# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1526254'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-10-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N O3'
_chemical_formula_sum            'C27 H21 N O3'
_chemical_formula_weight         407.45

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           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_HALL  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   37.951(3)
_cell_length_b                   24.115(2)
_cell_length_c                   9.5003(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8694.4(11)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3044
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      25.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3424
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Sapphire3'
_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            25627
_diffrn_reflns_av_R_equivalents  0.1343
_diffrn_reflns_av_sigmaI/netI    0.0782
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3819
_reflns_number_gt                2741
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0684P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   2(2)
_refine_ls_number_reflns         3819
_refine_ls_number_parameters     280
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0660
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O001 O 0.12138(7) 0.05651(12) 0.2223(3) 0.0622(7) Uani 1 1 d . . .
O002 O 0.13871(7) -0.02819(12) 0.2896(3) 0.0683(8) Uani 1 1 d . . .
C16 C 0.09390(8) 0.01592(14) 0.4226(4) 0.0422(8) Uani 1 1 d . . .
C9 C 0.04315(9) 0.06806(14) 0.4948(4) 0.0429(8) Uani 1 1 d . . .
N1 N 0.08993(9) -0.08242(15) 0.5371(4) 0.0654(9) Uani 1 1 d . . .
O1 O 0.17855(7) 0.04626(14) 0.5163(3) 0.0796(9) Uani 1 1 d . . .
C6 C 0.04999(9) -0.00900(16) 0.1359(4) 0.0463(9) Uani 1 1 d . . .
C7 C 0.04011(9) 0.02544(14) 0.2568(4) 0.0448(9) Uani 1 1 d . . .
H008 H 0.0189 0.0443 0.2466 0.054 Uiso 1 1 calc R . .
C21 C 0.16548(10) 0.02597(15) 0.6214(4) 0.0493(9) Uani 1 1 d . . .
C8 C 0.05653(8) 0.03422(14) 0.3792(4) 0.0423(8) Uani 1 1 d . . .
C14 C 0.06996(9) 0.08250(14) 0.5872(4) 0.0448(9) Uani 1 1 d . . .
C19 C 0.09189(9) -0.04020(18) 0.4858(4) 0.0481(9) Uani 1 1 d . . .
C17 C 0.11963(10) 0.01703(18) 0.2992(4) 0.0518(9) Uani 1 1 d . . .
C22 C 0.18679(10) -0.00894(15) 0.7175(4) 0.0475(9) Uani 1 1 d . . .
C15 C 0.10511(9) 0.05933(15) 0.5386(4) 0.0468(9) Uani 1 1 d . . .
H015 H 0.1181 0.0893 0.4918 0.056 Uiso 1 1 calc R . .
C20 C 0.12788(9) 0.03761(16) 0.6585(4) 0.0484(9) Uani 1 1 d . . .
H01A H 0.1275 0.0645 0.7343 0.058 Uiso 1 1 calc R . .
H01B H 0.1174 0.0037 0.6939 0.058 Uiso 1 1 calc R . .
C10 C 0.00868(10) 0.08570(16) 0.5187(5) 0.0559(10) Uani 1 1 d . . .
H017 H -0.0094 0.0758 0.4575 0.067 Uiso 1 1 calc R . .
C5 C 0.04372(11) 0.00995(18) 0.0008(4) 0.0606(11) Uani 1 1 d . . .
H018 H 0.0337 0.0448 -0.0122 0.073 Uiso 1 1 calc R . .
C27 C 0.17244(10) -0.05443(17) 0.7870(4) 0.0560(10) Uani 1 1 d . . .
H019 H 0.1486 -0.0626 0.7768 0.067 Uiso 1 1 calc R . .
C2 C 0.07119(11) -0.09389(18) 0.0353(5) 0.0656(12) Uani 1 1 d . . .
H020 H 0.0804 -0.1293 0.0476 0.079 Uiso 1 1 calc R . .
C13 C 0.06312(10) 0.11501(16) 0.7029(4) 0.0574(10) Uani 1 1 d . . .
H021 H 0.0811 0.1250 0.7643 0.069 Uiso 1 1 calc R . .
C1 C 0.06322(10) -0.06210(18) 0.1504(4) 0.0573(10) Uani 1 1 d . . .
H022 H 0.0668 -0.0765 0.2400 0.069 Uiso 1 1 calc R . .
C23 C 0.22218(10) 0.00250(17) 0.7358(5) 0.0626(11) Uani 1 1 d . . .
H023 H 0.2324 0.0319 0.6874 0.075 Uiso 1 1 calc R . .
C11 C 0.00208(11) 0.11814(17) 0.6351(5) 0.0630(11) Uani 1 1 d . . .
H024 H -0.0207 0.1305 0.6526 0.076 Uiso 1 1 calc R . .
C3 C 0.06576(11) -0.0740(2) -0.0969(5) 0.0708(13) Uani 1 1 d . . .
H025 H 0.0713 -0.0957 -0.1748 0.085 Uiso 1 1 calc R . .
C26 C 0.19355(12) -0.08767(18) 0.8715(5) 0.0707(12) Uani 1 1 d . . .
