# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1540162'
_audit_update_record             
;
2017-03-25 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H30 N2 O3'
_chemical_formula_weight         550.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   9.4914(7)
_cell_length_b                   13.1578(9)
_cell_length_c                   24.0997(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.676(2)
_cell_angle_gamma                90.00
_cell_volume                     3009.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6145
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            37829
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         27.49
_reflns_number_total             6865
_reflns_number_gt                4815
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0787P)²+0.0993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6865
_refine_ls_number_parameters     381
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70502(10) 0.74783(7) 0.18210(4) 0.0521(2) Uani 1 1 d . . .
O2 O 0.59559(11) 1.00226(9) 0.34243(4) 0.0653(3) Uani 1 1 d . . .
O3 O 0.64577(12) 0.76775(9) 0.36112(4) 0.0736(3) Uani 1 1 d . . .
N1 N 0.86257(11) 0.85598(8) 0.13918(4) 0.0428(2) Uani 1 1 d . . .
N2 N 0.92436(11) 0.95163(8) 0.14984(5) 0.0442(3) Uani 1 1 d . . .
C1 C 0.77558(13) 0.82483(9) 0.18097(5) 0.0403(3) Uani 1 1 d . . .
C2 C 0.79291(12) 0.90439(9) 0.22671(5) 0.0386(3) Uani 1 1 d . . .
C3 C 0.86283(13) 0.85148(9) 0.27922(5) 0.0406(3) Uani 1 1 d . . .
H3 H 0.8112 0.7862 0.2851 0.049 Uiso 1 1 calc R . .
C4 C 0.82345(13) 0.92250(10) 0.32774(5) 0.0420(3) Uani 1 1 d . . .
H4 H 0.8903 0.9812 0.3271 0.050 Uiso 1 1 calc R . .
C5 C 0.67935(14) 0.96283(10) 0.31124(5) 0.0463(3) Uani 1 1 d . . .
C6 C 0.65939(13) 0.95060(9) 0.25016(5) 0.0422(3) Uani 1 1 d . . .
C7 C 0.53541(14) 0.97742(10) 0.22717(6) 0.0478(3) Uani 1 1 d . . .
H7 H 0.4712 1.0056 0.2529 0.057 Uiso 1 1 calc R . .
C8 C 0.47947(13) 0.97196(10) 0.17067(5) 0.0473(3) Uani 1 1 d . . .
C9 C 0.33366(15) 0.96600(13) 0.16320(6) 0.0615(4) Uani 1 1 d . . .
H9 H 0.2743 0.9697 0.1946 0.074 Uiso 1 1 calc R . .
C10 C 0.27431(16) 0.95485(15) 0.11122(7) 0.0718(5) Uani 1 1 d . . .
H10 H 0.1749 0.9501 0.1071 0.086 Uiso 1 1 calc R . .
C11 C 0.35764(18) 0.95052(14) 0.06553(7) 0.0698(5) Uani 1 1 d . . .
H11 H 0.3167 0.9417 0.0297 0.084 Uiso 1 1 calc R . .
C12 C 0.50146(17) 0.95899(14) 0.07178(6) 0.0695(5) Uani 1 1 d . . .
H12 H 0.5597 0.9568 0.0400 0.083 Uiso 1 1 calc R . .
C13 C 0.56152(15) 0.97058(12) 0.12355(6) 0.0585(4) Uani 1 1 d . . .
H13 H 0.6608 0.9778 0.1271 0.070 Uiso 1 1 calc R . .
C14 C 0.87834(12) 0.81295(10) 0.08566(5) 0.0443(3) Uani 1 1 d . . .
C15 C 0.88235(14) 0.70872(11) 0.07937(6) 0.0506(3) Uani 1 1 d . . .
H15 H 0.8760 0.6654 0.1108 0.061 Uiso 1 1 calc R . .
C16 C 0.89573(16) 0.66813(13) 0.02666(7) 0.0641(4) Uani 1 1 d . . .
H16 H 0.8979 0.5965 0.0220 0.077 Uiso 1 1 calc R . .
C17 C 0.90592(19) 0.73024(17) -0.01894(7) 0.0780(5) Uani 1 1 d . . .
H17 H 0.9145 0.7016 -0.0549 0.094 Uiso 1 1 calc R . .
C18 C 0.9036(2) 0.83410(17) -0.01225(7) 0.0796(5) Uani 1 1 d . . .
H18 H 0.9117 0.8771 -0.0437 0.096 Uiso 1 1 calc R . .
C19 C 0.88960(17) 0.87626(13) 0.03978(6) 0.0620(4) Uani 1 1 d . . .
H19 H 0.8877 0.9480 0.0442 0.074 Uiso 1 1 calc R . .
C20 C 0.88791(12) 0.97965(9) 0.19847(5) 0.0403(3) Uani 1 1 d . . .
C21 C 0.93927(16) 1.07783(10) 0.22200(6) 0.0551(4) Uani 1 1 d . . .
H21A H 0.9825 1.1183 0.1926 0.083 Uiso 1 1 calc R . .
H21B H 1.0092 1.0644 0.2513 0.083 Uiso 1 1 calc R . .
H21C H 0.8598 1.1154 0.2376 0.083 Uiso 1 1 calc R . .
