# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2016

####################################################################### 
# 
# 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_ts134
_database_code_depnum_ccdc_archive 'CCDC 1037166'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 N O3'
_chemical_formula_sum            'C25 H23 N O3'
_chemical_formula_weight         385.44

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.3324(10)
_cell_length_b                   7.7981(5)
_cell_length_c                   15.3300(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.1780(10)
_cell_angle_gamma                90.00
_cell_volume                     1915.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2517
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      30.00

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9768
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14174
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.27
_diffrn_reflns_theta_max         30.01
_reflns_number_total             5579
_reflns_number_gt                3823
_reflns_threshold_expression     I>2u(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998)'

_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)+(0.0843P)²+0.0000P] 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         5579
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1573
_refine_ls_wR_factor_gt          0.1302
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17321(6) -0.11901(16) 0.34236(7) 0.0287(3) Uani 1 1 d . . .
O2 O 0.38892(6) -0.09917(14) 0.19491(7) 0.0248(3) Uani 1 1 d . . .
O3 O -0.32683(6) 0.65395(15) -0.27874(7) 0.0226(2) Uani 1 1 d . . .
N1 N 0.27942(7) -0.11793(16) 0.26610(8) 0.0184(3) Uani 1 1 d . . .
C1 C 0.50544(9) -0.2795(2) 0.46424(10) 0.0230(3) Uani 1 1 d . . .
H1A H 0.5380 -0.3324 0.5179 0.035 Uiso 1 1 calc R . .
H1B H 0.5409 -0.1998 0.4389 0.035 Uiso 1 1 calc R . .
H1C H 0.4847 -0.3689 0.4206 0.035 Uiso 1 1 calc R . .
C2 C 0.43175(8) -0.18213(19) 0.48809(9) 0.0184(3) Uani 1 1 d . . .
H2A H 0.3956 -0.2642 0.5123 0.022 Uiso 1 1 calc R . .
H2B H 0.4531 -0.0981 0.5355 0.022 Uiso 1 1 calc R . .
C3 C 0.37936(8) -0.08774(19) 0.40962(9) 0.0183(3) Uani 1 1 d . . .
H3A H 0.3387 -0.0130 0.4315 0.022 Uiso 1 1 calc R . .
H3B H 0.4162 -0.0136 0.3817 0.022 Uiso 1 1 calc R . .
C4 C 0.33258(9) -0.20996(19) 0.34001(10) 0.0195(3) Uani 1 1 d . . .
H4A H 0.3733 -0.2814 0.3162 0.023 Uiso 1 1 calc R . .
H4B H 0.2974 -0.2873 0.3684 0.023 Uiso 1 1 calc R . .
C5 C 0.19803(8) -0.0786(2) 0.27480(10) 0.0194(3) Uani 1 1 d . . .
C6 C 0.14531(8) 0.01215(19) 0.20014(9) 0.0175(3) Uani 1 1 d . . .
C7 C 0.17703(8) 0.06034(18) 0.12441(9) 0.0156(3) Uani 1 1 d . . .
C8 C 0.26085(8) 0.02137(18) 0.12026(9) 0.0160(3) Uani 1 1 d . . .
C9 C 0.31542(8) -0.06877(18) 0.19458(10) 0.0177(3) Uani 1 1 d . . .
C10 C 0.06357(9) 0.0506(2) 0.20414(10) 0.0223(3) Uani 1 1 d . . .
H10A H 0.0421 0.0178 0.2550 0.027 Uiso 1 1 calc R . .
C11 C 0.01210(9) 0.1367(2) 0.13459(10) 0.0237(3) Uani 1 1 d . . .
H11A H -0.0437 0.1622 0.1394 0.028 Uiso 1 1 calc R . .
C12 C 0.04040(8) 0.18622(19) 0.05841(9) 0.0178(3) Uani 1 1 d . . .
C13 C 0.12534(8) 0.14757(18) 0.05242(9) 0.0157(3) Uani 1 1 d . . .
C14 C 0.16116(9) 0.19172(19) -0.02174(10) 0.0188(3) Uani 1 1 d . . .
H14A H 0.1281 0.2499 -0.0706 0.023 Uiso 1 1 calc R . .
C15 C 0.24268(9) 0.1522(2) -0.02451(10) 0.0204(3) Uani 1 1 d . . .
H15A H 0.2651 0.1830 -0.0751 0.025 Uiso 1 1 calc R . .
C16 C 0.29285(8) 0.06673(19) 0.04678(10) 0.0186(3) Uani 1 1 d . . .
H16A H 0.3491 0.0400 0.0444 0.022 Uiso 1 1 calc R . .
C17 C -0.01487(9) 0.27697(19) -0.01391(10) 0.0208(3) Uani 1 1 d . . .
H17A H 0.0096 0.3257 -0.0596 0.025 Uiso 1 1 calc R . .
C18 C -0.09682(9) 0.29585(19) -0.02005(9) 0.0185(3) Uani 1 1 d . . .
H18A H -0.1202 0.2437 0.0255 0.022 Uiso 1 1 calc R . .
C19 C -0.15495(8) 0.38776(18) -0.08897(9) 0.0167(3) Uani 1 1 d . . .
C20 C -0.23636(8) 0.41295(19) -0.07616(10) 0.0185(3) Uani 1 1 d . . .
H20A H -0.2518 0.3688 -0.0239 0.022 Uiso 1 1 calc R . .
C21 C -0.29565(8) 0.50076(19) -0.13751(9) 0.0186(3) Uani 1 1 d . . .
H21A H -0.3507 0.5161 -0.1272 0.022 Uiso 1 1 calc R . .
C22 C -0.27344(8) 0.56554(18) -0.21389(9) 0.0173(3) Uani 1 1 d . . .
C23 C -0.19228(9) 0.5408(2) -0.22869(10) 0.0210(3) Uani 1 1 d . . .
H23A H -0.1771 0.5843 -0.2812 0.025 Uiso 1 1 calc R . .
C24 C -0.13437(9) 0.4533(2) -0.16715(10) 0.0207(3) Uani 1 1 d . . .
H24A H -0.0795 0.4373 -0.1779 0.025 Uiso 1 1 calc R . .
C25 C -0.41184(9) 0.6685(2) -0.26829(10) 0.0231(3) Uani 1 1 d . . .
H25A H -0.4449 0.7235 -0.3210 0.035 Uiso 1 1 calc R . .
H25B H -0.4144 0.7379 -0.2156 0.035 Uiso 1 1 calc R . .
H25C H -0.4343 0.5540 -0.2611 0.035 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 C5 1.2244(17) . ?
O2 C9 1.2228(16) . ?
O3 C22 1.3741(17) . ?
O3 C25 1.4326(17) . ?
N1 C9 1.3945(19) . ?
N1 C5 1.3956(17) . ?
N1 C4 1.4735(18) . ?
C1 C2 1.526(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5239(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5213(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.473(2) . ?
C6 C10 1.3811(18) . ?
C6 C7 1.4108(19) . ?
C7 C8 1.4156(18) . ?
C7 C13 1.4255(19) . ?
C8 C16 1.377(2) . ?
C8 C9 1.481(2) . ?
C10 C11 1.396(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.4399(18) . ?
C12 C17 1.469(2) . ?
C13 C14 1.4181(19) . ?
C14 C15 1.3753(19) . ?
C14 H14A 0.9500 . ?
C15 C16 1.401(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.3316(19) . ?
C17 H17A 0.9500 . ?
C18 C19 1.4637(19) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3951(18) . ?
