89(19) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 119.98(18) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C29 C24 C25 123.30(14) . . ?
C29 C24 N3 118.52(14) . . ?
C25 C24 N3 117.99(14) . . ?
C26 C25 C24 117.09(15) . . ?
C26 C25 C30 119.12(15) . . ?
C24 C25 C30 123.78(15) . . ?
C27 C26 C25 121.17(16) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 120.41(16) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C29 121.42(16) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C24 C29 C28 116.52(15) . . ?
C24 C29 C33 124.16(14) . . ?
C28 C29 C33 119.32(15) . . ?
C25 C30 C32 111.15(14) . . ?
C25 C30 C31 111.24(15) . . ?
C32 C30 C31 109.69(14) . . ?
C25 C30 H30 108.2 . . ?
C32 C30 H30 108.2 . . ?
C31 C30 H30 108.2 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C33 C35 110.94(14) . . ?
C29 C33 C34 111.04(15) . . ?
C35 C33 C34 109.65(15) . . ?
C29 C33 H33 108.4 . . ?
C35 C33 H33 108.4 . . ?
C34 C33 H33 108.4 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N43 C36 C4 114.27(13) . . ?
N43 C36 C37 110.54(13) . . ?
C4 C36 C37 112.33(13) . . ?
N43 C36 H36 106.4 . . ?
C4 C36 H36 106.4 . . ?
C37 C36 H36 106.4 . . ?
C42 C37 C38 118.15(16) . . ?
C42 C37 C36 120.67(15) . . ?
C38 C37 C36 121.15(15) . . ?
C39 C38 C37 120.68(17) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C38 120.11(18) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C41 C40 C39 119.54(19) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C40 C41 C42 120.57(19) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 C37 120.95(18) . . ?
C41 C42 H42 119.5 . . ?
C37 C42 H42 119.5 . . ?
N44 N43 C36 111.00(13) . . ?
N43 N44 C45 119.91(14) . . ?
N44 C45 C52 114.82(15) . . ?
N44 C45 C46 126.51(15) . . ?
C52 C45 C46 118.56(15) . . ?
C47 C46 C51 116.90(16) . . ?
C47 C46 C45 120.47(15) . . ?
C51 C46 C45 122.63(15) . . ?
C48 C47 C46 121.29(17) . . ?
C48 C47 H47 119.4 . . ?
C46 C47 H47 119.4 . . ?
C49 C48 C47 121.05(18) . . ?
C49 C48 H48 119.5 . . ?
C47 C48 H48 119.5 . . ?
C48 C49 C50 118.99(17) . . ?
C48 C49 H49 120.5 . . ?
C50 C49 H49 120.5 . . ?
C49 C50 C51 120.28(17) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
C50 C51 C46 121.48(17) . . ?
C50 C51 H51 119.3 . . ?
C46 C51 H51 119.3 . . ?
O53 C52 O54 118.96(16) . . ?
O53 C52 C45 127.05(16) . . ?
O54 C52 C45 113.96(15) . . ?
C52 O54 C55 114.01(14) . . ?
O54 C55 H55A 109.5 . . ?
O54 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
O54 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C57 C56 C61 119.14(16) . . ?
C57 C56 C5 122.25(16) . . ?
C61 C56 C5 118.61(15) . . ?
C56 C57 C58 120.75(18) . . ?
C56 C57 H57 119.6 . . ?
C58 C57 H57 119.6 . . ?
C59 C58 C57 119.72(19) . . ?
C59 C58 H58 120.1 . . ?
C57 C58 H58 120.1 . . ?
C60 C59 C58 120.15(18) . . ?
C60 C59 H59 119.9 . . ?
C58 C59 H59 119.9 . . ?
C59 C60 C61 119.82(19) . . ?
C59 C60 H60 120.1 . . ?
C61 C60 H60 120.1 . . ?
C56 C61 C60 120.42(18) . . ?
C56 C61 H61 119.8 . . ?
C60 C61 H61 119.8 . . ?
C63 N62 C66 109.26(13) . . ?
C63 N62 C67 125.44(14) . . ?
C66 N62 C67 123.82(14) . . ?
N62 C63 N64 107.13(14) . . ?
N62 C63 C79 126.11(14) . . ?
N64 C63 C79 126.69(15) . . ?
C63 N64 C65 109.82(13) . . ?
C63 N64 C85 124.03(13) . . ?
C65 N64 C85 126.04(13) . . ?