C22 C 1.01713(14) 0.82475(10) 0.27358(5) 0.0465(3) Uani 1 1 d . . .
C23 C 1.05538(17) 0.74222(12) 0.24089(7) 0.0622(4) Uani 1 1 d . . .
H23 H 0.9846 0.7032 0.2225 0.075 Uiso 1 1 calc R . .
C24 C 1.1968(2) 0.71650(14) 0.23492(9) 0.0829(6) Uani 1 1 d . . .
H24 H 1.2221 0.6614 0.2116 0.099 Uiso 1 1 calc R . .
C25 C 1.3000(2) 0.77028(15) 0.26254(10) 0.0843(6) Uani 1 1 d . . .
H25 H 1.3963 0.7526 0.2581 0.101 Uiso 1 1 calc R . .
C26 C 1.26377(17) 0.84916(15) 0.29633(8) 0.0721(5) Uani 1 1 d . . .
H26 H 1.3348 0.8846 0.3166 0.086 Uiso 1 1 calc R . .
C27 C 1.12391(14) 0.87775(13) 0.30117(6) 0.0563(4) Uani 1 1 d . . .
H27 H 1.1005 0.9344 0.3237 0.068 Uiso 1 1 calc R . .
C28 C 0.83396(14) 0.87565(10) 0.38450(5) 0.0463(3) Uani 1 1 d . . .
C29 C 0.74157(17) 0.78522(11) 0.39351(6) 0.0562(4) Uani 1 1 d . . .
C30 C 0.7691(2) 0.71569(14) 0.44185(8) 0.0806(5) Uani 1 1 d . . .
H30A H 0.7514 0.7522 0.4765 0.121 Uiso 1 1 calc R . .
H30B H 0.8673 0.6929 0.4413 0.121 Uiso 1 1 calc R . .
H30C H 0.7064 0.6566 0.4392 0.121 Uiso 1 1 calc R . .
C31 C 0.91879(15) 0.91016(11) 0.42519(5) 0.0513(3) Uani 1 1 d . . .
H31 H 0.9168 0.8738 0.4592 0.062 Uiso 1 1 calc R . .
C32 C 1.01464(14) 0.99800(10) 0.42308(5) 0.0477(3) Uani 1 1 d . . .
C33 C 0.97467(15) 1.09327(11) 0.40397(6) 0.0550(4) Uani 1 1 d . . .
H33 H 0.8792 1.1053 0.3937 0.066 Uiso 1 1 calc R . .
C34 C 1.07165(18) 1.17051(12) 0.39962(7) 0.0656(4) Uani 1 1 d . . .
H34 H 1.0427 1.2355 0.3866 0.079 Uiso 1 1 calc R . .
C35 C 1.21009(19) 1.15403(14) 0.41408(7) 0.0717(5) Uani 1 1 d . . .
H35 H 1.2773 1.2070 0.4103 0.086 Uiso 1 1 calc R . .
C36 C 1.25109(18) 1.06102(15) 0.43403(8) 0.0776(5) Uani 1 1 d . . .
H36 H 1.3468 1.0496 0.4441 0.093 Uiso 1 1 calc R . .
C37 C 1.15378(16) 0.98401(13) 0.43947(7) 0.0651(4) Uani 1 1 d . . .
H37 H 1.1824 0.9205 0.4546 0.078 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2149(14) . ?
O2 C5 1.2167(16) . ?
O3 C29 1.2134(17) . ?
N1 C1 1.3725(16) . ?
N1 N2 1.4108(14) . ?
N1 C14 1.4181(16) . ?
N2 C20 1.2800(16) . ?
C1 C2 1.5276(16) . ?
C2 C20 1.5072(17) . ?
C2 C6 1.5205(17) . ?
C2 C3 1.5831(16) . ?
C3 C22 1.5138(18) . ?
C3 C4 1.5463(17) . ?
C3 H3 1.0000 . ?
C4 C28 1.5024(18) . ?
C4 C5 1.5158(18) . ?
C4 H4 1.0000 . ?
C5 C6 1.4906(18) . ?
C6 C7 1.3418(17) . ?
C7 C8 1.4575(18) . ?
C7 H7 0.9500 . ?
C8 C13 1.385(2) . ?
C8 C9 1.3957(19) . ?
C9 C10 1.375(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.364(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.3804(19) . ?
C14 C19 1.389(2) . ?
C15 C16 1.385(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.4905(17) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.392(2) . ?
C22 C27 1.393(2) . ?
C23 C24 1.394(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.366(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C31 1.3408(18) . ?
C28 C29 1.4955(19) . ?
C29 C30 1.502(2) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.4722(19) . ?
C31 H31 0.9500 . ?
C32 C37 1.3862(19) . ?
C32 C33 1.387(2) . ?
C33 C34 1.376(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.373(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.370(2) . ?
C35 H35 0.9500 . ?
C36 C37 1.378(2) . ?
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
C1 N1 N2 112.65(10) . . ?
C1 N1 C14 128.25(10) . . ?
N2 N1 C14 118.27(10) . . ?
C20 N2 N1 107.90(10) . . ?
O1 C1 N1 127.01(11) . . ?
O1 C1 C2 127.58(11) . . ?
N1 C1 C2 105.33(10) . . ?
C20 C2 C6 114.25(10) . . ?