C19 C24 1.403(2) . ?
C20 C21 1.3920(19) . ?
C20 H20A 0.9500 . ?
C21 C22 1.387(2) . ?
C21 H21A 0.9500 . ?
C22 C23 1.4007(19) . ?
C23 C24 1.380(2) . ?
C23 H23A 0.9500 . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O3 C25 116.85(11) . . ?
C9 N1 C5 124.69(12) . . ?
C9 N1 C4 117.59(11) . . ?
C5 N1 C4 117.63(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 113.54(12) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 112.33(12) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C3 112.03(12) . . ?
N1 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
O1 C5 N1 120.12(13) . . ?
O1 C5 C6 122.78(13) . . ?
N1 C5 C6 117.10(12) . . ?
C10 C6 C7 119.42(13) . . ?
C10 C6 C5 119.61(13) . . ?
C7 C6 C5 120.98(12) . . ?
C6 C7 C8 119.49(13) . . ?
C6 C7 C13 120.48(12) . . ?
C8 C7 C13 120.02(12) . . ?
C16 C8 C7 120.35(13) . . ?
C16 C8 C9 118.96(12) . . ?
C7 C8 C9 120.69(12) . . ?
O2 C9 N1 120.44(13) . . ?
O2 C9 C8 122.64(13) . . ?
N1 C9 C8 116.92(12) . . ?
C6 C10 C11 120.98(13) . . ?
C6 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C12 C11 C10 121.74(13) . . ?
C12 C11 H11A 119.1 . . ?
C10 C11 H11A 119.1 . . ?
C11 C12 C13 118.45(13) . . ?
C11 C12 C17 120.78(12) . . ?
C13 C12 C17 120.77(12) . . ?
C14 C13 C7 117.52(12) . . ?
C14 C13 C12 123.54(13) . . ?
C7 C13 C12 118.94(12) . . ?
C15 C14 C13 121.50(13) . . ?
C15 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
C14 C15 C16 120.39(13) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C8 C16 C15 120.21(13) . . ?
C8 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C18 C17 C12 124.68(14) . . ?
C18 C17 H17A 117.7 . . ?
C12 C17 H17A 117.7 . . ?
C17 C18 C19 127.42(14) . . ?
C17 C18 H18A 116.3 . . ?
C19 C18 H18A 116.3 . . ?
C20 C19 C24 117.50(13) . . ?
C20 C19 C18 118.03(13) . . ?
C24 C19 C18 124.47(12) . . ?
C21 C20 C19 122.09(13) . . ?
C21 C20 H20A 119.0 . . ?
C19 C20 H20A 119.0 . . ?
C22 C21 C20 119.22(13) . . ?
C22 C21 H21A 120.4 . . ?
C20 C21 H21A 120.4 . . ?
O3 C22 C21 124.09(12) . . ?
O3 C22 C23 116.08(12) . . ?
C21 C22 C23 119.82(13) . . ?
C24 C23 C22 120.14(13) . . ?
C24 C23 H23A 119.9 . . ?
C22 C23 H23A 119.9 . . ?
C23 C24 C19 121.23(13) . . ?
C23 C24 H24A 119.4 . . ?
C19 C24 H24A 119.4 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 67.87(16) . . . . ?
C9 N1 C4 C3 88.23(16) . . . . ?
C5 N1 C4 C3 -88.57(15) . . . . ?
C2 C3 C4 N1 177.69(11) . . . . ?
C9 N1 C5 O1 -175.92(14) . . . . ?
C4 N1 C5 O1 0.6(2) . . . . ?
C9 N1 C5 C6 3.9(2) . . . . ?
C4 N1 C5 C6 -179.50(12) . . . . ?
O1 C5 C6 C10 -1.7(2) . . . . ?
N1 C5 C6 C10 178.39(14) . . . . ?
O1 C5 C6 C7 178.34(15) . . . . ?
N1 C5 C6 C7 -1.5(2) . . . . ?
C10 C6 C7 C8 179.88(13) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C10 C6 C7 C13 -0.1(2) . . . . ?
C5 C6 C7 C13 179.77(13) . . . . ?
C6 C7 C8 C16 179.74(13) . . . . ?
C13 C7 C8 C16 -0.2(2) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C13 C7 C8 C9 179.84(13) . . . . ?
C5 N1 C9 O2 175.28(13) . . . . ?
C4 N1 C9 O2 -1.3(2) . . . . ?
C5 N1 C9 C8 -4.3(2) . . . . ?
C4 N1 C9 C8 179.14(12) . . . . ?
C16 C8 C9 O2 2.8(2) . . . . ?
C7 C8 C9 O2 -177.29(13) . . . . ?
C16 C8 C9 N1 -177.64(13) . . . . ?
C7 C8 C9 N1 2.3(2) . . . . ?
C7 C6 C10 C11 -0.2(2) . . . . ?
C5 C6 C10 C11 179.86(14) . . . . ?
C6 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C10 C11 C12 C17 -179.92(14) . . . . ?
C6 C7 C13 C14 -179.80(13) . . . . ?
C8 C7 C13 C14 0.2(2) . . . . ?
C6 C7 C13 C12 0.2(2) . . . . ?
C8 C7 C13 C12 -179.79(12) . . . . ?
C11 C12 C13 C14 -179.92(14) . . . . ?
C17 C12 C13 C14 -0.4(2) . . . . ?
C11 C12 C13 C7 0.0(2) . . . . ?
C17 C12 C13 C7 179.56(13) . . . . ?
C7 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C15 179.98(13) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C7 C8 C16 C15 0.1(2) . . . . ?
C9 C8 C16 C15 -179.97(13) . . . . ?
C14 C15 C16 C8 0.1(2) . . . . ?
C11 C12 C17 C18 -10.8(2) . . . . ?
C13 C12 C17 C18 169.71(14) . . . . ?
C12 C17 C18 C19 178.48(14) . . . . ?
C17 C18 C19 C20 -171.00(15) . . . . ?
C17 C18 C19 C24 8.7(2) . . . . ?
C24 C19 C20 C21 -0.5(2) . . . . ?
C18 C19 C20 C21 179.17(13) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C25 O3 C22 C21 -4.4(2) . . . . ?
C25 O3 C22 C23 175.12(13) . . . . ?
C20 C21 C22 O3 179.96(13) . . . . ?
C20 C21 C22 C23 0.5(2) . . . . ?
O3 C22 C23 C24 -179.97(14) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C19 -0.1(2) . . . . ?
C20 C19 C24 C23 0.6(2) . . . . ?
C18 C19 C24 C23 -179.11(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_ts138
_database_code_depnum_ccdc_archive 'CCDC 1037167'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H25 N O4'
_chemical_formula_sum            'C26 H25 N O4'
_chemical_formula_weight         415.47

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   12.6799(7)
_cell_length_b                   9.0474(5)
_cell_length_c                   18.8990(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.1260(10)
_cell_angle_gamma                90.00
_cell_volume                     2111.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4724
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      30.04

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9716
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27473
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         30.05
_reflns_number_total             6178
_reflns_number_gt                4348
_reflns_threshold_expression     I>2u(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998)'

_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)+(0.0251P)²+1.3923P] 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         6178
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1024
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.48766(8) 0.50994(12) 0.69663(5) 0.0282(2) Uani 1 1 d . . .
O2 O 0.77158(9) 0.19982(13) 0.77587(6) 0.0327(3) Uani 1 1 d . . .
O3 O 0.58306(8) 1.00321(12) 1.34553(5) 0.0276(2) Uani 1 1 d . . .