H026 H 0.1842 -0.1189 0.9152 0.085 Uiso 1 1 calc R . .
C12 C 0.02890(11) 0.13254(18) 0.7260(5) 0.0660(12) Uani 1 1 d . . .
H027 H 0.0239 0.1544 0.8042 0.079 Uiso 1 1 calc R . .
C24 C 0.24235(12) -0.0290(2) 0.8245(5) 0.0755(14) Uani 1 1 d . . .
H028 H 0.2658 -0.0196 0.8399 0.091 Uiso 1 1 calc R . .
C4 C 0.05210(12) -0.0219(2) -0.1148(5) 0.0755(13) Uani 1 1 d . . .
H029 H 0.0485 -0.0080 -0.2049 0.091 Uiso 1 1 calc R . .
C25 C 0.22850(13) -0.0737(2) 0.8899(5) 0.0776(14) Uani 1 1 d . . .
H030 H 0.2427 -0.0953 0.9479 0.093 Uiso 1 1 calc R . .
C18 C 0.16297(16) -0.0294(3) 0.1696(6) 0.121(2) Uani 1 1 d . . .
H03A H 0.1761 -0.0634 0.1707 0.182 Uiso 1 1 calc R . .
H03B H 0.1789 0.0014 0.1759 0.182 Uiso 1 1 calc R . .
H03C H 0.1498 -0.0269 0.0836 0.182 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
O001 C17 1.202(5) . ?
O002 C17 1.312(5) . ?
O002 C18 1.465(5) . ?
C16 C19 1.483(6) . ?
C16 C17 1.526(5) . ?
C16 C8 1.542(4) . ?
C16 C15 1.578(5) . ?
C9 C14 1.388(5) . ?
C9 C10 1.394(5) . ?
C9 C8 1.460(5) . ?
N1 C19 1.131(5) . ?
O1 C21 1.217(5) . ?
C6 C1 1.382(5) . ?
C6 C5 1.383(5) . ?
C6 C7 1.466(5) . ?
C7 C8 1.336(5) . ?
C21 C22 1.483(5) . ?
C21 C20 1.497(5) . ?
C14 C13 1.375(5) . ?
C14 C15 1.518(5) . ?
C22 C23 1.382(5) . ?
C22 C27 1.391(5) . ?
C15 C20 1.523(5) . ?
C10 C11 1.378(6) . ?
C5 C4 1.377(6) . ?
C27 C26 1.389(5) . ?
C2 C3 1.360(6) . ?
C2 C1 1.369(6) . ?
C13 C12 1.383(5) . ?
C23 C24 1.369(6) . ?
C11 C12 1.379(6) . ?
C3 C4 1.370(7) . ?
C26 C25 1.379(6) . ?
C24 C25 1.350(6) . ?

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
C17 O002 C18 114.6(4) . . ?
C19 C16 C17 111.1(3) . . ?
C19 C16 C8 108.8(3) . . ?
C17 C16 C8 112.2(3) . . ?
C19 C16 C15 109.7(3) . . ?
C17 C16 C15 110.6(3) . . ?
C8 C16 C15 104.2(3) . . ?
C14 C9 C10 120.6(3) . . ?
C14 C9 C8 111.2(3) . . ?
C10 C9 C8 128.3(3) . . ?
C1 C6 C5 117.4(4) . . ?
C1 C6 C7 122.7(4) . . ?
C5 C6 C7 119.7(4) . . ?
C8 C7 C6 130.7(3) . . ?
O1 C21 C22 120.8(4) . . ?
O1 C21 C20 120.4(4) . . ?
C22 C21 C20 118.8(3) . . ?
C7 C8 C9 125.5(3) . . ?
C7 C8 C16 128.1(3) . . ?
C9 C8 C16 106.2(3) . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 C15 128.2(3) . . ?
C9 C14 C15 111.1(3) . . ?
N1 C19 C16 178.2(4) . . ?
O001 C17 O002 125.9(4) . . ?
O001 C17 C16 121.1(4) . . ?
O002 C17 C16 113.1(3) . . ?
C23 C22 C27 118.6(4) . . ?
C23 C22 C21 119.6(3) . . ?
C27 C22 C21 121.8(3) . . ?
C14 C15 C20 113.4(3) . . ?
C14 C15 C16 102.7(3) . . ?
C20 C15 C16 116.5(3) . . ?
C21 C20 C15 115.4(3) . . ?
C11 C10 C9 118.3(4) . . ?
C4 C5 C6 121.1(4) . . ?
C26 C27 C22 120.2(4) . . ?
C3 C2 C1 120.4(4) . . ?
C14 C13 C12 118.6(4) . . ?
C2 C1 C6 121.3(4) . . ?
C24 C23 C22 120.7(4) . . ?
C10 C11 C12 120.8(4) . . ?
C2 C3 C4 119.6(4) . . ?
C25 C26 C27 119.1(4) . . ?
C11 C12 C13 121.1(4) . . ?
C25 C24 C23 120.5(4) . . ?
C3 C4 C5 120.0(4) . . ?
C24 C25 C26 120.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.038