C20 C2 C1 100.61(10) . . ?
C6 C2 C1 117.33(10) . . ?
C20 C2 C3 113.74(9) . . ?
C6 C2 C3 102.84(9) . . ?
C1 C2 C3 108.42(9) . . ?
C22 C3 C4 116.81(10) . . ?
C22 C3 C2 115.30(10) . . ?
C4 C3 C2 103.65(9) . . ?
C22 C3 H3 106.8 . . ?
C4 C3 H3 106.8 . . ?
C2 C3 H3 106.8 . . ?
C28 C4 C5 115.63(11) . . ?
C28 C4 C3 115.25(10) . . ?
C5 C4 C3 103.80(9) . . ?
C28 C4 H4 107.2 . . ?
C5 C4 H4 107.2 . . ?
C3 C4 H4 107.2 . . ?
O2 C5 C6 125.43(12) . . ?
O2 C5 C4 125.54(12) . . ?
C6 C5 C4 108.98(11) . . ?
C7 C6 C5 118.68(12) . . ?
C7 C6 C2 133.03(12) . . ?
C5 C6 C2 108.26(10) . . ?
C6 C7 C8 132.90(13) . . ?
C6 C7 H7 113.5 . . ?
C8 C7 H7 113.5 . . ?
C13 C8 C9 117.38(12) . . ?
C13 C8 C7 124.38(12) . . ?
C9 C8 C7 118.24(12) . . ?
C10 C9 C8 121.22(14) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 120.30(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.46(15) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 120.59(15) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 120.99(14) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C15 C14 C19 120.38(12) . . ?
C15 C14 N1 119.99(11) . . ?
C19 C14 N1 119.63(13) . . ?
C14 C15 C16 119.13(14) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.81(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.71(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.52(16) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 119.45(16) . . ?
C18 C19 H19 120.3 . . ?
C14 C19 H19 120.3 . . ?
N2 C20 C21 120.49(11) . . ?
N2 C20 C2 113.20(10) . . ?
C21 C20 C2 126.32(11) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 117.88(14) . . ?
C23 C22 C3 119.40(13) . . ?
C27 C22 C3 122.69(12) . . ?
C22 C23 C24 120.38(17) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.47(18) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.80(17) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.31(18) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 121.08(16) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C31 C28 C29 120.74(12) . . ?
C31 C28 C4 124.05(12) . . ?
C29 C28 C4 115.21(11) . . ?
O3 C29 C28 119.57(13) . . ?
O3 C29 C30 120.38(14) . . ?
C28 C29 C30 120.04(13) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 C32 127.34(12) . . ?
C28 C31 H31 116.3 . . ?
C32 C31 H31 116.3 . . ?
C37 C32 C33 118.07(13) . . ?
C37 C32 C31 118.23(13) . . ?
C33 C32 C31 123.67(12) . . ?
C34 C33 C32 120.81(14) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C35 C34 C33 120.22(15) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C36 C35 C34 119.82(15) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C35 C36 C37 120.16(15) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C36 C37 C32 120.83(15) . . ?
C36 C37 H37 119.6 . . ?
C32 C37 H37 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
C1 N1 N2 C20 4.36(14) . . . . ?
C14 N1 N2 C20 174.80(10) . . . . ?
N2 N1 C1 O1 177.21(12) . . . . ?
C14 N1 C1 O1 7.9(2) . . . . ?
N2 N1 C1 C2 -5.80(13) . . . . ?
C14 N1 C1 C2 -175.07(11) . . . . ?
O1 C1 C2 C20 -178.25(12) . . . . ?
N1 C1 C2 C20 4.79(11) . . . . ?
O1 C1 C2 C6 -53.69(17) . . . . ?
N1 C1 C2 C6 129.35(11) . . . . ?
O1 C1 C2 C3 62.14(16) . . . . ?
N1 C1 C2 C3 -114.82(10) . . . . ?
C20 C2 C3 C22 -38.86(14) . . . . ?
C6 C2 C3 C22 -162.95(10) . . . . ?
C1 C2 C3 C22 72.15(13) . . . . ?
C20 C2 C3 C4 90.05(12) . . . . ?
C6 C2 C3 C4 -34.04(11) . . . . ?
C1 C2 C3 C4 -158.94(10) . . . . ?
C22 C3 C4 C28 -71.21(14) . . . . ?
C2 C3 C4 C28 160.80(10) . . . . ?
C22 C3 C4 C5 161.32(10) . . . . ?
C2 C3 C4 C5 33.34(12) . . . . ?
C28 C4 C5 O2 34.85(18) . . . . ?
C3 C4 C5 O2 162.08(13) . . . . ?
C28 C4 C5 C6 -147.66(11) . . . . ?
C3 C4 C5 C6 -20.43(13) . . . . ?
O2 C5 C6 C7 -5.5(2) . . . . ?
C4 C5 C6 C7 176.97(12) . . . . ?
O2 C5 C6 C2 176.12(13) . . . . ?
C4 C5 C6 C2 -1.37(14) . . . . ?
C20 C2 C6 C7 80.22(17) . . . . ?
C1 C2 C6 C7 -37.2(2) . . . . ?
C3 C2 C6 C7 -156.03(14) . . . . ?