C66 C65 N64 106.58(14) . . ?
C66 C65 C97 132.61(15) . . ?
N64 C65 C97 120.81(14) . . ?
C65 C66 N62 107.19(14) . . ?
C65 C66 C117 129.63(15) . . ?
N62 C66 C117 123.14(15) . . ?
C72 C67 C68 123.14(17) . . ?
C72 C67 N62 117.12(16) . . ?
C68 C67 N62 119.66(17) . . ?
C69 C68 C67 116.54(19) . . ?
C69 C68 C73 119.50(18) . . ?
C67 C68 C73 123.96(17) . . ?
C70 C69 C68 121.8(2) . . ?
C70 C69 H69 119.1 . . ?
C68 C69 H69 119.1 . . ?
C69 C70 C71 120.7(2) . . ?
C69 C70 H70 119.7 . . ?
C71 C70 H70 119.7 . . ?
C70 C71 C72 120.8(2) . . ?
C70 C71 H71 119.6 . . ?
C72 C71 H71 119.6 . . ?
C67 C72 C71 116.96(19) . . ?
C67 C72 C76 124.27(17) . . ?
C71 C72 C76 118.77(19) . . ?
C68 C73 C75 111.09(17) . . ?
C68 C73 C74 111.03(17) . . ?
C75 C73 C74 108.66(17) . . ?
C68 C73 H73 108.7 . . ?
C75 C73 H73 108.7 . . ?
C74 C73 H73 108.7 . . ?
C73 C74 H74A 109.5 . . ?
C73 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
C73 C75 H75A 109.5 . . ?
C73 C75 H75B 109.5 . . ?
H75A C75 H75B 109.5 . . ?
C73 C75 H75C 109.5 . . ?
H75A C75 H75C 109.5 . . ?
H75B C75 H75C 109.5 . . ?
C72 C76 C77 110.50(17) . . ?
C72 C76 C78 112.57(19) . . ?
C77 C76 C78 110.39(19) . . ?
C72 C76 H76 107.7 . . ?
C77 C76 H76 107.7 . . ?
C78 C76 H76 107.7 . . ?
C76 C77 H77A 109.5 . . ?
C76 C77 H77B 109.5 . . ?
H77A C77 H77B 109.5 . . ?
C76 C77 H77C 109.5 . . ?
H77A C77 H77C 109.5 . . ?
H77B C77 H77C 109.5 . . ?
C76 C78 H78A 109.5 . . ?
C76 C78 H78B 109.5 . . ?
H78A C78 H78B 109.5 . . ?
C76 C78 H78C 109.5 . . ?
H78A C78 H78C 109.5 . . ?
H78B C78 H78C 109.5 . . ?
C80 C79 C84 118.67(16) . . ?
C80 C79 C63 119.14(15) . . ?
C84 C79 C63 122.16(15) . . ?
C81 C80 C79 120.32(17) . . ?
C81 C80 H80 119.8 . . ?
C79 C80 H80 119.8 . . ?
C82 C81 C80 120.88(17) . . ?
C82 C81 H81 119.6 . . ?
C80 C81 H81 119.6 . . ?
C81 C82 C83 119.29(17) . . ?
C81 C82 H82 120.4 . . ?
C83 C82 H82 120.4 . . ?
C84 C83 C82 120.55(17) . . ?
C84 C83 H83 119.7 . . ?
C82 C83 H83 119.7 . . ?
C83 C84 C79 120.28(16) . . ?
C83 C84 H84 119.9 . . ?
C79 C84 H84 119.9 . . ?
C86 C85 C90 123.13(15) . . ?
C86 C85 N64 118.73(14) . . ?
C90 C85 N64 117.90(14) . . ?
C87 C86 C85 116.76(15) . . ?
C87 C86 C91 119.75(16) . . ?
C85 C86 C91 123.48(15) . . ?
C88 C87 C86 121.64(17) . . ?
C88 C87 H87 119.2 . . ?
C86 C87 H87 119.2 . . ?
C89 C88 C87 120.10(16) . . ?
C89 C88 H88 120.0 . . ?
C87 C88 H88 120.0 . . ?
C88 C89 C90 121.45(16) . . ?
C88 C89 H89 119.3 . . ?
C90 C89 H89 119.3 . . ?
C89 C90 C85 116.85(16) . . ?
C89 C90 C94 119.40(15) . . ?
C85 C90 C94 123.73(15) . . ?
