# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_2
_database_code_depnum_ccdc_archive 'CCDC 1056680'
_audit_update_record             
;
2015-03-28 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H22 F N, H2 O '
_chemical_formula_sum            'C38 H24 F N O'
_chemical_formula_weight         529.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.218(3)
_cell_length_b                   19.743(5)
_cell_length_c                   13.558(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.822(9)
_cell_angle_gamma                90.00
_cell_volume                     2746.9(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3445
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.21

_exptl_crystal_description       Strip
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            35710
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4810
_reflns_number_gt                2863
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.1971P)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    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4810
_refine_ls_number_parameters     367
_refine_ls_number_restraints     246
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.2472
_refine_ls_wR_factor_gt          0.2242
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.109
_refine_ls_shift/su_max          0.002
_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
N1 N 0.3017(3) 0.72369(15) 0.6324(2) 0.0434(8) Uani 1 1 d U . .
C1 C 0.4038(3) 0.73921(18) 0.5971(3) 0.0375(9) Uani 1 1 d U . .
C2 C 0.4393(3) 0.69140(17) 0.5375(3) 0.0366(9) Uani 1 1 d U . .
C3 C 0.3769(3) 0.62650(18) 0.5059(3) 0.0406(9) Uani 1 1 d U . .
H3 H 0.3096 0.6148 0.5261 0.049 Uiso 1 1 calc R . .
C4 C 0.4135(4) 0.5825(2) 0.4480(3) 0.0426(10) Uani 1 1 d U . .
H4 H 0.374(4) 0.545(2) 0.437(3) 0.051 Uiso 1 1 d . . .
C5 C 0.5175(4) 0.59604(18) 0.4154(3) 0.0416(9) Uani 1 1 d U . .
C6 C 0.5594(4) 0.5501(2) 0.3576(3) 0.0529(11) Uani 1 1 d U . .
H6 H 0.5183 0.5083 0.3382 0.063 Uiso 1 1 calc R . .
C7 C 0.6603(5) 0.5659(2) 0.3290(4) 0.0645(12) Uani 1 1 d U . .
H7 H 0.6862 0.5347 0.2902 0.077 Uiso 1 1 calc R . .
C8 C 0.7240(4) 0.6274(2) 0.3571(4) 0.0612(12) Uani 1 1 d U . .
H8 H 0.7926 0.6371 0.3374 0.073 Uiso 1 1 calc R . .
C9 C 0.6859(4) 0.6754(2) 0.4153(3) 0.0468(10) Uani 1 1 d U . .
C10 C 0.7494(4) 0.7388(2) 0.4461(4) 0.0585(11) Uani 1 1 d U . .
H10 H 0.8191 0.7492 0.4280 0.070 Uiso 1 1 calc R . .
C11 C 0.7110(4) 0.7839(2) 0.5003(3) 0.0537(11) Uani 1 1 d U . .
H11 H 0.7536 0.8254 0.5179 0.064 Uiso 1 1 calc R . .
C12 C 0.6071(4) 0.77064(18) 0.5324(3) 0.0410(9) Uani 1 1 d U . .
C13 C 0.5643(4) 0.8171(2) 0.5889(3) 0.0518(11) Uani 1 1 d U . .
H13 H 0.6032 0.8596 0.6051 0.062 Uiso 1 1 calc R . .
C14 C 0.4658(4) 0.80126(19) 0.6211(3) 0.0481(10) Uani 1 1 d U . .
H14 H 0.4406 0.8330 0.6597 0.058 Uiso 1 1 calc R . .
C15 C 0.5423(3) 0.70729(17) 0.5050(3) 0.0357(8) Uani 1 1 d U . .
C16 C 0.5814(3) 0.65982(18) 0.4442(3) 0.0382(9) Uani 1 1 d U . .
C17 C 0.2122(4) 0.77708(17) 0.6249(3) 0.0398(9) Uani 1 1 d U . .
C18 C 0.2207(4) 0.8118(2) 0.7165(3) 0.0481(10) Uani 1 1 d U . .
H18 H 0.2841 0.7996 0.7833 0.058 Uiso 1 1 calc R . .
C19 C 0.1362(4) 0.86424(19) 0.7096(3) 0.0483(10) Uani 1 1 d U . .
H19 H 0.1419 0.8859 0.7723 0.058 Uiso 1 1 calc R . .
C20 C 0.0430(3) 0.88512(18) 0.6109(3) 0.0413(9) Uani 1 1 d U . .
C21 C -0.0461(4) 0.9403(2) 0.5993(3) 0.0492(10) Uani 1 1 d U . .
H21 H -0.0432 0.9626 0.6607 0.059 Uiso 1 1 calc R . .
C22 C -0.1321(4) 0.9601(2) 0.5032(3) 0.0513(10) Uani 1 1 d U . .
H22 H -0.1860 0.9968 0.4989 0.062 Uiso 1 1 calc R . .
C23 C -0.1443(4) 0.92642(18) 0.4056(3) 0.0445(10) Uani 1 1 d U . .