C20 C2 C6 C5 -101.77(12) . . . . ?
C1 C2 C6 C5 140.83(11) . . . . ?
C3 C2 C6 C5 21.97(12) . . . . ?
C5 C6 C7 C8 -177.21(14) . . . . ?
C2 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C13 -24.9(2) . . . . ?
C6 C7 C8 C9 153.95(16) . . . . ?
C13 C8 C9 C10 2.7(2) . . . . ?
C7 C8 C9 C10 -176.27(15) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C12 C13 C8 1.3(3) . . . . ?
C9 C8 C13 C12 -3.0(2) . . . . ?
C7 C8 C13 C12 175.93(15) . . . . ?
C1 N1 C14 C15 -41.69(18) . . . . ?
N2 N1 C14 C15 149.56(11) . . . . ?
C1 N1 C14 C19 138.28(14) . . . . ?
N2 N1 C14 C19 -30.47(17) . . . . ?
C19 C14 C15 C16 -0.91(19) . . . . ?
N1 C14 C15 C16 179.06(12) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -0.7(3) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 C18 0.6(2) . . . . ?
N1 C14 C19 C18 -179.40(14) . . . . ?
N1 N2 C20 C21 178.96(11) . . . . ?
N1 N2 C20 C2 -0.78(13) . . . . ?
C6 C2 C20 N2 -129.15(11) . . . . ?
C1 C2 C20 N2 -2.51(13) . . . . ?
C3 C2 C20 N2 113.18(12) . . . . ?
C6 C2 C20 C21 51.13(16) . . . . ?
C1 C2 C20 C21 177.76(12) . . . . ?
C3 C2 C20 C21 -66.54(16) . . . . ?
C4 C3 C22 C23 163.34(12) . . . . ?
C2 C3 C22 C23 -74.57(15) . . . . ?
C4 C3 C22 C27 -14.79(17) . . . . ?
C2 C3 C22 C27 107.30(13) . . . . ?
C27 C22 C23 C24 -2.1(2) . . . . ?
C3 C22 C23 C24 179.72(13) . . . . ?
C22 C23 C24 C25 2.0(3) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C27 -2.6(3) . . . . ?
C25 C26 C27 C22 2.5(2) . . . . ?
C23 C22 C27 C26 -0.1(2) . . . . ?
C3 C22 C27 C26 178.03(13) . . . . ?
C5 C4 C28 C31 -119.11(15) . . . . ?
C3 C4 C28 C31 119.64(15) . . . . ?
C5 C4 C28 C29 60.93(15) . . . . ?
C3 C4 C28 C29 -60.32(15) . . . . ?
C31 C28 C29 O3 164.84(14) . . . . ?
C4 C28 C29 O3 -15.2(2) . . . . ?
C31 C28 C29 C30 -16.2(2) . . . . ?
C4 C28 C29 C30 163.76(14) . . . . ?
C29 C28 C31 C32 -179.53(14) . . . . ?
C4 C28 C31 C32 0.5(2) . . . . ?
C28 C31 C32 C37 -128.75(16) . . . . ?
C28 C31 C32 C33 49.2(2) . . . . ?
C37 C32 C33 C34 2.2(2) . . . . ?
C31 C32 C33 C34 -175.69(14) . . . . ?
C32 C33 C34 C35 0.2(2) . . . . ?
C33 C34 C35 C36 -1.4(3) . . . . ?
C34 C35 C36 C37 0.2(3) . . . . ?
C35 C36 C37 C32 2.3(3) . . . . ?
C33 C32 C37 C36 -3.5(2) . . . . ?
C31 C32 C37 C36 174.54(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_p20170518a
_database_code_depnum_ccdc_archive 'CCDC 1567473'
_audit_update_record             
;
2017-08-08 deposited with the CCDC.
2018-11-27 downloaded from the CCDC.