C86 C91 C93 110.61(15) . . ?
C86 C91 C92 110.79(15) . . ?
C93 C91 C92 109.92(15) . . ?
C86 C91 H91 108.5 . . ?
C93 C91 H91 108.5 . . ?
C92 C91 H91 108.5 . . ?
C91 C92 H92A 109.5 . . ?
C91 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
C91 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
C91 C93 H93A 109.5 . . ?
C91 C93 H93B 109.5 . . ?
H93A C93 H93B 109.5 . . ?
C91 C93 H93C 109.5 . . ?
H93A C93 H93C 109.5 . . ?
H93B C93 H93C 109.5 . . ?
C90 C94 C96 110.80(14) . . ?
C90 C94 C95 111.41(15) . . ?
C96 C94 C95 109.92(14) . . ?
C90 C94 H94 108.2 . . ?
C96 C94 H94 108.2 . . ?
C95 C94 H94 108.2 . . ?
C94 C95 H95A 109.5 . . ?
C94 C95 H95B 109.5 . . ?
H95A C95 H95B 109.5 . . ?
C94 C95 H95C 109.5 . . ?
H95A C95 H95C 109.5 . . ?
H95B C95 H95C 109.5 . . ?
C94 C96 H96A 109.5 . . ?
C94 C96 H96B 109.5 . . ?
H96A C96 H96B 109.5 . . ?
C94 C96 H96C 109.5 . . ?
H96A C96 H96C 109.5 . . ?
H96B C96 H96C 109.5 . . ?
N104 C97 C65 115.30(13) . . ?
N104 C97 C98 110.84(13) . . ?
C65 C97 C98 112.12(14) . . ?
N104 C97 H97 105.9 . . ?
C65 C97 H97 105.9 . . ?
C98 C97 H97 105.9 . . ?
C99 C98 C103 118.23(17) . . ?
C99 C98 C97 121.17(15) . . ?
C103 C98 C97 120.55(16) . . ?
C98 C99 C100 121.16(19) . . ?
C98 C99 H99 119.4 . . ?
C100 C99 H99 119.4 . . ?
C101 C100 C99 119.7(2) . . ?
C101 C100 H100 120.2 . . ?
C99 C100 H100 120.2 . . ?
C100 C101 C102 120.3(2) . . ?
C100 C101 H101 119.8 . . ?
C102 C101 H101 119.8 . . ?
C101 C102 C103 120.0(2) . . ?
C101 C102 H102 120.0 . . ?
C103 C102 H102 120.0 . . ?
C102 C103 C98 120.57(19) . . ?
C102 C103 H103 119.7 . . ?
C98 C103 H103 119.7 . . ?
N105 N104 C97 111.15(13) . . ?
N104 N105 C106 120.44(14) . . ?
N105 C106 C113 113.80(15) . . ?
N105 C106 C107 126.90(15) . . ?
C113 C106 C107 119.28(16) . . ?
C112 C107 C108 116.48(17) . . ?
C112 C107 C106 122.86(16) . . ?
C108 C107 C106 120.66(17) . . ?
C109 C108 C107 121.7(2) . . ?
C109 C108 H108 119.2 . . ?
C107 C108 H108 119.2 . . ?
C110 C109 C108 120.71(19) . . ?
C110 C109 H109 119.6 . . ?
C108 C109 H109 119.6 . . ?
C109 C110 C111 118.61(19) . . ?
C109 C110 H110 120.7 . . ?
C111 C110 H110 120.7 . . ?
C110 C111 C112 121.0(2) . . ?
C110 C111 H111 119.5 . . ?
C112 C111 H111 119.5 . . ?
C111 C112 C107 121.49(18) . . ?
C111 C112 H112 119.3 . . ?
C107 C112 H112 119.3 . . ?
O114 C113 O115 119.21(16) . . ?
O114 C113 C106 126.51(18) . . ?
O115 C113 C106 114.23(16) . . ?
C113 O115 C116 114.87(15) . . ?
O115 C116 H11A 109.5 . . ?
O115 C116 H11B 109.5 . . ?
H11A C116 H11B 109.5 . . ?
O115 C116 H11C 109.5 . . ?
H11A C116 H11C 109.5 . . ?
H11B C116 H11C 109.5 . . ?
C122 C117 C118 118.96(18) . . ?
C122 C117 C66 118.54(17) . . ?
C118 C117 C66 122.45(17) . . ?