C24 C -0.2335(4) 0.9463(2) 0.3036(4) 0.0590(12) Uani 1 1 d U . .
H24 H -0.2864 0.9838 0.2973 0.071 Uiso 1 1 calc R . .
C25 C -0.2445(4) 0.9118(2) 0.2127(4) 0.0636(12) Uani 1 1 d U . .
H25 H -0.3056 0.9258 0.1459 0.076 Uiso 1 1 calc R . .
C26 C -0.1667(4) 0.8567(2) 0.2186(3) 0.0539(11) Uani 1 1 d U . .
H26 H -0.1760 0.8335 0.1562 0.065 Uiso 1 1 calc R . .
C27 C -0.0729(3) 0.83538(18) 0.3191(3) 0.0425(9) Uani 1 1 d U . .
C28 C 0.0093(4) 0.77831(19) 0.3289(3) 0.0450(10) Uani 1 1 d U . .
H28 H 0.0008 0.7541 0.2676 0.054 Uiso 1 1 calc R . .
C29 C 0.0991(4) 0.75912(19) 0.4257(3) 0.0453(10) Uani 1 1 d U . .
H29 H 0.1503 0.7213 0.4297 0.054 Uiso 1 1 calc R . .
C30 C 0.1182(3) 0.79526(17) 0.5231(3) 0.0372(9) Uani 1 1 d U . .
C31 C 0.0346(3) 0.85070(17) 0.5163(3) 0.0366(9) Uani 1 1 d U . .
C32 C -0.0611(3) 0.87114(17) 0.4131(3) 0.0383(9) Uani 1 1 d U . .
C33 C 0.3222(4) 0.67259(18) 0.7115(3) 0.0403(9) Uani 1 1 d U . .
C34 C 0.2162(4) 0.6480(2) 0.7285(3) 0.0527(11) Uani 1 1 d U . .
H34 H 0.1335 0.6649 0.6875 0.063 Uiso 1 1 calc R . .
C35 C 0.2310(5) 0.5991(2) 0.8045(4) 0.0674(13) Uani 1 1 d U . .
H35 H 0.1597 0.5836 0.8165 0.081 Uiso 1 1 calc R . .
C36 C 0.3520(5) 0.5738(2) 0.8616(4) 0.0609(12) Uani 1 1 d U . .
C37 C 0.4590(4) 0.5951(2) 0.8465(3) 0.0589(12) Uani 1 1 d U . .
H37 H 0.5405 0.5762 0.8859 0.071 Uiso 1 1 calc R . .
C38 C 0.4435(4) 0.64551(19) 0.7708(3) 0.0481(10) Uani 1 1 d U . .
H38 H 0.5155 0.6611 0.7601 0.058 Uiso 1 1 calc R . .
O1W O 0.0491(3) 0.9738(2) 0.9243(3) 0.0991(13) Uani 1 1 d U . .
F1 F 0.3667(3) 0.52452(17) 0.9366(3) 0.1051(11) Uani 1 1 d U . .
H1WA H 0.0460 0.9400 0.9621 0.158 Uiso 1 1 d R . .
H2WB H 0.0633 1.0161 0.9226 0.158 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C33 1.422(4) . ?
N1 C17 1.431(5) . ?
N1 C1 1.442(5) . ?
C1 C14 1.381(5) . ?
C1 C2 1.401(5) . ?
C2 C15 1.427(5) . ?
C2 C3 1.440(5) . ?
C3 C4 1.341(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.430(5) . ?
C4 H4 0.84(4) . ?
C5 C6 1.397(5) . ?
C5 C16 1.424(5) . ?
C6 C7 1.372(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.383(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(6) . ?
C8 H8 0.9300 . ?
C9 C16 1.411(5) . ?
C9 C10 1.418(6) . ?
C10 C11 1.332(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.423(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.399(5) . ?
C12 C15 1.419(5) . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.430(5) . ?
C17 C18 1.388(5) . ?
C17 C30 1.404(5) . ?
C18 C19 1.381(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(5) . ?
C19 H19 0.9300 . ?
C20 C31 1.421(5) . ?
C20 C21 1.443(5) . ?
C21 C22 1.330(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.437(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.396(6) . ?
C23 C32 1.412(5) . ?
C24 C25 1.370(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.408(5) . ?
C26 H26 0.9300 . ?
C27 C32 1.415(5) . ?
C27 C28 1.428(5) . ?
C28 C29 1.346(5) . ?
C28 H28 0.9300 . ?
C29 C30 1.439(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.420(5) . ?
C31 C32 1.436(5) . ?
C33 C38 1.378(5) . ?
C33 C34 1.387(5) . ?
C34 C35 1.373(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.357(6) . ?
C35 H35 0.9300 . ?
C36 C37 1.363(6) . ?
C36 F1 1.368(5) . ?
C37 C38 1.389(5) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
O1W H1WA 0.8513 . ?
O1W H2WB 0.8521 . ?

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
C33 N1 C17 118.2(3) . . ?
