# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_exp_chem_y-6-23
_database_code_depnum_ccdc_archive 'CCDC 1822563'
_audit_update_record             
;
2018-02-07 deposited with the CCDC.
2018-04-24 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 H31 N2 O2'
_chemical_formula_weight         475.59

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   'P 21 21 21'

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

_cell_length_a                   7.2924(4)
_cell_length_b                   14.2140(8)
_cell_length_c                   25.7900(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2673.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3124
_cell_measurement_theta_min      3.9140
_cell_measurement_theta_max      26.5500

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1012
_exptl_absorpt_coefficient_mu    0.074
_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, Eos, Gemini ultra'
_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            12519
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4687
_reflns_number_gt                3700
_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
_chemical_absolute_configuration s
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)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   2.0(19)
_refine_ls_number_reflns         4687
_refine_ls_number_parameters     327
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C15 C 0.4655(4) 0.84170(18) 0.08237(10) 0.0488(6) Uani 1 1 d . . .
C16 C 0.5819(4) 0.8992(2) 0.04949(12) 0.0611(8) Uani 1 1 d . . .
C10 C 0.2927(3) 0.84796(17) 0.06685(10) 0.0448(6) Uani 1 1 d . . .
C7 C 0.2746(3) 0.92054(17) 0.02478(10) 0.0447(6) Uani 1 1 d . . .
C9 C 0.1615(4) 1.00377(18) 0.04262(13) 0.0593(7) Uani 1 1 d . . .
H9A H 0.2059 1.0252 0.0756 0.089 Uiso 1 1 calc R . .
H9B H 0.0354 0.9852 0.0459 0.089 Uiso 1 1 calc R . .
H9C H 0.1713 1.0537 0.0177 0.089 Uiso 1 1 calc R . .
C11 C 0.1373(4) 0.7959(2) 0.09109(12) 0.0604(7) Uani 1 1 d . . .
H11A H 0.0970 0.7461 0.0680 0.073 Uiso 1 1 calc R . .
H11B H 0.0351 0.8385 0.0965 0.073 Uiso 1 1 calc R . .
C5 C 0.3443(4) 0.94061(19) -0.06449(11) 0.0602(7) Uani 1 1 d . . .
C6 C 0.4947(4) 0.97100(18) -0.03557(11) 0.0579(7) Uani 1 1 d . . .
C8 C 0.2153(4) 0.8881(2) -0.02935(10) 0.0593(7) Uani 1 1 d . . .
H8A H 0.2296 0.8206 -0.0332 0.071 Uiso 1 1 calc R . .
H8B H 0.0888 0.9050 -0.0363 0.071 Uiso 1 1 calc R . .
C4 C 0.3363(6) 0.9583(2) -0.11664(13) 0.0860(11) Uani 1 1 d . . .
H4 H 0.2343 0.9400 -0.1358 0.103 Uiso 1 1 calc R . .
C13 C 0.3810(5) 0.7110(3) 0.14100(14) 0.0830(10) Uani 1 1 d . . .
H13A H 0.3812 0.6596 0.1163 0.100 Uiso 1 1 calc R . .
H13B H 0.4086 0.6850 0.1749 0.100 Uiso 1 1 calc R . .
C14 C 0.5297(5) 0.7806(2) 0.12631(11) 0.0644(8) Uani 1 1 d . . .
H14A H 0.5598 0.8196 0.1560 0.077 Uiso 1 1 calc R . .
H14B H 0.6395 0.7469 0.1160 0.077 Uiso 1 1 calc R . .
C12 C 0.1953(5) 0.7541(3) 0.14227(14) 0.0830(10) Uani 1 1 d . . .
H12A H 0.1934 0.8030 0.1685 0.100 Uiso 1 1 calc R . .
H12B H 0.1070 0.7065 0.1524 0.100 Uiso 1 1 calc R . .
C1 C 0.6436(5) 1.0162(2) -0.05782(17) 0.0835(11) Uani 1 1 d . . .
H1 H 0.7441 1.0357 -0.0384 0.100 Uiso 1 1 calc R . .
C2 C 0.6325(8) 1.0307(3) -0.1123(2) 0.1029(15) Uani 1 1 d . . .
H2 H 0.7300 1.0593 -0.1294 0.124 Uiso 1 1 calc R . .
C3 C 0.4805(8) 1.0034(3) -0.14049(16) 0.1061(15) Uani 1 1 d . . .
H3 H 0.4755 1.0156 -0.1759 0.127 Uiso 1 1 calc R . .
N1 N 0.4677(3) 0.94924(15) 0.01725(9) 0.0522(6) Uani 1 1 d . . .
O1 O 0.7500(3) 0.9032(2) 0.04772(12) 0.0990(9) Uani 1 1 d . . .
C26 C 0.7495(4) 0.16025(16) 0.13652(10) 0.0450(6) Uani 1 1 d . . .
C25 C 0.8771(4) 0.00591(17) 0.17953(11) 0.0492(6) Uani 1 1 d . . .
H25A H 0.8641 -0.0188 0.1447 0.059 Uiso 1 1 calc R . .
H25B H 1.0060 0.0074 0.1888 0.059 Uiso 1 1 calc R . .
C32 C 0.4695(4) 0.11119(17) 0.16638(10) 0.0445(6) Uani 1 1 d . . .
C22 C 0.6020(4) -0.00582(16) 0.22792(9) 0.0440(6) Uani 1 1 d . . .
C31 C 0.5707(4) 0.16589(16) 0.12756(10) 0.0464(6) Uani 1 1 d . . .
C23 C 0.7877(3) 0.10471(16) 0.18473(9) 0.0415(6) Uani 1 1 d . . .
C24 C 0.8878(4) 0.16158(19) 0.22585(12) 0.0612(7) Uani 1 1 d . . .
H24A H 0.8203 0.2181 0.2330 0.092 Uiso 1 1 calc R . .
H24B H 1.0080 0.1776 0.2135 0.092 Uiso 1 1 calc R . .
H24C H 0.8983 0.1249 0.2570 0.092 Uiso 1 1 calc R . .
C21 C 0.7669(4) -0.05050(16) 0.21801(10) 0.0463(6) Uani 1 1 d . . .
C17 C 0.4685(4) -0.0449(2) 0.25901(11) 0.0601(7) Uani 1 1 d . . .
H17 H 0.3571 -0.0149 0.2649 0.072 Uiso 1 1 calc R . .
C20 C 0.8020(5) -0.13613(19) 0.24048(12) 0.0647(8) Uani 1 1 d . . .
H20 H 0.9120 -0.1671 0.2341 0.078 Uiso 1 1 calc R . .
C30 C 0.4831(5) 0.2199(2) 0.08451(13) 0.0788(10) Uani 1 1 d . . .
H30 H 0.3624 0.2128 0.0735 0.095 Uiso 1 1 calc R . .
C18 C 0.5097(5) -0.1320(2) 0.28116(12) 0.0726(9) Uani 1 1 d . . .
H18 H 0.4232 -0.1609 0.3023 0.087 Uiso 1 1 calc R . .
C19 C 0.6722(5) -0.1757(2) 0.27267(14) 0.0741(9) Uani 1 1 d . . .
H19 H 0.6964 -0.2330 0.2887 0.089 Uiso 1 1 calc R . .
C27 C 0.8914(5) 0.2102(2) 0.10528(13) 0.0692(9) Uani 1 1 d . . .
H27A H 0.9848 0.1659 0.0943 0.083 Uiso 1 1 calc R . .
H27B H 0.9496 0.2582 0.1263 0.083 Uiso 1 1 calc R . .
C28 C 0.8036(8) 0.2550(4) 0.05831(18) 0.1311(19) Uani 1 1 d U . .
H28 H 0.8693 0.2620 0.0276 0.157 Uiso 1 1 calc R . .
C29 C 0.6172(8) 0.2866(4) 0.0619(2) 0.147(2) Uani 1 1 d U . .
H29 H 0.5822 0.3461 0.0506 0.176 Uiso 1 1 calc R . .
N2 N 0.5988(3) 0.08191(13) 0.20229(7) 0.0399(5) Uani 1 1 d . . .
O2 O 0.3065(3) 0.09293(14) 0.16864(9) 0.0637(5) Uani 1 1 d . . .