C119 C118 C117 120.6(2) . . ?
C119 C118 H118 119.7 . . ?
C117 C118 H118 119.7 . . ?
C120 C119 C118 120.2(2) . . ?
C120 C119 H119 119.9 . . ?
C118 C119 H119 119.9 . . ?
C121 C120 C119 119.8(2) . . ?
C121 C120 H120 120.1 . . ?
C119 C120 H120 120.1 . . ?
C120 C121 C122 120.4(2) . . ?
C120 C121 H121 119.8 . . ?
C122 C121 H121 119.8 . . ?
C117 C122 C121 120.0(2) . . ?
C117 C122 H122 120.0 . . ?
C121 C122 H122 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C2 N3 -1.03(17) . . . . ?
C6 N1 C2 N3 163.65(13) . . . . ?
C5 N1 C2 C18 175.82(14) . . . . ?
C6 N1 C2 C18 -19.5(2) . . . . ?
N1 C2 N3 C4 1.01(17) . . . . ?
C18 C2 N3 C4 -175.75(15) . . . . ?
N1 C2 N3 C24 -173.82(13) . . . . ?
C18 C2 N3 C24 9.4(2) . . . . ?
C2 N3 C4 C5 -0.59(17) . . . . ?
C24 N3 C4 C5 174.05(14) . . . . ?
C2 N3 C4 C36 177.44(14) . . . . ?
C24 N3 C4 C36 -7.9(2) . . . . ?
N3 C4 C5 N1 -0.05(16) . . . . ?
C36 C4 C5 N1 -177.80(15) . . . . ?
N3 C4 C5 C56 175.61(15) . . . . ?
C36 C4 C5 C56 -2.1(3) . . . . ?
C2 N1 C5 C4 0.67(17) . . . . ?
C6 N1 C5 C4 -163.70(14) . . . . ?
C2 N1 C5 C56 -175.31(14) . . . . ?
C6 N1 C5 C56 20.3(2) . . . . ?
C2 N1 C6 C7 -62.8(2) . . . . ?
C5 N1 C6 C7 99.43(19) . . . . ?
C2 N1 C6 C11 117.64(17) . . . . ?
C5 N1 C6 C11 -80.1(2) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
N1 C6 C7 C8 179.97(15) . . . . ?
C11 C6 C7 C12 177.96(16) . . . . ?
N1 C6 C7 C12 -1.6(2) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C12 C7 C8 C9 -178.31(18) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C6 0.5(3) . . . . ?
C9 C10 C11 C15 -179.03(17) . . . . ?
C7 C6 C11 C10 0.1(2) . . . . ?
N1 C6 C11 C10 179.67(15) . . . . ?
C7 C6 C11 C15 179.61(16) . . . . ?
N1 C6 C11 C15 -0.9(2) . . . . ?
C8 C7 C12 C14 73.6(2) . . . . ?
C6 C7 C12 C14 -104.8(2) . . . . ?
C8 C7 C12 C13 -51.4(2) . . . . ?
C6 C7 C12 C13 130.19(19) . . . . ?
C10 C11 C15 C16 58.7(2) . . . . ?
C6 C11 C15 C16 -120.79(18) . . . . ?
C10 C11 C15 C17 -62.4(2) . . . . ?
C6 C11 C15 C17 118.16(18) . . . . ?
N3 C2 C18 C23 -44.9(3) . . . . ?
N1 C2 C18 C23 138.90(17) . . . . ?
N3 C2 C18 C19 133.55(17) . . . . ?
N1 C2 C18 C19 -42.7(2) . . . . ?
C23 C18 C19 C20 0.0(3) . . . . ?
C2 C18 C19 C20 -178.53(16) . . . . ?
C18 C19 C20 C21 -0.9(3) . . . . ?
C19 C20 C21 C22 0.9(3) . . . . ?
C20 C21 C22 C23 -0.1(4) . . . . ?
C21 C22 C23 C18 -0.8(3) . . . . ?
C19 C18 C23 C22 0.9(3) . . . . ?
C2 C18 C23 C22 179.31(18) . . . . ?
C2 N3 C24 C29 -78.3(2) . . . . ?
C4 N3 C24 C29 107.75(18) . . . . ?
C2 N3 C24 C25 96.80(18) . . . . ?
C4 N3 C24 C25 -77.1(2) . . . . ?
C29 C24 C25 C26 1.9(2) . . . . ?
N3 C24 C25 C26 -172.93(14) . . . . ?