C33 N1 C1 119.5(3) . . ?
C17 N1 C1 116.6(3) . . ?
C14 C1 C2 120.0(3) . . ?
C14 C1 N1 120.2(3) . . ?
C2 C1 N1 119.9(3) . . ?
C1 C2 C15 119.0(3) . . ?
C1 C2 C3 123.6(3) . . ?
C15 C2 C3 117.4(3) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 122.8(4) . . ?
C3 C4 H4 114(3) . . ?
C5 C4 H4 123(3) . . ?
C6 C5 C16 118.8(4) . . ?
C6 C5 C4 123.6(4) . . ?
C16 C5 C4 117.6(3) . . ?
C7 C6 C5 120.9(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C16 119.0(4) . . ?
C8 C9 C10 122.0(4) . . ?
C16 C9 C10 119.1(4) . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 122.2(4) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C15 117.9(3) . . ?
C13 C12 C11 123.4(3) . . ?
C15 C12 C11 118.6(3) . . ?
C14 C13 C12 121.4(4) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C1 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C1 C14 H14 119.4 . . ?
C12 C15 C2 120.4(3) . . ?
C12 C15 C16 119.0(3) . . ?
C2 C15 C16 120.6(3) . . ?
C9 C16 C5 119.9(3) . . ?
C9 C16 C15 120.0(3) . . ?
C5 C16 C15 120.0(3) . . ?
C18 C17 C30 120.4(3) . . ?
C18 C17 N1 120.5(3) . . ?
C30 C17 N1 119.1(3) . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.1(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C31 118.6(3) . . ?
C19 C20 C21 123.3(3) . . ?
C31 C20 C21 118.2(3) . . ?
C22 C21 C20 121.7(4) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 121.8(4) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C32 118.5(4) . . ?
C24 C23 C22 123.0(4) . . ?
C32 C23 C22 118.5(3) . . ?
C25 C24 C23 121.3(4) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C26 121.0(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C25 C26 C27 120.0(4) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C32 118.9(4) . . ?
C26 C27 C28 121.8(3) . . ?
C32 C27 C28 119.2(3) . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 122.0(3) . . ?
C28 C29 H29 119.0 . . ?
C30 C29 H29 119.0 . . ?
C17 C30 C31 118.3(3) . . ?
C17 C30 C29 123.4(3) . . ?
C31 C30 C29 118.3(3) . . ?
C20 C31 C30 120.6(3) . . ?
C20 C31 C32 119.8(3) . . ?
C30 C31 C32 119.6(3) . . ?
C27 C32 C23 120.1(3) . . ?
C27 C32 C31 119.9(3) . . ?
C23 C32 C31 120.0(3) . . ?
C38 C33 C34 118.5(3) . . ?
C38 C33 N1 122.4(3) . . ?
C34 C33 N1 119.0(3) . . ?
C35 C34 C33 121.3(4) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C36 C35 C34 118.5(4) . . ?
C36 C35 H35 120.8 . . ?
C34 C35 H35 120.8 . . ?
C35 C36 C37 122.7(4) . . ?
C35 C36 F1 118.5(4) . . ?
C37 C36 F1 118.8(4) . . ?
C36 C37 C38 118.4(4) . . ?
C36 C37 H37 120.8 . . ?
C38 C37 H37 120.8 . . ?
C33 C38 C37 120.6(4) . . ?
C33 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
H1WA O1W H2WB 147.1 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1056681'
_audit_update_record             
;
2015-03-28 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H25 N'
_chemical_formula_sum            'C39 H25 N'
_chemical_formula_weight         507.60

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'

_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                   10.979(2)
_cell_length_b                   11.264(2)
_cell_length_c                   12.763(3)
_cell_angle_alpha                115.84(3)
_cell_angle_beta                 110.99(3)
_cell_angle_gamma                90.42(3)
_cell_volume                     1300.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3245
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.56

_exptl_crystal_description       Strip
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             532
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10742
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0847
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.15
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4524
_reflns_number_gt                3233
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.0578P)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    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.178(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4524
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1119
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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
N1 N -0.06435(11) 0.42127(11) 0.18071(11) 0.0238(3) Uani 1 1 d . . .
C1 C -0.02427(14) 0.55164(14) 0.19782(13) 0.0226(3) Uani 1 1 d . . .
C2 C -0.08029(13) 0.66118(14) 0.25649(13) 0.0217(3) Uani 1 1 d . . .
C3 C -0.17593(14) 0.65204(14) 0.30678(13) 0.0240(4) Uani 1 1 d . . .
H3 H -0.2032 0.5703 0.3012 0.029 Uiso 1 1 calc R . .
C4 C -0.22726(14) 0.75915(14) 0.36197(14) 0.0252(4) Uani 1 1 d . . .
H4 H -0.2894 0.7490 0.3929 0.030 Uiso 1 1 calc R . .
C5 C -0.18881(13) 0.88761(14) 0.37426(13) 0.0227(3) Uani 1 1 d . . .