O4 O 0.69891(9) 0.78121(12) 1.32526(5) 0.0297(2) Uani 1 1 d . . .
N1 N 0.62422(9) 0.34660(13) 0.73730(6) 0.0203(2) Uani 1 1 d . . .
C1 C 0.68421(16) 0.4095(2) 0.48470(9) 0.0409(4) Uani 1 1 d . . .
H1A H 0.6592 0.3710 0.4353 0.061 Uiso 1 1 calc R . .
H1B H 0.7630 0.3986 0.5000 0.061 Uiso 1 1 calc R . .
H1C H 0.6649 0.5142 0.4857 0.061 Uiso 1 1 calc R . .
C2 C 0.63072(14) 0.32352(19) 0.53619(8) 0.0330(4) Uani 1 1 d . . .
H2A H 0.5512 0.3357 0.5203 0.040 Uiso 1 1 calc R . .
H2B H 0.6472 0.2172 0.5326 0.040 Uiso 1 1 calc R . .
C3 C 0.66617(15) 0.37056(19) 0.61479(8) 0.0340(4) Uani 1 1 d . . .
H3A H 0.6516 0.4774 0.6187 0.041 Uiso 1 1 calc R . .
H3B H 0.7452 0.3549 0.6317 0.041 Uiso 1 1 calc R . .
C4 C 0.60771(12) 0.28470(16) 0.66339(7) 0.0246(3) Uani 1 1 d . . .
H4A H 0.5292 0.2838 0.6408 0.030 Uiso 1 1 calc R . .
H4B H 0.6335 0.1811 0.6668 0.030 Uiso 1 1 calc R . .
C5 C 0.55528(11) 0.46078(15) 0.74784(7) 0.0206(3) Uani 1 1 d . . .
C6 C 0.56640(11) 0.51496(15) 0.82313(7) 0.0194(3) Uani 1 1 d . . .
C7 C 0.64759(10) 0.45745(15) 0.88047(7) 0.0178(2) Uani 1 1 d . . .
C8 C 0.71862(11) 0.34732(15) 0.86607(7) 0.0202(3) Uani 1 1 d . . .
C9 C 0.70921(11) 0.29094(16) 0.79095(7) 0.0216(3) Uani 1 1 d . . .
C10 C 0.49512(12) 0.61880(16) 0.83776(8) 0.0259(3) Uani 1 1 d . . .
H10A H 0.4395 0.6556 0.7994 0.031 Uiso 1 1 calc R . .
C11 C 0.50354(13) 0.67088(17) 0.90855(8) 0.0283(3) Uani 1 1 d . . .
H11A H 0.4534 0.7429 0.9171 0.034 Uiso 1 1 calc R . .
C12 C 0.58298(11) 0.62046(16) 0.96672(7) 0.0224(3) Uani 1 1 d . . .
C13 C 0.65655(11) 0.50875(15) 0.95319(7) 0.0196(3) Uani 1 1 d . . .
C14 C 0.73740(12) 0.44397(17) 1.00879(7) 0.0246(3) Uani 1 1 d . . .
H14A H 0.7447 0.4753 1.0576 0.030 Uiso 1 1 calc R . .
C15 C 0.80520(12) 0.33712(18) 0.99337(8) 0.0290(3) Uani 1 1 d . . .
H15A H 0.8588 0.2955 1.0316 0.035 Uiso 1 1 calc R . .
C16 C 0.79668(12) 0.28819(17) 0.92177(8) 0.0263(3) Uani 1 1 d . . .
H16A H 0.8446 0.2145 0.9117 0.032 Uiso 1 1 calc R . .
C17 C 0.59235(12) 0.67802(17) 1.04058(7) 0.0262(3) Uani 1 1 d . . .
H17A H 0.6500 0.6398 1.0772 0.031 Uiso 1 1 calc R . .
C18 C 0.52887(12) 0.77778(17) 1.06178(7) 0.0252(3) Uani 1 1 d . . .
H18A H 0.4703 0.8154 1.0257 0.030 Uiso 1 1 calc R . .
C19 C 0.54121(11) 0.83488(16) 1.13583(7) 0.0217(3) Uani 1 1 d . . .
C20 C 0.47504(11) 0.94898(16) 1.14886(7) 0.0232(3) Uani 1 1 d . . .
H20A H 0.4213 0.9873 1.1097 0.028 Uiso 1 1 calc R . .
C21 C 0.48580(11) 1.00883(16) 1.21837(7) 0.0221(3) Uani 1 1 d . . .
H21A H 0.4401 1.0874 1.2262 0.027 Uiso 1 1 calc R . .
C22 C 0.56337(11) 0.95292(15) 1.27567(7) 0.0208(3) Uani 1 1 d . . .
C23 C 0.62880(11) 0.83288(16) 1.26417(7) 0.0215(3) Uani 1 1 d . . .
C24 C 0.61819(11) 0.77613(16) 1.19507(7) 0.0222(3) Uani 1 1 d . . .
H24A H 0.6632 0.6966 1.1873 0.027 Uiso 1 1 calc R . .
C25 C 0.51202(15) 1.11485(19) 1.36113(9) 0.0376(4) Uani 1 1 d . . .
H25A H 0.5290 1.1347 1.4135 0.056 Uiso 1 1 calc R . .
H25B H 0.4369 1.0809 1.3457 0.056 Uiso 1 1 calc R . .
H25C H 0.5214 1.2056 1.3349 0.056 Uiso 1 1 calc R . .
C26 C 0.74939(12) 0.64173(18) 1.31940(9) 0.0312(3) Uani 1 1 d . . .
H26A H 0.7885 0.6092 1.3677 0.047 Uiso 1 1 calc R . .
H26B H 0.8004 0.6519 1.2877 0.047 Uiso 1 1 calc R . .
H26C H 0.6939 0.5686 1.2987 0.047 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 C5 1.2218(16) . ?
O2 C9 1.2201(17) . ?
O3 C22 1.3648(16) . ?
O3 C25 1.4279(18) . ?
O4 C23 1.3696(16) . ?
O4 C26 1.4307(18) . ?
N1 C9 1.3953(18) . ?
N1 C5 1.3965(18) . ?
N1 C4 1.4750(16) . ?
C1 C2 1.520(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.512(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.4812(18) . ?
C6 C10 1.375(2) . ?
C6 C7 1.4135(18) . ?
C7 C8 1.4104(19) . ?
C7 C13 1.4305(18) . ?
C8 C16 1.3787(19) . ?
C8 C9 1.4876(18) . ?
C10 C11 1.399(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.4372(19) . ?
C12 C17 1.4692(19) . ?
C13 C14 1.4175(19) . ?
C14 C15 1.368(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.404(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.330(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.4665(19) . ?
C18 H18A 0.9500 . ?
C19 C20 1.387(2) . ?
C19 C24 1.4116(19) . ?
C20 C21 1.3987(19) . ?
C20 H20A 0.9500 . ?
C21 C22 1.3829(19) . ?
C21 H21A 0.9500 . ?
C22 C23 1.4132(19) . ?
C23 C24 1.3810(19) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 O3 C25 116.75(11) . . ?
C23 O4 C26 116.87(11) . . ?
C9 N1 C5 124.65(11) . . ?
C9 N1 C4 118.11(12) . . ?
C5 N1 C4 117.20(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 114.11(14) . . ?
C3 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 C4 111.91(13) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C3 113.25(12) . . ?
N1 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 N1 120.38(12) . . ?
O1 C5 C6 122.49(13) . . ?
N1 C5 C6 117.11(11) . . ?