;
_audit_creation_date             2017-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H24 N2 O2'
_chemical_formula_sum            'C31 H24 N2 O2'
_chemical_formula_weight         456.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         C41H32N2O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.50950(10)
_cell_length_b                   15.42510(10)
_cell_length_c                   22.00390(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.7770(10)
_cell_angle_gamma                90
_cell_volume                     4689.56(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28791
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.0740
_cell_measurement_theta_min      3.2520
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.3a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0079
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            39753
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.248
_diffrn_reflns_theta_min         3.558
_diffrn_ambient_temperature      294.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00 -21.00   1.00    5.00    --  -35.00 -72.00-108.00  104
  2  ω   -124.00 -29.00   1.00    5.00    --  -35.00 -72.00-180.00   95
  3  ω    -50.00  40.00   1.00    5.00    --  -35.00  72.00-144.00   90
  4  ω   -125.00 -21.00   1.00    5.00    --  -35.00 -72.00 -72.00  104
  5  ω    -50.00  40.00   1.00    5.00    --  -35.00  72.00-180.00   90
  6  ω   -112.00 -21.00   1.00    5.00    --  -35.00 -15.00  36.00   91
  7  ω   -115.00 -25.00   1.00    5.00    --  -35.00 -44.00 -72.00   90
  8  ω   -115.00 -25.00   1.00    5.00    --  -35.00 -72.00 -36.00   90
  9  ω   -200.00 -96.00   1.00    5.00    -- -110.00 -72.00 -36.00  104
 10  ω   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00-144.00   91
 11  ω   -125.00 -31.00   1.00    5.00    -- -110.00  72.00-108.00   94
 12  ω   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00-108.00   91
 13  ω   -200.00 -96.00   1.00    5.00    -- -110.00 -44.00 -36.00  104
 14  ω   -124.00 -26.00   1.00    5.00    -- -110.00  43.00 -36.00   98
 15  ω   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00-144.00   91
 16  ω   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00 -72.00   91
 17  ω   -187.00 -96.00   1.00    5.00    -- -110.00 -44.00-180.00   91
 18  ω   -125.00 -27.00   1.00    5.00    -- -110.00  72.00  36.00   98
 19  ω   -115.00 -25.00   1.00    5.00    -- -110.00  72.00 -36.00   90
 20  ω   -198.00 -96.00   1.00    5.00    -- -110.00 -72.00 -72.00  102
 21  ω   -125.00 -33.00   1.00    5.00    -- -110.00  14.00   0.00   92
 22  ω   -187.00 -96.00   1.00    5.00    -- -110.00 -72.00-108.00   91
 23  ω   -191.00-101.00   1.00    5.00    -- -110.00 -15.00-180.00   90
 24  ω   -200.00-110.00   1.00    5.00    -- -110.00 -15.00 -72.00   90
 25  ω   -195.00-105.00   1.00    5.00    -- -110.00 -15.00-144.00   90
 26  ω   -125.00 -33.00   1.00    5.00    -- -110.00  72.00 -72.00   92
 27  ω   -187.00 -97.00   1.00    5.00    -- -110.00 -72.00-180.00   90
 28  ω   -187.00 -97.00   1.00    5.00    -- -110.00 -15.00-108.00   90
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1033241000
_diffrn_orient_matrix_UB_12      -0.0076684000
_diffrn_orient_matrix_UB_13      -0.0049716000
_diffrn_orient_matrix_UB_21      -0.0415848000
_diffrn_orient_matrix_UB_22      -0.0308690000
_diffrn_orient_matrix_UB_23      -0.0696251000
_diffrn_orient_matrix_UB_31      -0.0053012000
_diffrn_orient_matrix_UB_32      0.0946818000
_diffrn_orient_matrix_UB_33      -0.0230772000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4756
_reflns_number_total             5030
_reflns_odcompleteness_completeness 98.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     79.00
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.3a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00204(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+1.4190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1010
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C15(H15), C19(H19), C11(H11), C16(H16), C12(H12), C18(H18),
 C17(H17), C21(H21), C00R(H00R), C25(H25), C00T(H00T), C22(H22), C00V(H00V),
 C00W(H00W), C00X(H00X), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36073(5) 0.79963(5) 0.74293(3) 0.04897(19) Uani 1 1 d . . . . .
O2 O 0.22797(6) 0.64847(8) 0.58046(4) 0.0735(3) Uani 1 1 d . . . . .
N1 N 0.52664(6) 0.78361(6) 0.78551(4) 0.0475(2) Uani 1 1 d . . . . .
N2 N 0.60011(6) 0.73418(7) 0.77200(4) 0.0513(2) Uani 1 1 d . . . . .
C9 C 0.42772(7) 0.59759(6) 0.80211(5) 0.0413(2) Uani 1 1 d . . . . .
C8 C 0.40499(7) 0.60357(7) 0.73016(5) 0.0423(2) Uani 1 1 d . . . . .
H8 H 0.4320 0.5519 0.7160 0.051 Uiso 1 1 calc R . . . .
C14 C 0.50995(7) 0.54947(6) 0.83973(5) 0.0408(2) Uani 1 1 d . . . . .
C1 C 0.43656(7) 0.76406(7) 0.74543(5) 0.0415(2) Uani 1 1 d . . . . .
C7 C 0.29771(7) 0.60860(8) 0.69125(5) 0.0488(2) Uani 1 1 d . . . . .
H7A H 0.2691 0.5512 0.6844 0.059 Uiso 1 1 calc R . . . .
H7B H 0.2623 0.6438 0.7131 0.059 Uiso 1 1 calc R . . . .
C2 C 0.45079(7) 0.68654(7) 0.70635(5) 0.0416(2) Uani 1 1 d . . . . .
C13 C 0.53370(7) 0.55239(7) 0.90755(5) 0.0452(2) Uani 1 1 d . . . . .
C3 C 0.55974(7) 0.68202(7) 0.72639(5) 0.0461(2) Uani 1 1 d . . . . .
C10 C 0.37251(7) 0.64179(7) 0.83275(5) 0.0475(2) Uani 1 1 d . . . . .
H10 H 0.3180 0.6716 0.8085 0.057 Uiso 1 1 calc R . . . .
C5 C 0.39156(7) 0.69156(7) 0.63647(5) 0.0462(2) Uani 1 1 d . . . . .
C6 C 0.29604(8) 0.64945(8) 0.62891(5) 0.0507(3) Uani 1 1 d . . . . .
C15 C 0.56939(7) 0.49807(7) 0.81363(5) 0.0479(2) Uani 1 1 d . . . . .
H15 H 0.5541 0.4933 0.7695 0.057 Uiso 1 1 calc R . . . .