C6 C -0.23975(14) 1.00024(14) 0.43189(13) 0.0264(4) Uani 1 1 d . . .
H6 H -0.3028 0.9924 0.4627 0.032 Uiso 1 1 calc R . .
C7 C -0.19764(14) 1.12313(15) 0.44368(14) 0.0282(4) Uani 1 1 d . . .
H7 H -0.2322 1.1971 0.4827 0.034 Uiso 1 1 calc R . .
C8 C -0.10480(14) 1.13711(14) 0.39808(14) 0.0262(4) Uani 1 1 d . . .
H8 H -0.0782 1.2203 0.4061 0.031 Uiso 1 1 calc R . .
C9 C -0.05025(14) 1.02809(14) 0.34000(13) 0.0233(3) Uani 1 1 d . . .
C10 C 0.05019(15) 1.04066(15) 0.29607(14) 0.0270(4) Uani 1 1 d . . .
H10 H 0.0773 1.1228 0.3024 0.032 Uiso 1 1 calc R . .
C11 C 0.10539(14) 0.93635(15) 0.24623(13) 0.0271(4) Uani 1 1 d . . .
H11 H 0.1723 0.9485 0.2213 0.032 Uiso 1 1 calc R . .
C12 C 0.06431(14) 0.80621(14) 0.23021(13) 0.0227(3) Uani 1 1 d . . .
C13 C 0.11991(14) 0.69617(14) 0.17788(13) 0.0255(4) Uani 1 1 d . . .
H13 H 0.1884 0.7070 0.1543 0.031 Uiso 1 1 calc R . .
C14 C 0.07558(14) 0.57169(15) 0.16039(13) 0.0247(4) Uani 1 1 d . . .
H14 H 0.1129 0.4995 0.1229 0.030 Uiso 1 1 calc R . .
C15 C -0.09261(13) 0.90126(14) 0.32769(13) 0.0211(3) Uani 1 1 d . . .
C16 C -0.03716(13) 0.78849(14) 0.26988(13) 0.0210(3) Uani 1 1 d . . .
C17 C 0.03834(14) 0.34455(14) 0.19642(14) 0.0231(4) Uani 1 1 d . . .
C18 C 0.03923(15) 0.23037(14) 0.09273(14) 0.0258(4) Uani 1 1 d . . .
H18 H -0.0310 0.1999 0.0138 0.031 Uiso 1 1 calc R . .
C19 C 0.14234(15) 0.16148(14) 0.10469(14) 0.0259(4) Uani 1 1 d . . .
H19 H 0.1403 0.0851 0.0339 0.031 Uiso 1 1 calc R . .
C20 C 0.24976(14) 0.20442(14) 0.22142(14) 0.0237(3) Uani 1 1 d . . .
C21 C 0.35839(15) 0.13494(15) 0.23802(15) 0.0292(4) Uani 1 1 d . . .
H21 H 0.3610 0.0612 0.1677 0.035 Uiso 1 1 calc R . .
C22 C 0.45661(15) 0.17422(16) 0.35317(15) 0.0313(4) Uani 1 1 d . . .
H22 H 0.5250 0.1262 0.3607 0.038 Uiso 1 1 calc R . .
C23 C 0.45869(14) 0.28814(15) 0.46462(14) 0.0268(4) Uani 1 1 d . . .
C24 C 0.55872(15) 0.33052(17) 0.58594(15) 0.0335(4) Uani 1 1 d . . .
H24 H 0.6271 0.2829 0.5962 0.040 Uiso 1 1 calc R . .
C25 C 0.55769(16) 0.44170(17) 0.69049(16) 0.0346(4) Uani 1 1 d . . .
H25 H 0.6254 0.4683 0.7701 0.042 Uiso 1 1 calc R . .
C26 C 0.45679(15) 0.51414(15) 0.67811(15) 0.0298(4) Uani 1 1 d . . .
H26 H 0.4577 0.5893 0.7493 0.036 Uiso 1 1 calc R . .
C27 C 0.35388(14) 0.47525(14) 0.55979(14) 0.0251(4) Uani 1 1 d . . .
C28 C 0.24407(15) 0.54370(14) 0.54364(14) 0.0270(4) Uani 1 1 d . . .
H28 H 0.2426 0.6183 0.6140 0.032 Uiso 1 1 calc R . .
C29 C 0.14311(15) 0.50271(14) 0.42922(14) 0.0255(4) Uani 1 1 d . . .
H29 H 0.0729 0.5485 0.4228 0.031 Uiso 1 1 calc R . .
C30 C 0.14177(14) 0.38983(13) 0.31709(13) 0.0217(3) Uani 1 1 d . . .
C31 C 0.24890(14) 0.31953(14) 0.32945(13) 0.0217(3) Uani 1 1 d . . .
C32 C 0.35452(14) 0.36144(14) 0.45122(14) 0.0231(3) Uani 1 1 d . . .
C33 C -0.19960(14) 0.35417(14) 0.11239(13) 0.0227(4) Uani 1 1 d . . .
