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

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

data_a
_database_code_depnum_ccdc_archive 'CCDC 1586761'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 N O2'
_chemical_formula_weight         453.51

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'

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

_cell_length_a                   8.1795(14)
_cell_length_b                   11.924(7)
_cell_length_c                   14.235(2)
_cell_angle_alpha                108.1050(16)
_cell_angle_beta                 96.2450(16)
_cell_angle_gamma                108.7120(15)
_cell_volume                     1215.9(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      12

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9773
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_process_details   '(XCAD4; Harms & Wocadlo, 1995)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7300
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4227
_reflns_number_gt                2640
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0400P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4227
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1145
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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 0.28691(19) 0.91982(14) 0.55823(10) 0.0464(4) Uani 1 1 d . . .
O2 O 0.38835(18) 0.76262(14) 0.78285(11) 0.0669(4) Uani 1 1 d . . .
C10 C 0.3767(2) 1.03982(17) 0.63293(13) 0.0435(5) Uani 1 1 d . . .
C1 C 0.3206(2) 0.83053(17) 0.58921(13) 0.0444(5) Uani 1 1 d . . .
C25 C 0.4309(2) 0.89232(17) 0.68550(13) 0.0416(4) Uani 1 1 d . . .
C26 C 0.4947(3) 0.83248(18) 0.75184(13) 0.0464(5) Uani 1 1 d . . .
C27 C 0.6875(2) 0.85896(16) 0.77860(13) 0.0441(5) Uani 1 1 d . . .
C24 C 0.4687(2) 1.02418(17) 0.71313(13) 0.0420(4) Uani 1 1 d . . .
O1 O 0.3438(2) 1.15719(14) 0.53209(11) 0.0795(5) Uani 1 1 d . . .
C23 C 0.5914(2) 1.12433(17) 0.80798(14) 0.0449(5) Uani 1 1 d . . .
C2 C 0.2516(2) 0.69749(18) 0.51894(14) 0.0510(5) Uani 1 1 d . . .
C12 C 0.3818(3) 1.26526(19) 0.70603(16) 0.0556(5) Uani 1 1 d . . .
C11 C 0.3671(3) 1.15402(19) 0.61770(15) 0.0528(5) Uani 1 1 d . . .
C28 C 0.7953(3) 0.89181(18) 0.71521(15) 0.0556(5) Uani 1 1 d . . .
H28 H 0.7493 0.9033 0.6578 0.067 Uiso 1 1 calc R . .
C9 C 0.1746(3) 0.8871(2) 0.45874(14) 0.0604(6) Uani 1 1 d . . .
H9A H 0.2466 0.8903 0.4091 0.072 Uiso 1 1 calc R . .
H9B H 0.1181 0.9480 0.4626 0.072 Uiso 1 1 calc R . .
C22 C 0.5787(3) 1.11559(19) 0.90165(14) 0.0569(5) Uani 1 1 d . . .
H22 H 0.4893 1.0464 0.9053 0.068 Uiso 1 1 calc R . .
C18 C 0.7260(3) 1.22930(19) 0.80587(16) 0.0613(6) Uani 1 1 d . . .
H18 H 0.7376 1.2383 0.7441 0.074 Uiso 1 1 calc R . .
C32 C 0.7577(3) 0.84341(19) 0.86437(15) 0.0633(6) Uani 1 1 d . . .
H32 H 0.6853 0.8205 0.9067 0.076 Uiso 1 1 calc R . .
C3 C 0.3226(3) 0.60971(19) 0.53157(16) 0.0630(6) Uani 1 1 d . . .
H3 H 0.4161 0.6349 0.5866 0.076 Uiso 1 1 calc R . .
C7 C 0.1130(3) 0.6594(2) 0.43591(16) 0.0615(6) Uani 1 1 d . . .
C17 C 0.3134(3) 1.2545(2) 0.78889(16) 0.0651(6) Uani 1 1 d . . .
H17 H 0.2620 1.1746 0.7925 0.078 Uiso 1 1 calc R . .
C21 C 0.6957(4) 1.2073(2) 0.98976(16) 0.0755(7) Uani 1 1 d . . .
H21 H 0.6840 1.1996 1.0519 0.091 Uiso 1 1 calc R . .
C30 C 1.0398(3) 0.8923(2) 0.8234(2) 0.0851(8) Uani 1 1 d . . .
H30 H 1.1586 0.9029 0.8382 0.102 Uiso 1 1 calc R . .
C29 C 0.9717(3) 0.9074(2) 0.7377(2) 0.0746(7) Uani 1 1 d . . .
H29 H 1.0442 0.9282 0.6948 0.090 Uiso 1 1 calc R . .
C8 C 0.0344(3) 0.7545(2) 0.42626(16) 0.0714(7) Uani 1 1 d . . .
H8A H -0.0518 0.7563 0.4679 0.086 Uiso 1 1 calc R . .
H8B H -0.0272 0.7279 0.3562 0.086 Uiso 1 1 calc R . .