C29 C24 C25 C30 -178.21(15) . . . . ?
N3 C24 C25 C30 6.9(2) . . . . ?
C24 C25 C26 C27 0.9(2) . . . . ?
C30 C25 C26 C27 -179.00(15) . . . . ?
C25 C26 C27 C28 -2.9(3) . . . . ?
C26 C27 C28 C29 2.1(3) . . . . ?
C25 C24 C29 C28 -2.6(2) . . . . ?
N3 C24 C29 C28 172.22(14) . . . . ?
C25 C24 C29 C33 176.82(15) . . . . ?
N3 C24 C29 C33 -8.3(2) . . . . ?
C27 C28 C29 C24 0.6(2) . . . . ?
C27 C28 C29 C33 -178.90(16) . . . . ?
C26 C25 C30 C32 -60.7(2) . . . . ?
C24 C25 C30 C32 119.45(17) . . . . ?
C26 C25 C30 C31 61.9(2) . . . . ?
C24 C25 C30 C31 -118.00(17) . . . . ?
C24 C29 C33 C35 -121.46(17) . . . . ?
C28 C29 C33 C35 58.0(2) . . . . ?
C24 C29 C33 C34 116.33(18) . . . . ?
C28 C29 C33 C34 -64.2(2) . . . . ?
C5 C4 C36 N43 91.1(2) . . . . ?
N3 C4 C36 N43 -86.36(18) . . . . ?
C5 C4 C36 C37 -35.9(2) . . . . ?
N3 C4 C36 C37 146.68(14) . . . . ?
N43 C36 C37 C42 1.5(2) . . . . ?
C4 C36 C37 C42 130.41(16) . . . . ?
N43 C36 C37 C38 179.43(14) . . . . ?
C4 C36 C37 C38 -51.6(2) . . . . ?
C42 C37 C38 C39 -1.0(3) . . . . ?
C36 C37 C38 C39 -178.97(15) . . . . ?
C37 C38 C39 C40 0.2(3) . . . . ?
C38 C39 C40 C41 0.6(3) . . . . ?
C39 C40 C41 C42 -0.7(3) . . . . ?
C40 C41 C42 C37 -0.1(3) . . . . ?
C38 C37 C42 C41 0.9(3) . . . . ?
C36 C37 C42 C41 178.93(16) . . . . ?
C4 C36 N43 N44 -7.41(19) . . . . ?
C37 C36 N43 N44 120.47(14) . . . . ?
C36 N43 N44 C45 -174.92(14) . . . . ?
N43 N44 C45 C52 -173.96(14) . . . . ?
N43 N44 C45 C46 2.2(2) . . . . ?
N44 C45 C46 C47 146.99(17) . . . . ?
C52 C45 C46 C47 -37.0(2) . . . . ?
N44 C45 C46 C51 -32.8(3) . . . . ?
C52 C45 C46 C51 143.18(17) . . . . ?
C51 C46 C47 C48 -1.1(3) . . . . ?
C45 C46 C47 C48 179.08(17) . . . . ?
C46 C47 C48 C49 -0.1(3) . . . . ?
C47 C48 C49 C50 1.1(3) . . . . ?
C48 C49 C50 C51 -0.9(3) . . . . ?
C49 C50 C51 C46 -0.3(3) . . . . ?
C47 C46 C51 C50 1.3(3) . . . . ?
C45 C46 C51 C50 -178.91(16) . . . . ?
N44 C45 C52 O53 174.08(17) . . . . ?
C46 C45 C52 O53 -2.4(3) . . . . ?
N44 C45 C52 O54 -3.7(2) . . . . ?
C46 C45 C52 O54 179.89(14) . . . . ?
O53 C52 O54 C55 -5.0(2) . . . . ?
C45 C52 O54 C55 172.90(16) . . . . ?
C4 C5 C56 C57 123.2(2) . . . . ?
N1 C5 C56 C57 -61.8(2) . . . . ?
C4 C5 C56 C61 -56.3(2) . . . . ?
N1 C5 C56 C61 118.73(18) . . . . ?
C61 C56 C57 C58 0.5(3) . . . . ?
C5 C56 C57 C58 -178.93(16) . . . . ?
C56 C57 C58 C59 -0.9(3) . . . . ?
C57 C58 C59 C60 0.7(3) . . . . ?
C58 C59 C60 C61 -0.1(3) . . . . ?