C34 C -0.29385(14) 0.39522(15) 0.03496(13) 0.0266(4) Uani 1 1 d . . .
H34 H -0.2674 0.4641 0.0215 0.032 Uiso 1 1 calc R . .
C35 C -0.42684(15) 0.33441(15) -0.02231(14) 0.0290(4) Uani 1 1 d . . .
H35 H -0.4882 0.3640 -0.0732 0.035 Uiso 1 1 calc R . .
C36 C -0.47110(15) 0.23071(15) -0.00593(14) 0.0293(4) Uani 1 1 d . . .
C37 C -0.37528(15) 0.18759(15) 0.06843(14) 0.0301(4) Uani 1 1 d . . .
H37 H -0.4015 0.1165 0.0793 0.036 Uiso 1 1 calc R . .
C38 C -0.24205(15) 0.24738(14) 0.12669(14) 0.0266(4) Uani 1 1 d . . .
H38 H -0.1805 0.2161 0.1757 0.032 Uiso 1 1 calc R . .
C39 C -0.61671(16) 0.16972(18) -0.06342(16) 0.0436(5) Uani 1 1 d . . .
H39A H -0.6369 0.0885 -0.1414 0.065 Uiso 1 1 calc R . .
H39B H -0.6689 0.2323 -0.0804 0.065 Uiso 1 1 calc R . .
H39C H -0.6371 0.1495 -0.0051 0.065 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C33 1.4205(19) . ?
N1 C1 1.4283(17) . ?
N1 C17 1.4358(18) . ?
C1 C14 1.395(2) . ?
C1 C2 1.413(2) . ?
C2 C16 1.424(2) . ?
C2 C3 1.437(2) . ?
C3 C4 1.350(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.429(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(2) . ?
C5 C15 1.421(2) . ?
C6 C7 1.383(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.397(2) . ?
C8 H8 0.9300 . ?
C9 C15 1.4227(19) . ?
C9 C10 1.435(2) . ?
C10 C11 1.337(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.434(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(2) . ?
C12 C16 1.4234(19) . ?
C13 C14 1.376(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.430(2) . ?
C17 C30 1.405(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.378(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(2) . ?
C19 H19 0.9300 . ?
C20 C31 1.426(2) . ?
C20 C21 1.434(2) . ?
C21 C22 1.345(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.434(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.400(2) . ?
C23 C32 1.420(2) . ?
C24 C25 1.380(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.394(2) . ?
C26 H26 0.9300 . ?
C27 C32 1.422(2) . ?
C27 C28 1.437(2) . ?
C28 C29 1.349(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.436(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.423(2) . ?
C31 C32 1.430(2) . ?
C33 C34 1.391(2) . ?
C33 C38 1.393(2) . ?
C34 C35 1.385(2) . ?
C34 H34 0.9300 . ?
C35 C36 1.386(2) . ?
C35 H35 0.9300 . ?
C36 C37 1.392(2) . ?
C36 C39 1.507(2) . ?
C37 C38 1.384(2) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

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
C33 N1 C1 121.22(11) . . ?
C33 N1 C17 119.44(11) . . ?
C1 N1 C17 116.17(11) . . ?
C14 C1 C2 119.75(13) . . ?
C14 C1 N1 119.16(13) . . ?
C2 C1 N1 121.04(12) . . ?
C1 C2 C16 118.46(13) . . ?
C1 C2 C3 123.48(13) . . ?
C16 C2 C3 118.03(13) . . ?
C4 C3 C2 121.63(14) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 121.88(14) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C15 118.90(13) . . ?
C6 C5 C4 122.95(13) . . ?
C15 C5 C4 118.15(13) . . ?
C5 C6 C7 120.84(14) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.65(14) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.96(14) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C15 118.86(13) . . ?
C8 C9 C10 122.26(14) . . ?
C15 C9 C10 118.85(14) . . ?
C11 C10 C9 121.15(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.86(14) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 122.78(13) . . ?
C13 C12 C16 118.38(13) . . ?
C11 C12 C16 118.84(14) . . ?
C14 C13 C12 121.34(14) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C1 121.30(14) . . ?
C13 C14 H14 119.4 . . ?
C1 C14 H14 119.4 . . ?
C16 C15 C5 120.28(13) . . ?
C16 C15 C9 119.92(13) . . ?
C5 C15 C9 119.80(13) . . ?
C2 C16 C15 119.99(13) . . ?
C2 C16 C12 120.67(13) . . ?
C15 C16 C12 119.31(13) . . ?
C30 C17 C18 120.18(14) . . ?
C30 C17 N1 119.15(13) . . ?
C18 C17 N1 120.60(13) . . ?
C19 C18 C17 121.19(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 121.07(14) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C31 118.46(14) . . ?
C19 C20 C21 122.77(14) . . ?
C31 C20 C21 118.73(14) . . ?
C22 C21 C20 121.37(15) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 121.75(15) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C32 118.52(15) . . ?