C10 C6 C7 119.68(12) . . ?
C10 C6 C5 119.72(12) . . ?
C7 C6 C5 120.57(12) . . ?
C8 C7 C6 119.87(12) . . ?
C8 C7 C13 119.98(12) . . ?
C6 C7 C13 120.15(12) . . ?
C16 C8 C7 120.40(12) . . ?
C16 C8 C9 118.93(13) . . ?
C7 C8 C9 120.66(12) . . ?
O2 C9 N1 120.58(12) . . ?
O2 C9 C8 122.61(13) . . ?
N1 C9 C8 116.81(12) . . ?
C6 C10 C11 120.76(13) . . ?
C6 C10 H10A 119.6 . . ?
C11 C10 H10A 119.6 . . ?
C12 C11 C10 122.03(14) . . ?
C12 C11 H11A 119.0 . . ?
C10 C11 H11A 119.0 . . ?
C11 C12 C13 118.27(12) . . ?
C11 C12 C17 121.56(13) . . ?
C13 C12 C17 120.17(13) . . ?
C14 C13 C7 117.67(13) . . ?
C14 C13 C12 123.25(12) . . ?
C7 C13 C12 119.07(12) . . ?
C15 C14 C13 121.18(13) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C14 C15 C16 120.89(13) . . ?
C14 C15 H15A 119.6 . . ?
C16 C15 H15A 119.6 . . ?
C8 C16 C15 119.88(14) . . ?
C8 C16 H16A 120.1 . . ?
C15 C16 H16A 120.1 . . ?
C18 C17 C12 127.06(14) . . ?
C18 C17 H17A 116.5 . . ?
C12 C17 H17A 116.5 . . ?
C17 C18 C19 125.85(14) . . ?
C17 C18 H18A 117.1 . . ?
C19 C18 H18A 117.1 . . ?
C20 C19 C24 118.46(12) . . ?
C20 C19 C18 119.60(13) . . ?
C24 C19 C18 121.94(13) . . ?
C19 C20 C21 121.39(13) . . ?
C19 C20 H20A 119.3 . . ?
C21 C20 H20A 119.3 . . ?
C22 C21 C20 119.62(13) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
O3 C22 C21 125.24(13) . . ?
O3 C22 C23 114.85(12) . . ?
C21 C22 C23 119.91(12) . . ?
O4 C23 C24 125.13(13) . . ?
O4 C23 C22 115.08(12) . . ?
C24 C23 C22 119.78(13) . . ?
C23 C24 C19 120.76(13) . . ?
C23 C24 H24A 119.6 . . ?
C19 C24 H24A 119.6 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 178.17(15) . . . . ?
C9 N1 C4 C3 -92.52(16) . . . . ?
C5 N1 C4 C3 85.42(16) . . . . ?
C2 C3 C4 N1 -168.88(14) . . . . ?
C9 N1 C5 O1 174.81(13) . . . . ?
C4 N1 C5 O1 -2.98(19) . . . . ?
C9 N1 C5 C6 -6.78(19) . . . . ?
C4 N1 C5 C6 175.43(12) . . . . ?
O1 C5 C6 C10 3.6(2) . . . . ?
N1 C5 C6 C10 -174.81(13) . . . . ?
O1 C5 C6 C7 -178.42(13) . . . . ?
N1 C5 C6 C7 3.21(19) . . . . ?
C10 C6 C7 C8 177.90(13) . . . . ?
C5 C6 C7 C8 -0.12(19) . . . . ?
C10 C6 C7 C13 -1.0(2) . . . . ?
C5 C6 C7 C13 -178.98(12) . . . . ?
C6 C7 C8 C16 -178.65(13) . . . . ?
C13 C7 C8 C16 0.2(2) . . . . ?
C6 C7 C8 C9 0.11(19) . . . . ?
C13 C7 C8 C9 178.97(12) . . . . ?
C5 N1 C9 O2 -173.62(13) . . . . ?
C4 N1 C9 O2 4.1(2) . . . . ?
C5 N1 C9 C8 6.75(19) . . . . ?
C4 N1 C9 C8 -175.48(12) . . . . ?
C16 C8 C9 O2 -4.0(2) . . . . ?
C7 C8 C9 O2 177.20(13) . . . . ?
C16 C8 C9 N1 175.60(13) . . . . ?
C7 C8 C9 N1 -3.18(19) . . . . ?
C7 C6 C10 C11 1.5(2) . . . . ?
C5 C6 C10 C11 179.55(14) . . . . ?
C6 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
C10 C11 C12 C17 178.80(15) . . . . ?
C8 C7 C13 C14 -0.70(19) . . . . ?
C6 C7 C13 C14 178.16(12) . . . . ?
C8 C7 C13 C12 -179.66(12) . . . . ?
C6 C7 C13 C12 -0.81(19) . . . . ?
C11 C12 C13 C14 -176.90(14) . . . . ?
C17 C12 C13 C14 2.8(2) . . . . ?
C11 C12 C13 C7 2.0(2) . . . . ?
C17 C12 C13 C7 -178.31(13) . . . . ?
C7 C13 C14 C15 0.6(2) . . . . ?
C12 C13 C14 C15 179.53(14) . . . . ?
C13 C14 C15 C16 0.0(2) . . . . ?
C7 C8 C16 C15 0.4(2) . . . . ?
C9 C8 C16 C15 -178.39(14) . . . . ?
C14 C15 C16 C8 -0.5(2) . . . . ?
C11 C12 C17 C18 1.6(2) . . . . ?
C13 C12 C17 C18 -178.04(15) . . . . ?
C12 C17 C18 C19 -179.01(14) . . . . ?
C17 C18 C19 C20 174.02(15) . . . . ?
C17 C18 C19 C24 -6.6(2) . . . . ?
C24 C19 C20 C21 2.1(2) . . . . ?
C18 C19 C20 C21 -178.55(13) . . . . ?
C19 C20 C21 C22 -0.5(2) . . . . ?
C25 O3 C22 C21 5.0(2) . . . . ?
C25 O3 C22 C23 -174.18(13) . . . . ?
C20 C21 C22 O3 178.85(13) . . . . ?
C20 C21 C22 C23 -2.0(2) . . . . ?
C26 O4 C23 C24 -12.6(2) . . . . ?
C26 O4 C23 C22 166.89(13) . . . . ?
O3 C22 C23 O4 2.56(18) . . . . ?
C21 C22 C23 O4 -176.66(13) . . . . ?
O3 C22 C23 C24 -177.95(13) . . . . ?
C21 C22 C23 C24 2.8(2) . . . . ?
O4 C23 C24 C19 178.25(13) . . . . ?
C22 C23 C24 C19 -1.2(2) . . . . ?
C20 C19 C24 C23 -1.2(2) . . . . ?
C18 C19 C24 C23 179.40(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.05
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_ts143
_database_code_depnum_ccdc_archive 'CCDC 1037168'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2016-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H26 N2 O2'
_chemical_formula_sum            'C26 H26 N2 O2'
_chemical_formula_weight         398.49

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4660(13)
_cell_length_b                   13.752(2)
_cell_length_c                   20.182(3)
_cell_angle_alpha                82.470(4)
_cell_angle_beta                 84.186(4)
_cell_angle_gamma                89.182(4)
_cell_volume                     2043.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2196
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      30.54

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9782
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0599
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.02
_diffrn_reflns_theta_max         26.00
_reflns_number_total             7886
_reflns_number_gt                5203
_reflns_threshold_expression     I>2u(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998)'

_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)+(0.0719P)²+0.0000P] 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         7886
_refine_ls_number_parameters     547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1413
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.9597(2) 0.22232(11) 0.31180(7) 0.0236(4) Uani 1 1 d . . .