C19 C 0.41491(8) 0.71839(8) 0.58530(5) 0.0518(3) Uani 1 1 d . . . . .
H19 H 0.3670 0.7119 0.5463 0.062 Uiso 1 1 calc R . . . .
C00I C 0.55364(8) 0.84564(7) 0.83516(5) 0.0496(2) Uani 1 1 d . . . . .
C20 C 0.50583(9) 0.75669(8) 0.58229(5) 0.0523(3) Uani 1 1 d . . . . .
C11 C 0.39605(8) 0.64328(8) 0.89973(5) 0.0530(3) Uani 1 1 d . . . . .
H11 H 0.3573 0.6740 0.9190 0.064 Uiso 1 1 calc R . . . .
C16 C 0.64853(8) 0.45537(8) 0.85159(6) 0.0570(3) Uani 1 1 d . . . . .
H16 H 0.6869 0.4229 0.8331 0.068 Uiso 1 1 calc R . . . .
C12 C 0.47505(8) 0.60008(8) 0.93626(5) 0.0523(3) Uani 1 1 d . . . . .
H12 H 0.4906 0.6019 0.9805 0.063 Uiso 1 1 calc R . . . .
C18 C 0.61629(8) 0.50716(8) 0.94534(5) 0.0567(3) Uani 1 1 d . . . . .
H18 H 0.6324 0.5097 0.9896 0.068 Uiso 1 1 calc R . . . .
C4 C 0.61954(9) 0.62367(9) 0.69957(6) 0.0603(3) Uani 1 1 d . . . . .
H4A H 0.6280 0.6495 0.6619 0.090 Uiso 1 1 calc GR . . . .
H4B H 0.5875 0.5688 0.6888 0.090 Uiso 1 1 calc GR . . . .
H4C H 0.6816 0.6151 0.7307 0.090 Uiso 1 1 calc GR . . . .
C17 C 0.67226(9) 0.46022(9) 0.91813(6) 0.0617(3) Uani 1 1 d . . . . .
H17 H 0.7265 0.4312 0.9437 0.074 Uiso 1 1 calc R . . . .
C21 C 0.55356(10) 0.82168(8) 0.62314(6) 0.0601(3) Uani 1 1 d . . . . .
H21 H 0.5267 0.8445 0.6530 0.072 Uiso 1 1 calc R . . . .
C00R C 0.48539(10) 0.88153(9) 0.86032(6) 0.0631(3) Uani 1 1 d . . . . .
H00R H 0.4209 0.8648 0.8449 0.076 Uiso 1 1 calc R . . . .
C25 C 0.54634(11) 0.72544(10) 0.53655(7) 0.0688(4) Uani 1 1 d . . . . .
H25 H 0.5133 0.6841 0.5071 0.083 Uiso 1 1 calc R . . . .
C00T C 0.64997(9) 0.86945(10) 0.85994(6) 0.0654(3) Uani 1 1 d . . . . .
H00T H 0.6964 0.8448 0.8441 0.079 Uiso 1 1 calc R . . . .
C22 C 0.64149(11) 0.85282(11) 0.61967(8) 0.0767(4) Uani 1 1 d . . . . .
H22 H 0.6730 0.8971 0.6468 0.092 Uiso 1 1 calc R . . . .
C00V C 0.60953(13) 0.96742(10) 0.93258(7) 0.0796(4) Uani 1 1 d . . . . .
H00V H 0.6281 1.0089 0.9647 0.096 Uiso 1 1 calc R . . . .
C00W C 0.67660(12) 0.93011(11) 0.90843(7) 0.0801(4) Uani 1 1 d . . . . .
H00W H 0.7413 0.9459 0.9250 0.096 Uiso 1 1 calc R . . . .
C00X C 0.51422(13) 0.94254(10) 0.90862(7) 0.0758(4) Uani 1 1 d . . . . .
H00X H 0.4684 0.9671 0.9251 0.091 Uiso 1 1 calc R . . . .
C23 C 0.68241(12) 0.81842(13) 0.57610(10) 0.0887(5) Uani 1 1 d . . . . .
H23 H 0.7424 0.8381 0.5748 0.106 Uiso 1 1 calc R . . . .
C24 C 0.63445(13) 0.75515(12) 0.53465(9) 0.0860(5) Uani 1 1 d . . . . .
H24 H 0.6619 0.7323 0.5051 0.103 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2156(11) . ?
O2 C6 1.2122(13) . ?
N1 N2 1.4140(12) . ?
N1 C1 1.3687(13) . ?
N1 C00I 1.4146(15) . ?
N2 C3 1.2801(15) . ?
C9 C8 1.5181(13) . ?
C9 C14 1.4342(13) . ?
C9 C10 1.3751(14) . ?
C8 H8 0.9800 . ?
C8 C7 1.5324(13) . ?
C8 C2 1.6020(14) . ?
C14 C13 1.4260(14) . ?
C14 C15 1.4159(14) . ?
C1 C2 1.5233(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.5030(15) . ?
C2 C3 1.5076(13) . ?
C2 C5 1.5172(13) . ?
C13 C12 1.4116(15) . ?
C13 C18 1.4163(15) . ?
C3 C4 1.4913(15) . ?
C10 H10 0.9300 . ?
C10 C11 1.4078(15) . ?