C24 C23 C22 123.06(15) . . ?
C32 C23 C22 118.42(14) . . ?
C23 C24 C25 121.17(15) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C26 C25 C24 120.66(15) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.50(15) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C32 C27 C26 119.31(14) . . ?
C32 C27 C28 118.35(14) . . ?
C26 C27 C28 122.31(14) . . ?
C29 C28 C27 121.76(14) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C30 121.41(14) . . ?
C28 C29 H29 119.3 . . ?
C30 C29 H29 119.3 . . ?
C17 C30 C31 118.69(13) . . ?
C17 C30 C29 122.91(14) . . ?
C31 C30 C29 118.39(13) . . ?
C20 C31 C30 120.35(13) . . ?
C20 C31 C32 119.49(14) . . ?
C30 C31 C32 120.13(13) . . ?
C27 C32 C23 119.84(14) . . ?
C27 C32 C31 119.94(14) . . ?
C23 C32 C31 120.21(14) . . ?
C34 C33 C38 118.14(13) . . ?
C34 C33 N1 122.09(13) . . ?
C38 C33 N1 119.70(13) . . ?
C33 C34 C35 120.60(14) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C36 121.87(14) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C37 C36 C35 116.99(14) . . ?
C37 C36 C39 121.51(14) . . ?
C35 C36 C39 121.48(14) . . ?
C38 C37 C36 121.92(14) . . ?
C38 C37 H37 119.0 . . ?
C36 C37 H37 119.0 . . ?
C37 C38 C33 120.41(14) . . ?
C37 C38 H38 119.8 . . ?
C33 C38 H38 119.8 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.091
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1056682'
_audit_update_record             
;
2015-03-28 deposited with the CCDC.
2016-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H25 N O'
_chemical_formula_sum            'C39 H25 N O'
_chemical_formula_weight         523.60

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'
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'
H H 0.0000 0.0000 '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                   10.920(2)
_cell_length_b                   11.212(2)
_cell_length_c                   12.802(3)
_cell_angle_alpha                115.66(3)
_cell_angle_beta                 106.77(3)
_cell_angle_gamma                90.89(3)
_cell_volume                     1334.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3545
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.23

_exptl_crystal_description       Strip
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9866
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10926
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_sigmaI/netI    0.0954
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4641
_reflns_number_gt                3521
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_reduction        SAINT-Plus
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material  XP

_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)+(0.1101P)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    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.78(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4641
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1645
_refine_ls_wR_factor_gt          0.1570
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.04058(13) 0.42406(13) 0.19154(13) 0.0241(4) Uani 1 1 d . . .
O1 O -0.54949(12) 0.14812(14) -0.02766(13) 0.0490(4) Uani 1 1 d . . .
C1 C -0.00567(15) 0.55348(17) 0.20298(15) 0.0233(4) Uani 1 1 d . . .
C2 C -0.06314(15) 0.66315(16) 0.26433(15) 0.0219(4) Uani 1 1 d . . .
C3 C -0.15708(15) 0.65580(17) 0.32181(15) 0.0237(4) Uani 1 1 d . . .
H3 H -0.1823 0.5745 0.3189 0.028 Uiso 1 1 calc R . .
C4 C -0.20903(16) 0.76259(17) 0.37916(16) 0.0258(4) Uani 1 1 d . . .
H4 H -0.2690 0.7533 0.4151 0.031 Uiso 1 1 calc R . .
C5 C -0.17506(15) 0.89040(17) 0.38677(15) 0.0243(4) Uani 1 1 d . . .
C6 C -0.22728(16) 1.00340(17) 0.44643(16) 0.0271(4) Uani 1 1 d . . .
H6 H -0.2888 0.9963 0.4817 0.032 Uiso 1 1 calc R . .
C7 C -0.18890(16) 1.12588(18) 0.45389(17) 0.0302(5) Uani 1 1 d . . .
H7 H -0.2242 1.2002 0.4946 0.036 Uiso 1 1 calc R . .
C8 C -0.09871(16) 1.13844(17) 0.40137(16) 0.0279(4) Uani 1 1 d . . .
H8 H -0.0745 1.2212 0.4065 0.034 Uiso 1 1 calc R . .
C9 C -0.04319(16) 1.02922(17) 0.34073(15) 0.0243(4) Uani 1 1 d . . .
C10 C 0.05324(16) 1.03938(18) 0.28732(16) 0.0284(4) Uani 1 1 d . . .
H10 H 0.0772 1.1209 0.2900 0.034 Uiso 1 1 calc R . .
C11 C 0.10891(17) 0.93557(18) 0.23429(16) 0.0293(5) Uani 1 1 d . . .
H11 H 0.1727 0.9467 0.2028 0.035 Uiso 1 1 calc R . .
C12 C 0.07290(16) 0.80656(17) 0.22442(15) 0.0244(4) Uani 1 1 d . . .
C13 C 0.13035(16) 0.69620(18) 0.16954(16) 0.0281(4) Uani 1 1 d . . .