C57 C56 C61 C60 0.1(3) . . . . ?
C5 C56 C61 C60 179.54(15) . . . . ?
C59 C60 C61 C56 -0.3(3) . . . . ?
C66 N62 C63 N64 -0.92(18) . . . . ?
C67 N62 C63 N64 165.64(15) . . . . ?
C66 N62 C63 C79 176.24(16) . . . . ?
C67 N62 C63 C79 -17.2(3) . . . . ?
N62 C63 N64 C65 0.55(18) . . . . ?
C79 C63 N64 C65 -176.58(15) . . . . ?
N62 C63 N64 C85 -175.86(14) . . . . ?
C79 C63 N64 C85 7.0(3) . . . . ?
C63 N64 C65 C66 0.03(18) . . . . ?
C85 N64 C65 C66 176.35(14) . . . . ?
C63 N64 C65 C97 179.82(14) . . . . ?
C85 N64 C65 C97 -3.9(2) . . . . ?
N64 C65 C66 N62 -0.58(18) . . . . ?
C97 C65 C66 N62 179.67(16) . . . . ?
N64 C65 C66 C117 177.27(17) . . . . ?
C97 C65 C66 C117 -2.5(3) . . . . ?
C63 N62 C66 C65 0.95(19) . . . . ?
C67 N62 C66 C65 -165.87(15) . . . . ?
C63 N62 C66 C117 -177.08(16) . . . . ?
C67 N62 C66 C117 16.1(3) . . . . ?
C63 N62 C67 C72 -70.0(2) . . . . ?
C66 N62 C67 C72 94.7(2) . . . . ?
C63 N62 C67 C68 113.3(2) . . . . ?
C66 N62 C67 C68 -82.0(2) . . . . ?
C72 C67 C68 C69 -2.0(3) . . . . ?
N62 C67 C68 C69 174.39(16) . . . . ?
C72 C67 C68 C73 178.05(17) . . . . ?
N62 C67 C68 C73 -5.5(3) . . . . ?
C67 C68 C69 C70 1.8(3) . . . . ?
C73 C68 C69 C70 -178.33(19) . . . . ?
C68 C69 C70 C71 -0.1(3) . . . . ?
C69 C70 C71 C72 -1.5(3) . . . . ?
C68 C67 C72 C71 0.6(3) . . . . ?
N62 C67 C72 C71 -175.90(16) . . . . ?
C68 C67 C72 C76 -179.12(18) . . . . ?
N62 C67 C72 C76 4.4(3) . . . . ?
C70 C71 C72 C67 1.2(3) . . . . ?
C70 C71 C72 C76 -179.08(19) . . . . ?
C69 C68 C73 C75 -63.1(2) . . . . ?
C67 C68 C73 C75 116.8(2) . . . . ?
C69 C68 C73 C74 57.9(2) . . . . ?
C67 C68 C73 C74 -122.19(19) . . . . ?
C67 C72 C76 C77 117.0(2) . . . . ?
C71 C72 C76 C77 -62.7(2) . . . . ?
C67 C72 C76 C78 -119.0(2) . . . . ?
C71 C72 C76 C78 61.2(3) . . . . ?
N62 C63 C79 C80 -36.0(3) . . . . ?
N64 C63 C79 C80 140.57(18) . . . . ?
N62 C63 C79 C84 145.89(17) . . . . ?
N64 C63 C79 C84 -37.5(3) . . . . ?
C84 C79 C80 C81 -0.4(3) . . . . ?
C63 C79 C80 C81 -178.49(17) . . . . ?
C79 C80 C81 C82 1.0(3) . . . . ?
C80 C81 C82 C83 -1.0(3) . . . . ?
C81 C82 C83 C84 0.3(3) . . . . ?
C82 C83 C84 C79 0.3(3) . . . . ?
C80 C79 C84 C83 -0.3(3) . . . . ?
C63 C79 C84 C83 177.81(16) . . . . ?
C63 N64 C85 C86 -79.8(2) . . . . ?
C65 N64 C85 C86 104.33(18) . . . . ?
C63 N64 C85 C90 94.68(19) . . . . ?
C65 N64 C85 C90 -81.14(19) . . . . ?
C90 C85 C86 C87 -2.3(2) . . . . ?
N64 C85 C86 C87 171.92(14) . . . . ?
C90 C85 C86 C91 178.81(15) . . . . ?
N64 C85 C86 C91 -7.0(2) . . . . ?