O2 O 0.8090(2) 0.54048(11) 0.32807(8) 0.0269(4) Uani 1 1 d . . .
N1 N 0.8780(2) 0.38053(12) 0.32037(8) 0.0180(4) Uani 1 1 d . . .
N2 N 0.5820(2) 0.31315(13) -0.30088(9) 0.0210(4) Uani 1 1 d . . .
C1 C 1.2557(4) 0.40005(19) 0.51054(13) 0.0375(7) Uani 1 1 d . . .
H1A H 1.2638 0.3760 0.5580 0.056 Uiso 1 1 calc R . .
H1B H 1.2561 0.4719 0.5042 0.056 Uiso 1 1 calc R . .
H1C H 1.3589 0.3759 0.4833 0.056 Uiso 1 1 calc R . .
C2 C 1.0816(3) 0.36317(17) 0.48885(11) 0.0283(6) Uani 1 1 d . . .
H2A H 1.0812 0.2906 0.4961 0.034 Uiso 1 1 calc R . .
H2B H 0.9781 0.3862 0.5174 0.034 Uiso 1 1 calc R . .
C3 C 1.0584(3) 0.39805(16) 0.41563(10) 0.0215(5) Uani 1 1 d . . .
H3A H 1.0608 0.4706 0.4083 0.026 Uiso 1 1 calc R . .
H3B H 1.1611 0.3742 0.3871 0.026 Uiso 1 1 calc R . .
C4 C 0.8845(3) 0.36305(16) 0.39389(10) 0.0227(5) Uani 1 1 d . . .
H4A H 0.8706 0.2919 0.4093 0.027 Uiso 1 1 calc R . .
H4B H 0.7820 0.3973 0.4159 0.027 Uiso 1 1 calc R . .
C5 C 0.9111(3) 0.30141(15) 0.28421(10) 0.0176(5) Uani 1 1 d . . .
C6 C 0.8846(3) 0.31812(15) 0.21199(10) 0.0160(4) Uani 1 1 d . . .
C7 C 0.8446(3) 0.41269(15) 0.18067(10) 0.0159(4) Uani 1 1 d . . .
C8 C 0.8184(3) 0.49166(15) 0.21935(10) 0.0161(4) Uani 1 1 d . . .
C9 C 0.8337(3) 0.47518(16) 0.29262(11) 0.0194(5) Uani 1 1 d . . .
C10 C 0.8973(3) 0.24002(15) 0.17521(10) 0.0171(5) Uani 1 1 d . . .
H10B H 0.9241 0.1763 0.1963 0.021 Uiso 1 1 calc R . .
C11 C 0.8708(3) 0.25432(15) 0.10707(10) 0.0177(5) Uani 1 1 d . . .
H11A H 0.8765 0.1992 0.0830 0.021 Uiso 1 1 calc R . .
C12 C 0.8365(3) 0.34591(15) 0.07324(10) 0.0155(4) Uani 1 1 d . . .
C13 C 0.8231(3) 0.42832(15) 0.11086(10) 0.0156(4) Uani 1 1 d . . .
C14 C 0.7776(3) 0.52383(15) 0.08280(11) 0.0172(5) Uani 1 1 d . . .
H14A H 0.7632 0.5361 0.0362 0.021 Uiso 1 1 calc R . .
C15 C 0.7534(3) 0.59955(15) 0.12098(11) 0.0194(5) Uani 1 1 d . . .
H15B H 0.7231 0.6631 0.1007 0.023 Uiso 1 1 calc R . .
C16 C 0.7734(3) 0.58315(15) 0.18994(11) 0.0189(5) Uani 1 1 d . . .
H16A H 0.7558 0.6355 0.2163 0.023 Uiso 1 1 calc R . .
C17 C 0.8097(3) 0.35851(15) 0.00154(10) 0.0174(5) Uani 1 1 d . . .
H17A H 0.8484 0.4182 -0.0249 0.021 Uiso 1 1 calc R . .
C18 C 0.7339(3) 0.29094(15) -0.02892(11) 0.0180(5) Uani 1 1 d . . .
H18A H 0.6976 0.2317 -0.0015 0.022 Uiso 1 1 calc R . .
C19 C 0.7007(3) 0.29795(15) -0.09951(10) 0.0150(4) Uani 1 1 d . . .
C20 C 0.6010(3) 0.22477(15) -0.12135(10) 0.0163(4) Uani 1 1 d . . .
H20B H 0.5591 0.1705 -0.0898 0.020 Uiso 1 1 calc R . .
C21 C 0.5613(3) 0.22851(15) -0.18688(10) 0.0170(5) Uani 1 1 d . . .
H21A H 0.4922 0.1776 -0.1993 0.020 Uiso 1 1 calc R . .
C22 C 0.6224(3) 0.30724(15) -0.23567(10) 0.0164(4) Uani 1 1 d . . .
C23 C 0.7273(3) 0.38023(15) -0.21443(10) 0.0169(4) Uani 1 1 d . . .
H23A H 0.7732 0.4335 -0.2461 0.020 Uiso 1 1 calc R . .
C24 C 0.7638(3) 0.37491(15) -0.14817(10) 0.0173(5) Uani 1 1 d . . .
H24B H 0.8339 0.4251 -0.1354 0.021 Uiso 1 1 calc R . .
C25 C 0.4827(3) 0.23568(17) -0.32276(11) 0.0270(5) Uani 1 1 d . . .
H25A H 0.3639 0.2291 -0.2970 0.040 Uiso 1 1 calc R . .
H25B H 0.5487 0.1737 -0.3154 0.040 Uiso 1 1 calc R . .
H25C H 0.4680 0.2517 -0.3707 0.040 Uiso 1 1 calc R . .
C26 C 0.6452(3) 0.39576(17) -0.34953(11) 0.0289(6) Uani 1 1 d . . .
H26A H 0.6037 0.4570 -0.3331 0.043 Uiso 1 1 calc R . .
H26B H 0.5975 0.3909 -0.3925 0.043 Uiso 1 1 calc R . .
H26C H 0.7771 0.3951 -0.3559 0.043 Uiso 1 1 calc R . .
O3 O 0.3127(2) 0.02158(11) 0.33491(8) 0.0282(4) Uani 1 1 d . . .
O4 O 0.4618(2) 0.34459(11) 0.31232(7) 0.0248(4) Uani 1 1 d . . .
N3 N 0.3789(2) 0.18407(13) 0.32431(9) 0.0187(4) Uani 1 1 d . . .
N4 N 0.0881(2) 0.10670(13) -0.29529(9) 0.0213(4) Uani 1 1 d . . .
C27 C 0.7695(4) 0.0988(2) 0.51122(13) 0.0417(7) Uani 1 1 d . . .
H27A H 0.7831 0.1079 0.5578 0.063 Uiso 1 1 calc R . .
H27B H 0.8693 0.1311 0.4815 0.063 Uiso 1 1 calc R . .
H27C H 0.7706 0.0286 0.5071 0.063 Uiso 1 1 calc R . .
C28 C 0.5916(3) 0.14358(18) 0.49131(11) 0.0298(6) Uani 1 1 d . . .
H28A H 0.4912 0.1110 0.5216 0.036 Uiso 1 1 calc R . .
H28B H 0.5894 0.2140 0.4970 0.036 Uiso 1 1 calc R . .