H13 H 0.1964 0.7062 0.1401 0.034 Uiso 1 1 calc R . .
C14 C 0.09091(16) 0.57278(18) 0.15820(16) 0.0270(4) Uani 1 1 d . . .
H14 H 0.1297 0.5005 0.1197 0.032 Uiso 1 1 calc R . .
C15 C -0.02511(15) 0.78987(17) 0.27230(15) 0.0213(4) Uani 1 1 d . . .
C16 C -0.08121(15) 0.90275(16) 0.33310(15) 0.0222(4) Uani 1 1 d . . .
C17 C 0.06351(16) 0.34969(17) 0.20513(16) 0.0244(4) Uani 1 1 d . . .
C18 C 0.07467(17) 0.23833(17) 0.10389(16) 0.0280(4) Uani 1 1 d . . .
H18 H 0.0113 0.2093 0.0277 0.034 Uiso 1 1 calc R . .
C19 C 0.17832(16) 0.17074(17) 0.11526(16) 0.0287(4) Uani 1 1 d . . .
H19 H 0.1838 0.0969 0.0465 0.034 Uiso 1 1 calc R . .
C20 C 0.27498(16) 0.21129(17) 0.22812(16) 0.0262(4) Uani 1 1 d . . .
C21 C 0.38382(17) 0.14280(18) 0.24483(18) 0.0328(5) Uani 1 1 d . . .
H21 H 0.3939 0.0714 0.1768 0.039 Uiso 1 1 calc R . .
C22 C 0.46969(17) 0.17863(19) 0.35414(18) 0.0332(5) Uani 1 1 d . . .
H22 H 0.5377 0.1305 0.3609 0.040 Uiso 1 1 calc R . .
C23 C 0.46174(16) 0.28962(18) 0.46323(17) 0.0289(4) Uani 1 1 d . . .
C24 C 0.55057(17) 0.3290(2) 0.58072(18) 0.0347(5) Uani 1 1 d . . .
H24 H 0.6177 0.2808 0.5909 0.042 Uiso 1 1 calc R . .
C25 C 0.53964(18) 0.4387(2) 0.68176(18) 0.0358(5) Uani 1 1 d . . .
H25 H 0.6001 0.4637 0.7587 0.043 Uiso 1 1 calc R . .
C26 C 0.44025(17) 0.51146(18) 0.66985(17) 0.0308(5) Uani 1 1 d . . .
H26 H 0.4350 0.5855 0.7386 0.037 Uiso 1 1 calc R . .
C27 C 0.34751(16) 0.47483(17) 0.55541(16) 0.0260(4) Uani 1 1 d . . .
C28 C 0.23946(16) 0.54289(17) 0.53993(16) 0.0267(4) Uani 1 1 d . . .
H28 H 0.2320 0.6163 0.6080 0.032 Uiso 1 1 calc R . .
C29 C 0.14850(16) 0.50444(16) 0.43063(16) 0.0257(4) Uani 1 1 d . . .
H29 H 0.0787 0.5504 0.4249 0.031 Uiso 1 1 calc R . .
C30 C 0.15680(15) 0.39261(16) 0.32121(15) 0.0228(4) Uani 1 1 d . . .
C31 C 0.26335(16) 0.32330(16) 0.33288(15) 0.0230(4) Uani 1 1 d . . .
C32 C 0.35838(16) 0.36319(17) 0.45071(16) 0.0239(4) Uani 1 1 d . . .
C33 C -0.16991(15) 0.35467(16) 0.13109(15) 0.0239(4) Uani 1 1 d . . .
C34 C -0.20523(17) 0.24042(17) 0.14049(16) 0.0286(4) Uani 1 1 d . . .
H34 H -0.1427 0.2088 0.1843 0.034 Uiso 1 1 calc R . .
C35 C -0.33121(17) 0.17365(19) 0.08604(17) 0.0330(5) Uani 1 1 d . . .
H35 H -0.3525 0.0972 0.0928 0.040 Uiso 1 1 calc R . .
C36 C -0.42667(17) 0.21981(19) 0.02109(17) 0.0334(5) Uani 1 1 d . . .
C37 C -0.39358(17) 0.33300(18) 0.00996(16) 0.0311(5) Uani 1 1 d . . .
H37 H -0.4564 0.3645 -0.0337 0.037 Uiso 1 1 calc R . .
C38 C -0.26565(16) 0.39909(17) 0.06463(15) 0.0270(4) Uani 1 1 d . . .
H38 H -0.2439 0.4744 0.0565 0.032 Uiso 1 1 calc R . .
C39 C -0.6504(2) 0.1999(3) -0.0845(3) 0.0868(11) Uani 1 1 d . . .
H39A H -0.6497 0.2911 -0.0285 0.130 Uiso 1 1 calc R . .
H39B H -0.7322 0.1470 -0.1068 0.130 Uiso 1 1 calc R . .
H39C H -0.6376 0.1967 -0.1567 0.130 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C33 1.419(2) . ?
N1 C1 1.428(2) . ?