C5 C6 1.4932(15) . ?
C5 C19 1.3366(15) . ?
C15 H15 0.9300 . ?
C15 C16 1.3655(15) . ?
C19 H19 0.9300 . ?
C19 C20 1.4653(16) . ?
C00I C00R 1.3888(17) . ?
C00I C00T 1.3857(16) . ?
C20 C21 1.3828(18) . ?
C20 C25 1.3974(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3569(16) . ?
C16 H16 0.9300 . ?
C16 C17 1.4001(17) . ?
C12 H12 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.3562(17) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.3870(19) . ?
C00R H00R 0.9300 . ?
C00R C00X 1.3851(19) . ?
C25 H25 0.9300 . ?
C25 C24 1.371(2) . ?
C00T H00T 0.9300 . ?
C00T C00W 1.383(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.379(2) . ?
C00V H00V 0.9300 . ?
C00V C00W 1.370(2) . ?
C00V C00X 1.376(2) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.372(3) . ?
C24 H24 0.9300 . ?

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 C00I 118.57(8) . . ?
C1 N1 N2 112.25(9) . . ?
C1 N1 C00I 129.16(9) . . ?
C3 N2 N1 108.05(8) . . ?
C14 C9 C8 120.73(8) . . ?
C10 C9 C8 120.50(9) . . ?
C10 C9 C14 118.69(9) . . ?
C9 C8 H8 107.5 . . ?
C9 C8 C7 116.48(8) . . ?
C9 C8 C2 114.20(8) . . ?
C7 C8 H8 107.5 . . ?
C7 C8 C2 103.23(8) . . ?
C2 C8 H8 107.5 . . ?
C13 C14 C9 118.71(9) . . ?
C15 C14 C9 123.92(9) . . ?
C15 C14 C13 117.37(9) . . ?
O1 C1 N1 127.08(10) . . ?
O1 C1 C2 127.27(9) . . ?
N1 C1 C2 105.63(8) . . ?
C8 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C6 C7 C8 105.17(8) . . ?
C6 C7 H7A 110.7 . . ?
C6 C7 H7B 110.7 . . ?
C1 C2 C8 107.53(7) . . ?
C3 C2 C8 111.71(8) . . ?
C3 C2 C1 100.48(8) . . ?
C3 C2 C5 121.18(8) . . ?
C5 C2 C8 102.07(8) . . ?
C5 C2 C1 113.55(8) . . ?
C12 C13 C14 119.92(9) . . ?
C12 C13 C18 120.77(10) . . ?
C18 C13 C14 119.32(10) . . ?
N2 C3 C2 112.84(9) . . ?
N2 C3 C4 120.49(10) . . ?
C4 C3 C2 126.65(10) . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 122.00(10) . . ?
C11 C10 H10 119.0 . . ?
C6 C5 C2 108.05(8) . . ?
C19 C5 C2 131.20(10) . . ?
C19 C5 C6 120.41(10) . . ?
O2 C6 C7 125.39(11) . . ?
O2 C6 C5 125.64(11) . . ?
C5 C6 C7 108.96(8) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.64(10) . . ?
C16 C15 H15 119.2 . . ?
C5 C19 H19 115.6 . . ?
C5 C19 C20 128.76(11) . . ?
C20 C19 H19 115.6 . . ?
C00R C00I N1 120.96(10) . . ?
C00T C00I N1 119.43(11) . . ?
C00T C00I C00R 119.59(12) . . ?
C21 C20 C19 122.82(10) . . ?
C21 C20 C25 118.75(12) . . ?
C25 C20 C19 118.42(12) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.21(10) . . ?
C12 C11 H11 119.9 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.42(11) . . ?
C17 C16 H16 119.8 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.42(10) . . ?
C11 C12 H12 119.8 . . ?
C13 C18 H18 119.4 . . ?
C17 C18 C13 121.14(11) . . ?
C17 C18 H18 119.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.07(10) . . ?
C18 C17 H17 120.0 . . ?
C20 C21 H21 119.9 . . ?
C20 C21 C22 120.11(13) . . ?
C22 C21 H21 119.9 . . ?
C00I C00R H00R 120.3 . . ?
C00X C00R C00I 119.45(13) . . ?
C00X C00R H00R 120.3 . . ?
C20 C25 H25 119.7 . . ?
C24 C25 C20 120.53(15) . . ?
C24 C25 H25 119.7 . . ?
C00I C00T H00T 120.2 . . ?
C00W C00T C00I 119.58(14) . . ?
C00W C00T H00T 120.2 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.25(16) . . ?
C23 C22 H22 119.9 . . ?
C00W C00V H00V 120.5 . . ?
C00W C00V C00X 118.96(14) . . ?
C00X C00V H00V 120.5 . . ?
C00T C00W H00W 119.4 . . ?
C00V C00W C00T 121.30(14) . . ?
C00V C00W H00W 119.4 . . ?
C00R C00X H00X 119.5 . . ?
C00V C00X C00R 121.09(15) . . ?
C00V C00X H00X 119.5 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.84(14) . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.41(14) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?

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
O1 C1 C2 C8 -69.39(12) . . . . ?
O1 C1 C2 C3 173.68(10) . . . . ?
O1 C1 C2 C5 42.76(14) . . . . ?