C29 C 0.5638(3) 0.13292(16) 0.41889(11) 0.0229(5) Uani 1 1 d . . .
H29A H 0.6642 0.1658 0.3888 0.028 Uiso 1 1 calc R . .
H29B H 0.5676 0.0624 0.4133 0.028 Uiso 1 1 calc R . .
C30 C 0.3870(3) 0.17614(17) 0.39761(10) 0.0234(5) Uani 1 1 d . . .
H30A H 0.2865 0.1344 0.4206 0.028 Uiso 1 1 calc R . .
H30B H 0.3710 0.2421 0.4119 0.028 Uiso 1 1 calc R . .
C31 C 0.3352(3) 0.09893(16) 0.29811(11) 0.0199(5) Uani 1 1 d . . .
C32 C 0.3178(3) 0.10865(15) 0.22541(10) 0.0161(4) Uani 1 1 d . . .
C33 C 0.3425(3) 0.20027(15) 0.18485(10) 0.0153(4) Uani 1 1 d . . .
C34 C 0.3873(3) 0.28392(15) 0.21399(10) 0.0161(4) Uani 1 1 d . . .
C35 C 0.4141(3) 0.27483(15) 0.28631(11) 0.0177(5) Uani 1 1 d . . .
C36 C 0.2718(3) 0.02755(15) 0.19714(11) 0.0186(5) Uani 1 1 d . . .
H36A H 0.2573 -0.0343 0.2242 0.022 Uiso 1 1 calc R . .
C37 C 0.2463(3) 0.03597(15) 0.12856(10) 0.0181(5) Uani 1 1 d . . .
H37A H 0.2135 -0.0206 0.1101 0.022 Uiso 1 1 calc R . .
C38 C 0.2676(3) 0.12434(15) 0.08715(10) 0.0164(4) Uani 1 1 d . . .
C39 C 0.3179(3) 0.20948(15) 0.11535(10) 0.0161(4) Uani 1 1 d . . .
C40 C 0.3409(3) 0.30376(15) 0.07756(11) 0.0171(5) Uani 1 1 d . . .
H40A H 0.3278 0.3116 0.0308 0.021 Uiso 1 1 calc R . .
C41 C 0.3816(3) 0.38373(15) 0.10710(11) 0.0193(5) Uani 1 1 d . . .
H41A H 0.3938 0.4463 0.0809 0.023 Uiso 1 1 calc R . .
C42 C 0.4053(3) 0.37406(15) 0.17560(11) 0.0184(5) Uani 1 1 d . . .
H42A H 0.4340 0.4300 0.1956 0.022 Uiso 1 1 calc R . .
C43 C 0.2300(3) 0.13280(15) 0.01670(10) 0.0177(5) Uani 1 1 d . . .
H43A H 0.1921 0.1953 -0.0030 0.021 Uiso 1 1 calc R . .
C44 C 0.2438(3) 0.06138(15) -0.02276(11) 0.0182(5) Uani 1 1 d . . .
H44A H 0.2862 -0.0008 -0.0043 0.022 Uiso 1 1 calc R . .
C45 C 0.1985(3) 0.07179(15) -0.09216(10) 0.0156(4) Uani 1 1 d . . .
C46 C 0.2652(3) 0.00597(15) -0.13622(10) 0.0177(5) Uani 1 1 d . . .
H46A H 0.3361 -0.0480 -0.1197 0.021 Uiso 1 1 calc R . .
C47 C 0.2313(3) 0.01702(15) -0.20277(11) 0.0198(5) Uani 1 1 d . . .
H47A H 0.2804 -0.0288 -0.2310 0.024 Uiso 1 1 calc R . .
C48 C 0.1250(3) 0.09506(15) -0.22945(11) 0.0175(5) Uani 1 1 d . . .
C49 C 0.0567(3) 0.16147(15) -0.18540(10) 0.0174(5) Uani 1 1 d . . .
H49A H -0.0152 0.2152 -0.2016 0.021 Uiso 1 1 calc R . .
C50 C 0.0930(3) 0.14931(15) -0.11931(10) 0.0169(5) Uani 1 1 d . . .
H50A H 0.0447 0.1952 -0.0910 0.020 Uiso 1 1 calc R . .
C51 C 0.1584(3) 0.03639(17) -0.33943(11) 0.0287(6) Uani 1 1 d . . .
H51A H 0.1129 -0.0292 -0.3213 0.043 Uiso 1 1 calc R . .
H51B H 0.2902 0.0361 -0.3424 0.043 Uiso 1 1 calc R . .
H51C H 0.1194 0.0550 -0.3843 0.043 Uiso 1 1 calc R . .
C52 C -0.0093(3) 0.19146(17) -0.32303(11) 0.0274(5) Uani 1 1 d . . .
H52A H 0.0504 0.2513 -0.3152 0.041 Uiso 1 1 calc R . .
H52B H -0.1329 0.1898 -0.3013 0.041 Uiso 1 1 calc R . .
H52C H -0.0115 0.1908 -0.3714 0.041 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 C5 1.223(2) . ?
O2 C9 1.220(2) . ?
N1 C5 1.393(3) . ?
N1 C9 1.397(3) . ?
N1 C4 1.477(3) . ?
N2 C22 1.372(3) . ?
N2 C25 1.446(3) . ?
N2 C26 1.451(3) . ?
C1 C2 1.526(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.519(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.516(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.478(3) . ?
C6 C10 1.380(3) . ?
C6 C7 1.411(3) . ?
C7 C8 1.419(3) . ?
C7 C13 1.422(3) . ?
C8 C16 1.371(3) . ?
C8 C9 1.482(3) . ?
C10 C11 1.397(3) . ?
C10 H10B 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.441(3) . ?
C12 C17 1.468(3) . ?
C13 C14 1.412(3) . ?
C14 C15 1.374(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.403(3) . ?
C15 H15B 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.340(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.461(3) . ?
C18 H18A 0.9500 . ?
C19 C24 1.398(3) . ?
C19 C20 1.402(3) . ?
C20 C21 1.379(3) . ?
C20 H20B 0.9500 . ?
C21 C22 1.412(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.417(3) . ?
C23 C24 1.384(3) . ?
C23 H23A 0.9500 . ?
C24 H24B 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O3 C31 1.218(3) . ?
O4 C35 1.226(2) . ?
N3 C35 1.390(3) . ?
N3 C31 1.402(3) . ?
N3 C30 1.476(3) . ?
N4 C48 1.373(3) . ?
N4 C52 1.445(3) . ?
N4 C51 1.456(3) . ?
C27 C28 1.525(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.523(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.519(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.474(3) . ?
C32 C36 1.380(3) . ?
C32 C33 1.413(3) . ?
C33 C34 1.418(3) . ?
C33 C39 1.422(3) . ?
C34 C42 1.374(3) . ?
C34 C35 1.482(3) . ?
C36 C37 1.406(3) . ?
C36 H36A 0.9500 . ?
C37 C38 1.383(3) . ?
C37 H37A 0.9500 . ?
C38 C39 1.437(3) . ?
C38 C43 1.466(3) . ?
C39 C40 1.419(3) . ?
C40 C41 1.369(3) . ?
C40 H40A 0.9500 . ?
C41 C42 1.400(3) . ?
C41 H41A 0.9500 . ?
C42 H42A 0.9500 . ?
C43 C44 1.340(3) . ?
C43 H43A 0.9500 . ?
C44 C45 1.462(3) . ?
C44 H44A 0.9500 . ?
C45 C46 1.402(3) . ?
C45 C50 1.403(3) . ?