N1 C17 1.435(2) . ?
O1 C36 1.372(2) . ?
O1 C39 1.415(3) . ?
C1 C14 1.392(2) . ?
C1 C2 1.412(2) . ?
C2 C15 1.426(2) . ?
C2 C3 1.444(2) . ?
C3 C4 1.340(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.429(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 C16 1.423(2) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(2) . ?
C8 H8 0.9300 . ?
C9 C16 1.425(2) . ?
C9 C10 1.438(2) . ?
C10 C11 1.327(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.435(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(2) . ?
C12 C15 1.424(2) . ?
C13 C14 1.376(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.424(2) . ?
C17 C18 1.396(2) . ?
C17 C30 1.403(2) . ?
C18 C19 1.380(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(2) . ?
C19 H19 0.9300 . ?
C20 C31 1.427(2) . ?
C20 C21 1.439(2) . ?
C21 C22 1.320(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.440(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.403(3) . ?
C23 C32 1.421(2) . ?
C24 C25 1.384(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.397(3) . ?
C26 H26 0.9300 . ?
C27 C32 1.422(2) . ?
C27 C28 1.427(2) . ?
C28 C29 1.339(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.449(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.417(2) . ?
C31 C32 1.432(2) . ?
C33 C38 1.391(2) . ?
C33 C34 1.396(2) . ?
C34 C35 1.379(2) . ?
C34 H34 0.9300 . ?
C35 C36 1.391(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.390(3) . ?
C37 C38 1.395(2) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?

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
C33 N1 C1 121.68(13) . . ?
C33 N1 C17 119.17(13) . . ?
C1 N1 C17 115.91(13) . . ?
C36 O1 C39 117.19(16) . . ?
C14 C1 C2 119.74(15) . . ?
C14 C1 N1 119.28(15) . . ?
C2 C1 N1 120.90(14) . . ?
C1 C2 C15 118.45(15) . . ?
C1 C2 C3 124.01(15) . . ?
C15 C2 C3 117.53(15) . . ?
C4 C3 C2 121.97(15) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C5 121.98(16) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C16 118.90(15) . . ?
C6 C5 C4 123.13(15) . . ?
C16 C5 C4 117.95(15) . . ?
C7 C6 C5 120.97(16) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.48(16) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.13(15) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C16 118.96(15) . . ?
C8 C9 C10 122.61(15) . . ?
C16 C9 C10 118.41(15) . . ?
C11 C10 C9 121.77(15) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 121.44(16) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C15 118.44(15) . . ?
C13 C12 C11 122.47(15) . . ?
C15 C12 C11 119.09(16) . . ?
C14 C13 C12 121.06(15) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C1 121.60(16) . . ?
C13 C14 H14 119.2 . . ?
C1 C14 H14 119.2 . . ?
C16 C15 C12 119.25(15) . . ?
C16 C15 C2 120.10(15) . . ?
C12 C15 C2 120.60(16) . . ?
C5 C16 C15 120.47(15) . . ?
C5 C16 C9 119.56(15) . . ?
C15 C16 C9 119.97(15) . . ?
C18 C17 C30 120.08(16) . . ?
C18 C17 N1 120.71(16) . . ?
C30 C17 N1 119.18(15) . . ?
C19 C18 C17 120.95(17) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 121.11(17) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C31 118.51(16) . . ?
C19 C20 C21 123.10(17) . . ?
C31 C20 C21 118.35(17) . . ?
C22 C21 C20 121.73(18) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C21 C22 C23 122.28(17) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
C24 C23 C32 118.40(17) . . ?
C24 C23 C22 123.57(17) . . ?
C32 C23 C22 118.03(17) . . ?
C25 C24 C23 120.90(17) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.92(18) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 120.56(18) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C32 119.07(16) . . ?
C26 C27 C28 122.41(17) . . ?
C32 C27 C28 118.49(16) . . ?
C29 C28 C27 122.12(17) . . ?
C29 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
C28 C29 C30 121.25(16) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C17 C30 C31 118.97(16) . . ?
C17 C30 C29 122.83(15) . . ?
C31 C30 C29 118.21(16) . . ?
C30 C31 C20 120.36(16) . . ?
C30 C31 C32 120.09(16) . . ?
C20 C31 C32 119.54(16) . . ?
C23 C32 C27 120.14(17) . . ?
C23 C32 C31 120.02(16) . . ?
C27 C32 C31 119.82(16) . . ?
C38 C33 C34 117.98(16) . . ?
C38 C33 N1 122.01(14) . . ?
C34 C33 N1 119.98(15) . . ?
C35 C34 C33 121.17(16) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C34 C35 C36 120.45(17) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
O1 C36 C37 124.53(17) . . ?
O1 C36 C35 116.09(16) . . ?
C37 C36 C35 119.38(17) . . ?
C36 C37 C38 119.65(16) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C33 C38 C37 121.36(16) . . ?
C33 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
O1 C39 H39A 109.5 . . ?
O1 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O1 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.119