C85 C86 C87 C88 0.3(2) . . . . ?
C91 C86 C87 C88 179.26(15) . . . . ?
C86 C87 C88 C89 1.8(3) . . . . ?
C87 C88 C89 C90 -2.1(3) . . . . ?
C88 C89 C90 C85 0.2(2) . . . . ?
C88 C89 C90 C94 -178.56(15) . . . . ?
C86 C85 C90 C89 2.0(2) . . . . ?
N64 C85 C90 C89 -172.23(13) . . . . ?
C86 C85 C90 C94 -179.23(15) . . . . ?
N64 C85 C90 C94 6.5(2) . . . . ?
C87 C86 C91 C93 57.1(2) . . . . ?
C85 C86 C91 C93 -124.05(18) . . . . ?
C87 C86 C91 C92 -65.0(2) . . . . ?
C85 C86 C91 C92 113.81(18) . . . . ?
C89 C90 C94 C96 -61.0(2) . . . . ?
C85 C90 C94 C96 120.28(17) . . . . ?
C89 C90 C94 C95 61.7(2) . . . . ?
C85 C90 C94 C95 -117.00(18) . . . . ?
C66 C65 C97 N104 94.3(2) . . . . ?
N64 C65 C97 N104 -85.46(19) . . . . ?
C66 C65 C97 C98 -33.8(3) . . . . ?
N64 C65 C97 C98 146.46(14) . . . . ?
N104 C97 C98 C99 179.48(15) . . . . ?
C65 C97 C98 C99 -50.1(2) . . . . ?
N104 C97 C98 C103 1.8(2) . . . . ?
C65 C97 C98 C103 132.23(16) . . . . ?
C103 C98 C99 C100 -1.5(3) . . . . ?
C97 C98 C99 C100 -179.16(17) . . . . ?
C98 C99 C100 C101 1.3(3) . . . . ?
C99 C100 C101 C102 -0.5(3) . . . . ?
C100 C101 C102 C103 -0.1(3) . . . . ?
C101 C102 C103 C98 -0.1(3) . . . . ?
C99 C98 C103 C102 0.8(3) . . . . ?
C97 C98 C103 C102 178.57(16) . . . . ?
C65 C97 N104 N105 -15.63(19) . . . . ?
C98 C97 N104 N105 113.09(15) . . . . ?
C97 N104 N105 C106 -172.40(14) . . . . ?
N104 N105 C106 C113 -173.53(15) . . . . ?
N104 N105 C106 C107 5.0(3) . . . . ?
N105 C106 C107 C112 -31.8(3) . . . . ?
C113 C106 C107 C112 146.73(18) . . . . ?
N105 C106 C107 C108 148.11(18) . . . . ?
C113 C106 C107 C108 -33.4(3) . . . . ?
C112 C107 C108 C109 -1.4(3) . . . . ?
C106 C107 C108 C109 178.68(17) . . . . ?
C107 C108 C109 C110 0.4(3) . . . . ?
C108 C109 C110 C111 0.6(3) . . . . ?
C109 C110 C111 C112 -0.5(3) . . . . ?
C110 C111 C112 C107 -0.5(3) . . . . ?
C108 C107 C112 C111 1.5(3) . . . . ?
C106 C107 C112 C111 -178.62(18) . . . . ?
N105 C106 C113 O114 176.42(18) . . . . ?
C107 C106 C113 O114 -2.3(3) . . . . ?
N105 C106 C113 O115 -0.9(2) . . . . ?
C107 C106 C113 O115 -179.62(15) . . . . ?
O114 C113 O115 C116 -4.7(3) . . . . ?
C106 C113 O115 C116 172.88(17) . . . . ?
C65 C66 C117 C122 -50.2(3) . . . . ?
N62 C66 C117 C122 127.33(19) . . . . ?
C65 C66 C117 C118 127.3(2) . . . . ?
N62 C66 C117 C118 -55.1(3) . . . . ?
C122 C117 C118 C119 0.7(3) . . . . ?
C66 C117 C118 C119 -176.86(19) . . . . ?
C117 C118 C119 C120 -0.8(3) . . . . ?
C118 C119 C120 C121 0.9(4) . . . . ?
C119 C120 C121 C122 -0.8(4) . . . . ?
C118 C117 C122 C121 -0.6(3) . . . . ?
C66 C117 C122 C121 177.04(19) . . . . ?
C120 C121 C122 C117 0.7(4) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040