C46 C47 1.380(3) . ?
C46 H46A 0.9500 . ?
C47 C48 1.408(3) . ?
C47 H47A 0.9500 . ?
C48 C49 1.411(3) . ?
C49 C50 1.376(3) . ?
C49 H49A 0.9500 . ?
C50 H50A 0.9500 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C9 124.90(17) . . ?
C5 N1 C4 117.98(17) . . ?
C9 N1 C4 117.09(17) . . ?
C22 N2 C25 120.72(18) . . ?
C22 N2 C26 120.10(17) . . ?
C25 N2 C26 119.13(17) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 112.7(2) . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 113.08(19) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C3 112.90(18) . . ?
N1 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
O1 C5 N1 120.67(19) . . ?
O1 C5 C6 122.41(19) . . ?
N1 C5 C6 116.92(18) . . ?
C10 C6 C7 119.89(19) . . ?
C10 C6 C5 119.45(19) . . ?
C7 C6 C5 120.65(18) . . ?
C6 C7 C8 120.01(19) . . ?
C6 C7 C13 120.18(18) . . ?
C8 C7 C13 119.76(19) . . ?
C16 C8 C7 120.57(19) . . ?
C16 C8 C9 119.28(18) . . ?
C7 C8 C9 120.12(19) . . ?
O2 C9 N1 120.45(19) . . ?
O2 C9 C8 122.4(2) . . ?
N1 C9 C8 117.16(18) . . ?
C6 C10 C11 120.20(19) . . ?
C6 C10 H10B 119.9 . . ?
C11 C10 H10B 119.9 . . ?
C12 C11 C10 122.42(19) . . ?
C12 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
C11 C12 C13 118.09(18) . . ?
C11 C12 C17 121.08(18) . . ?
C13 C12 C17 120.81(18) . . ?
C14 C13 C7 117.60(18) . . ?
C14 C13 C12 123.11(18) . . ?
C7 C13 C12 119.16(18) . . ?
C15 C14 C13 121.85(19) . . ?
C15 C14 H14A 119.1 . . ?
C13 C14 H14A 119.1 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15B 119.9 . . ?
C16 C15 H15B 119.9 . . ?
C8 C16 C15 120.12(19) . . ?
C8 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C18 C17 C12 124.0(2) . . ?
C18 C17 H17A 118.0 . . ?
C12 C17 H17A 118.0 . . ?
C17 C18 C19 127.5(2) . . ?
C17 C18 H18A 116.3 . . ?
C19 C18 H18A 116.3 . . ?
C24 C19 C20 116.66(18) . . ?
C24 C19 C18 123.51(18) . . ?
C20 C19 C18 119.83(19) . . ?
C21 C20 C19 122.54(19) . . ?
C21 C20 H20B 118.7 . . ?
C19 C20 H20B 118.7 . . ?
C20 C21 C22 120.66(19) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
N2 C22 C21 121.57(18) . . ?
N2 C22 C23 121.25(19) . . ?
C21 C22 C23 117.18(18) . . ?
C24 C23 C22 120.85(19) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
C23 C24 C19 122.07(18) . . ?
C23 C24 H24B 119.0 . . ?
C19 C24 H24B 119.0 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C35 N3 C31 124.69(17) . . ?
C35 N3 C30 118.09(17) . . ?
C31 N3 C30 117.21(18) . . ?
C48 N4 C52 121.06(17) . . ?
C48 N4 C51 119.80(18) . . ?
C52 N4 C51 119.00(18) . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C28 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C28 C27 112.0(2) . . ?
C29 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C29 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C30 C29 C28 113.29(19) . . ?
C30 C29 H29A 108.9 . . ?
C28 C29 H29A 108.9 . . ?
C30 C29 H29B 108.9 . . ?
C28 C29 H29B 108.9 . . ?
H29A C29 H29B 107.7 . . ?
N3 C30 C29 112.45(18) . . ?
N3 C30 H30A 109.1 . . ?
C29 C30 H30A 109.1 . . ?
N3 C30 H30B 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.8 . . ?
O3 C31 N3 120.20(19) . . ?
O3 C31 C32 122.92(19) . . ?
N3 C31 C32 116.88(18) . . ?
C36 C32 C33 119.74(19) . . ?
C36 C32 C31 119.33(19) . . ?
C33 C32 C31 120.91(18) . . ?
C32 C33 C34 119.80(18) . . ?
C32 C33 C39 120.33(18) . . ?
C34 C33 C39 119.85(19) . . ?
C42 C34 C33 120.34(19) . . ?
C42 C34 C35 119.48(18) . . ?
C33 C34 C35 120.18(18) . . ?
O4 C35 N3 120.86(19) . . ?
O4 C35 C34 121.82(19) . . ?
N3 C35 C34 117.30(17) . . ?
C32 C36 C37 120.38(19) . . ?
C32 C36 H36A 119.8 . . ?
C37 C36 H36A 119.8 . . ?
C38 C37 C36 121.80(19) . . ?
C38 C37 H37A 119.1 . . ?
C36 C37 H37A 119.1 . . ?
C37 C38 C39 118.75(18) . . ?
C37 C38 C43 120.91(18) . . ?
C39 C38 C43 120.26(18) . . ?
C40 C39 C33 117.72(18) . . ?
C40 C39 C38 123.27(18) . . ?
C33 C39 C38 119.00(19) . . ?
C41 C40 C39 121.31(19) . . ?
C41 C40 H40A 119.3 . . ?
C39 C40 H40A 119.3 . . ?
C40 C41 C42 120.6(2) . . ?
C40 C41 H41A 119.7 . . ?
C42 C41 H41A 119.7 . . ?
C34 C42 C41 120.15(19) . . ?
C34 C42 H42A 119.9 . . ?
C41 C42 H42A 119.9 . . ?
C44 C43 C38 126.6(2) . . ?
C44 C43 H43A 116.7 . . ?
C38 C43 H43A 116.7 . . ?
C43 C44 C45 125.0(2) . . ?
C43 C44 H44A 117.5 . . ?
C45 C44 H44A 117.5 . . ?
C46 C45 C50 116.18(19) . . ?
C46 C45 C44 121.20(19) . . ?
C50 C45 C44 122.57(18) . . ?
C47 C46 C45 122.2(2) . . ?
C47 C46 H46A 118.9 . . ?
C45 C46 H46A 118.9 . . ?
C46 C47 C48 121.10(19) . . ?
C46 C47 H47A 119.5 . . ?
C48 C47 H47A 119.5 . . ?
N4 C48 C47 121.98(19) . . ?
N4 C48 C49 120.94(19) . . ?
C47 C48 C49 117.08(19) . . ?
C50 C49 C48 120.83(19) . . ?
C50 C49 H49A 119.6 . . ?
C48 C49 H49A 119.6 . . ?
C49 C50 C45 122.59(19) . . ?
C49 C50 H50A 118.7 . . ?
C45 C50 H50A 118.7 . . ?
N4 C51 H51A 109.5 . . ?
N4 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
N4 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N4 C52 H52A 109.5 . . ?
N4 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
N4 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -179.14(19) . . . . ?
C5 N1 C4 C3 101.7(2) . . . . ?
C9 N1 C4 C3 -80.1(2) . . . . ?
C2 C3 C4 N1 -168.95(18) . . . . ?
C9 N1 C5 O1 175.6(2) . . . . ?
C4 N1 C5 O1 -6.3(3) . . . . ?
C9 N1 C5 C6 -4.5(3) . . . . ?
C4 N1 C5 C6 173.59(18) . . . . ?