N1 N2 C3 C2 -3.87(12) . . . . ?
N1 N2 C3 C4 177.37(9) . . . . ?
N1 C1 C2 C8 108.67(8) . . . . ?
N1 C1 C2 C3 -8.27(10) . . . . ?
N1 C1 C2 C5 -139.19(9) . . . . ?
N1 C00I C00R C00X -179.57(12) . . . . ?
N1 C00I C00T C00W 179.94(12) . . . . ?
N2 N1 C1 O1 -174.97(9) . . . . ?
N2 N1 C1 C2 6.98(11) . . . . ?
N2 N1 C00I C00R -165.13(10) . . . . ?
N2 N1 C00I C00T 13.46(15) . . . . ?
C9 C8 C7 C6 157.54(9) . . . . ?
C9 C8 C2 C1 -42.55(10) . . . . ?
C9 C8 C2 C3 66.79(11) . . . . ?
C9 C8 C2 C5 -162.29(8) . . . . ?
C9 C14 C13 C12 1.75(14) . . . . ?
C9 C14 C13 C18 -178.24(10) . . . . ?
C9 C14 C15 C16 178.16(11) . . . . ?
C9 C10 C11 C12 -0.23(18) . . . . ?
C8 C9 C14 C13 174.15(9) . . . . ?
C8 C9 C14 C15 -6.37(15) . . . . ?
C8 C9 C10 C11 -174.86(10) . . . . ?
C8 C7 C6 O2 163.69(12) . . . . ?
C8 C7 C6 C5 -16.50(12) . . . . ?
C8 C2 C3 N2 -106.16(11) . . . . ?
C8 C2 C3 C4 72.51(13) . . . . ?
C8 C2 C5 C6 25.46(10) . . . . ?
C8 C2 C5 C19 -147.73(12) . . . . ?
C14 C9 C8 C7 146.96(10) . . . . ?
C14 C9 C8 C2 -92.76(11) . . . . ?
C14 C9 C10 C11 1.98(16) . . . . ?
C14 C13 C12 C11 -0.01(16) . . . . ?
C14 C13 C18 C17 -0.93(18) . . . . ?
C14 C15 C16 C17 1.08(19) . . . . ?
C1 N1 N2 C3 -2.20(12) . . . . ?
C1 N1 C00I C00R 16.62(17) . . . . ?
C1 N1 C00I C00T -164.79(11) . . . . ?
C1 C2 C3 N2 7.63(11) . . . . ?
C1 C2 C3 C4 -173.70(10) . . . . ?
C1 C2 C5 C6 -89.96(10) . . . . ?
C1 C2 C5 C19 96.84(14) . . . . ?
C7 C8 C2 C1 84.88(9) . . . . ?
C7 C8 C2 C3 -165.79(8) . . . . ?
C7 C8 C2 C5 -34.87(9) . . . . ?
C2 C8 C7 C6 31.56(11) . . . . ?
C2 C5 C6 O2 173.30(12) . . . . ?
C2 C5 C6 C7 -6.51(12) . . . . ?
C2 C5 C19 C20 -4.1(2) . . . . ?
C13 C14 C15 C16 -2.35(16) . . . . ?
C13 C18 C17 C16 -0.4(2) . . . . ?
C3 C2 C5 C6 150.32(10) . . . . ?
C3 C2 C5 C19 -22.88(18) . . . . ?
C10 C9 C8 C7 -36.26(14) . . . . ?
C10 C9 C8 C2 84.01(11) . . . . ?
C10 C9 C14 C13 -2.69(14) . . . . ?
C10 C9 C14 C15 176.80(10) . . . . ?
C10 C11 C12 C13 -0.78(18) . . . . ?
C5 C2 C3 N2 133.58(10) . . . . ?
C5 C2 C3 C4 -47.76(15) . . . . ?
C5 C19 C20 C21 -45.77(18) . . . . ?
C5 C19 C20 C25 133.56(14) . . . . ?
C6 C5 C19 C20 -176.57(11) . . . . ?
C15 C14 C13 C12 -177.77(10) . . . . ?
C15 C14 C13 C18 2.24(15) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C19 C5 C6 O2 -12.63(19) . . . . ?
C19 C5 C6 C7 167.56(10) . . . . ?
C19 C20 C21 C22 177.30(12) . . . . ?
C19 C20 C25 C24 -175.65(13) . . . . ?
C00I N1 N2 C3 179.27(9) . . . . ?
C00I N1 C1 O1 3.37(17) . . . . ?
C00I N1 C1 C2 -174.68(10) . . . . ?
C00I C00R C00X C00V -0.8(2) . . . . ?
C00I C00T C00W C00V 0.0(2) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C20 C25 C24 C23 -2.5(2) . . . . ?
C12 C13 C18 C17 179.08(12) . . . . ?
C18 C13 C12 C11 179.97(11) . . . . ?
C21 C20 C25 C24 3.7(2) . . . . ?
C21 C22 C23 C24 2.1(2) . . . . ?
C00R C00I C00T C00W -1.5(2) . . . . ?
C25 C20 C21 C22 -2.03(19) . . . . ?
C00T C00I C00R C00X 1.85(19) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C00W C00V C00X C00R -0.7(2) . . . . ?
C00X C00V C00W C00T 1.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.838