C19 C 0.8433(3) 1.3207(2) 0.8947(2) 0.0827(8) Uani 1 1 d . . .
H19 H 0.9331 1.3905 0.8922 0.099 Uiso 1 1 calc R . .
C4 C 0.2544(3) 0.4853(2) 0.46268(19) 0.0786(7) Uani 1 1 d . . .
H4 H 0.3015 0.4271 0.4718 0.094 Uiso 1 1 calc R . .
C6 C 0.0469(3) 0.5335(2) 0.36705(18) 0.0831(8) Uani 1 1 d . . .
H6 H -0.0457 0.5074 0.3112 0.100 Uiso 1 1 calc R . .
C31 C 0.9346(4) 0.8618(2) 0.88727(19) 0.0820(8) Uani 1 1 d . . .
H31 H 0.9824 0.8535 0.9459 0.098 Uiso 1 1 calc R . .
C20 C 0.8280(4) 1.3090(2) 0.9865(2) 0.0870(8) Uani 1 1 d . . .
H20 H 0.9076 1.3701 1.0460 0.104 Uiso 1 1 calc R . .
C14 C 0.4652(5) 1.4904(3) 0.7790(3) 0.1244(13) Uani 1 1 d . . .
H14 H 0.5169 1.5705 0.7758 0.149 Uiso 1 1 calc R . .
C13 C 0.4577(3) 1.3855(2) 0.7022(2) 0.0843(8) Uani 1 1 d . . .
H13 H 0.5036 1.3943 0.6468 0.101 Uiso 1 1 calc R . .
C5 C 0.1173(4) 0.4482(2) 0.3811(2) 0.0896(8) Uani 1 1 d . . .
H5 H 0.0718 0.3646 0.3349 0.107 Uiso 1 1 calc R . .
C15 C 0.3973(5) 1.4793(3) 0.8610(3) 0.1213(13) Uani 1 1 d . . .
H15 H 0.4030 1.5516 0.9132 0.146 Uiso 1 1 calc R . .
C16 C 0.3208(4) 1.3611(3) 0.86618(19) 0.0977(9) Uani 1 1 d . . .
H16 H 0.2742 1.3532 0.9216 0.117 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 C1 1.363(2) . ?
N1 C10 1.388(2) . ?
N1 C9 1.465(2) . ?
O2 C26 1.222(2) . ?
C10 C24 1.393(2) . ?
C10 C11 1.468(3) . ?
C1 C25 1.383(2) . ?
C1 C2 1.467(3) . ?
C25 C24 1.414(2) . ?
C25 C26 1.491(2) . ?
C26 C27 1.485(2) . ?
C27 C32 1.382(2) . ?
C27 C28 1.385(3) . ?
C24 C23 1.480(2) . ?
O1 C11 1.227(2) . ?
C23 C22 1.382(2) . ?
C23 C18 1.388(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.396(3) . ?
C12 C17 1.383(3) . ?
C12 C13 1.389(3) . ?
C12 C11 1.478(3) . ?
C28 C29 1.381(3) . ?
C9 C8 1.515(3) . ?
C22 C21 1.378(3) . ?
C18 C19 1.385(3) . ?
C32 C31 1.378(3) . ?
C3 C4 1.385(3) . ?
C7 C6 1.398(3) . ?
C7 C8 1.504(3) . ?
C17 C16 1.377(3) . ?
C21 C20 1.360(3) . ?
C30 C31 1.370(4) . ?
C30 C29 1.373(3) . ?
C19 C20 1.371(3) . ?
C4 C5 1.371(3) . ?
C6 C5 1.373(4) . ?
C14 C13 1.360(4) . ?
C14 C15 1.371(5) . ?
C15 C16 1.374(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C10 109.74(14) . . ?
C1 N1 C9 122.40(16) . . ?
C10 N1 C9 127.85(16) . . ?
N1 C10 C24 107.27(16) . . ?
N1 C10 C11 120.95(16) . . ?
C24 C10 C11 131.76(17) . . ?
N1 C1 C25 107.93(16) . . ?
N1 C1 C2 119.46(16) . . ?
C25 C1 C2 132.43(17) . . ?
C1 C25 C24 107.97(15) . . ?
C1 C25 C26 126.97(17) . . ?
C24 C25 C26 125.02(15) . . ?
O2 C26 C27 121.26(17) . . ?
O2 C26 C25 119.74(17) . . ?
C27 C26 C25 119.00(17) . . ?
C32 C27 C28 119.73(19) . . ?
C32 C27 C26 119.66(18) . . ?
C28 C27 C26 120.49(17) . . ?
C10 C24 C25 107.08(15) . . ?
C10 C24 C23 127.87(17) . . ?
C25 C24 C23 124.98(15) . . ?
C22 C23 C18 117.53(18) . . ?
C22 C23 C24 121.33(17) . . ?
C18 C23 C24 121.13(17) . . ?
C7 C2 C3 119.42(19) . . ?
C7 C2 C1 118.18(18) . . ?
C3 C2 C1 122.38(18) . . ?
C17 C12 C13 118.7(2) . . ?
C17 C12 C11 123.0(2) . . ?
C13 C12 C11 118.1(2) . . ?
O1 C11 C10 120.65(19) . . ?
O1 C11 C12 119.61(19) . . ?
C10 C11 C12 119.73(18) . . ?
C29 C28 C27 119.7(2) . . ?
N1 C9 C8 109.53(17) . . ?
C21 C22 C23 121.3(2) . . ?
C19 C18 C23 120.7(2) . . ?
C31 C32 C27 120.2(2) . . ?
C4 C3 C2 120.4(2) . . ?
C2 C7 C6 119.2(2) . . ?
C2 C7 C8 118.32(19) . . ?
C6 C7 C8 122.4(2) . . ?
C16 C17 C12 120.6(2) . . ?
C20 C21 C22 120.5(2) . . ?
C31 C30 C29 120.7(2) . . ?
C30 C29 C28 120.0(2) . . ?
C7 C8 C9 112.05(18) . . ?
C20 C19 C18 120.4(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C6 C7 120.6(2) . . ?
C30 C31 C32 119.8(2) . . ?
C21 C20 C19 119.5(2) . . ?
C13 C14 C15 120.7(3) . . ?
C14 C13 C12 120.4(3) . . ?
C4 C5 C6 120.4(2) . . ?
C14 C15 C16 119.9(3) . . ?
C15 C16 C17 119.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046