O1 C5 C6 C10 6.6(3) . . . . ?
N1 C5 C6 C10 -173.35(19) . . . . ?
O1 C5 C6 C7 -174.14(19) . . . . ?
N1 C5 C6 C7 5.9(3) . . . . ?
C10 C6 C7 C8 175.3(2) . . . . ?
C5 C6 C7 C8 -3.9(3) . . . . ?
C10 C6 C7 C13 -2.0(3) . . . . ?
C5 C6 C7 C13 178.69(18) . . . . ?
C6 C7 C8 C16 -177.77(19) . . . . ?
C13 C7 C8 C16 -0.4(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C13 C7 C8 C9 177.65(18) . . . . ?
C5 N1 C9 O2 -179.1(2) . . . . ?
C4 N1 C9 O2 2.8(3) . . . . ?
C5 N1 C9 C8 1.0(3) . . . . ?
C4 N1 C9 C8 -177.10(18) . . . . ?
C16 C8 C9 O2 -0.5(3) . . . . ?
C7 C8 C9 O2 -178.6(2) . . . . ?
C16 C8 C9 N1 179.37(18) . . . . ?
C7 C8 C9 N1 1.3(3) . . . . ?
C7 C6 C10 C11 0.1(3) . . . . ?
C5 C6 C10 C11 179.35(19) . . . . ?
C6 C10 C11 C12 1.9(3) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
C10 C11 C12 C17 179.87(19) . . . . ?
C6 C7 C13 C14 178.03(19) . . . . ?
C8 C7 C13 C14 0.7(3) . . . . ?
C6 C7 C13 C12 2.1(3) . . . . ?
C8 C7 C13 C12 -175.27(18) . . . . ?
C11 C12 C13 C14 -175.9(2) . . . . ?
C17 C12 C13 C14 2.4(3) . . . . ?
C11 C12 C13 C7 -0.2(3) . . . . ?
C17 C12 C13 C7 178.14(18) . . . . ?
C7 C13 C14 C15 -0.4(3) . . . . ?
C12 C13 C14 C15 175.4(2) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C7 C8 C16 C15 -0.2(3) . . . . ?
C9 C8 C16 C15 -178.23(19) . . . . ?
C14 C15 C16 C8 0.4(3) . . . . ?
C11 C12 C17 C18 32.5(3) . . . . ?
C13 C12 C17 C18 -145.8(2) . . . . ?
C12 C17 C18 C19 179.35(19) . . . . ?
C17 C18 C19 C24 7.5(3) . . . . ?
C17 C18 C19 C20 -172.6(2) . . . . ?
C24 C19 C20 C21 -1.8(3) . . . . ?
C18 C19 C20 C21 178.34(19) . . . . ?
C19 C20 C21 C22 0.7(3) . . . . ?
C25 N2 C22 C21 -3.3(3) . . . . ?
C26 N2 C22 C21 179.2(2) . . . . ?
C25 N2 C22 C23 176.8(2) . . . . ?
C26 N2 C22 C23 -0.7(3) . . . . ?
C20 C21 C22 N2 -178.93(19) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
N2 C22 C23 C24 178.42(19) . . . . ?
C21 C22 C23 C24 -1.5(3) . . . . ?
C22 C23 C24 C19 0.4(3) . . . . ?
C20 C19 C24 C23 1.3(3) . . . . ?
C18 C19 C24 C23 -178.87(19) . . . . ?
C27 C28 C29 C30 179.6(2) . . . . ?
C35 N3 C30 C29 -99.5(2) . . . . ?
C31 N3 C30 C29 80.8(2) . . . . ?
C28 C29 C30 N3 167.95(18) . . . . ?
C35 N3 C31 O3 177.3(2) . . . . ?
C30 N3 C31 O3 -2.9(3) . . . . ?
C35 N3 C31 C32 -2.9(3) . . . . ?
C30 N3 C31 C32 176.81(18) . . . . ?
O3 C31 C32 C36 0.9(3) . . . . ?
N3 C31 C32 C36 -178.84(19) . . . . ?
O3 C31 C32 C33 179.1(2) . . . . ?
N3 C31 C32 C33 -0.7(3) . . . . ?
C36 C32 C33 C34 179.13(19) . . . . ?
C31 C32 C33 C34 1.0(3) . . . . ?
C36 C32 C33 C39 0.8(3) . . . . ?
C31 C32 C33 C39 -177.35(19) . . . . ?
C32 C33 C34 C42 -177.67(19) . . . . ?
C39 C33 C34 C42 0.7(3) . . . . ?
C32 C33 C34 C35 2.0(3) . . . . ?
C39 C33 C34 C35 -179.67(18) . . . . ?
C31 N3 C35 O4 -175.7(2) . . . . ?
C30 N3 C35 O4 4.6(3) . . . . ?
C31 N3 C35 C34 5.8(3) . . . . ?
C30 N3 C35 C34 -173.94(18) . . . . ?
C42 C34 C35 O4 -4.1(3) . . . . ?
C33 C34 C35 O4 176.25(19) . . . . ?
C42 C34 C35 N3 174.46(18) . . . . ?
C33 C34 C35 N3 -5.2(3) . . . . ?
C33 C32 C36 C37 -1.1(3) . . . . ?
C31 C32 C36 C37 177.05(19) . . . . ?
C32 C36 C37 C38 0.6(3) . . . . ?
C36 C37 C38 C39 0.2(3) . . . . ?
C36 C37 C38 C43 -176.38(19) . . . . ?
C32 C33 C39 C40 178.70(18) . . . . ?
C34 C33 C39 C40 0.4(3) . . . . ?
C32 C33 C39 C38 0.1(3) . . . . ?
C34 C33 C39 C38 -178.28(18) . . . . ?
C37 C38 C39 C40 -179.12(19) . . . . ?
C43 C38 C39 C40 -2.5(3) . . . . ?
C37 C38 C39 C33 -0.6(3) . . . . ?
C43 C38 C39 C33 176.08(18) . . . . ?
C33 C39 C40 C41 -1.4(3) . . . . ?
C38 C39 C40 C41 177.2(2) . . . . ?
C39 C40 C41 C42 1.3(3) . . . . ?
C33 C34 C42 C41 -0.8(3) . . . . ?
C35 C34 C42 C41 179.60(19) . . . . ?
C40 C41 C42 C34 -0.2(3) . . . . ?
C37 C38 C43 C44 -28.5(3) . . . . ?
C39 C38 C43 C44 154.9(2) . . . . ?
C38 C43 C44 C45 177.6(2) . . . . ?
C43 C44 C45 C46 160.6(2) . . . . ?
C43 C44 C45 C50 -16.9(3) . . . . ?
C50 C45 C46 C47 0.7(3) . . . . ?
C44 C45 C46 C47 -176.86(19) . . . . ?
C45 C46 C47 C48 -0.8(3) . . . . ?
C52 N4 C48 C47 -175.1(2) . . . . ?
C51 N4 C48 C47 0.6(3) . . . . ?
C52 N4 C48 C49 5.1(3) . . . . ?
C51 N4 C48 C49 -179.2(2) . . . . ?
C46 C47 C48 N4 -179.27(19) . . . . ?
C46 C47 C48 C49 0.6(3) . . . . ?
N4 C48 C49 C50 179.60(19) . . . . ?
C47 C48 C49 C50 -0.2(3) . . . . ?
C48 C49 C50 C45 0.2(3) . . . . ?
C46 C45 C50 C49 -0.4(3) . . . . ?
C44 C45 C50 C49 177.15(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.064