_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
C15 C10 1.325(4) . ?
C15 C16 1.452(4) . ?
C15 C14 1.502(4) . ?
C16 O1 1.228(3) . ?
C16 N1 1.375(4) . ?
C10 C11 1.491(4) . ?
C10 C7 1.503(3) . ?
C7 N1 1.479(3) . ?
C7 C9 1.514(4) . ?
C7 C8 1.532(4) . ?
C11 C12 1.508(4) . ?
C5 C4 1.370(4) . ?
C5 C6 1.395(4) . ?
C5 C8 1.504(4) . ?
C6 C1 1.386(4) . ?
C6 N1 1.410(4) . ?
C4 C3 1.376(6) . ?
C13 C12 1.487(5) . ?
C13 C14 1.516(5) . ?
C1 C2 1.423(7) . ?
C2 C3 1.381(7) . ?
C26 C31 1.327(4) . ?
C26 C27 1.491(4) . ?
C26 C23 1.499(4) . ?
C25 C21 1.508(4) . ?
C25 C23 1.554(3) . ?
C32 O2 1.218(3) . ?
C32 N2 1.386(3) . ?
C32 C31 1.467(4) . ?
C22 C17 1.378(4) . ?
C22 C21 1.383(4) . ?
C22 N2 1.411(3) . ?
C31 C30 1.494(4) . ?
C23 N2 1.485(3) . ?
C23 C24 1.520(4) . ?
C21 C20 1.372(4) . ?
C17 C18 1.397(4) . ?
C20 C19 1.379(5) . ?
C30 C29 1.481(6) . ?
C18 C19 1.356(5) . ?
C27 C28 1.511(6) . ?
C28 C29 1.435(7) . ?

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
C10 C15 C16 110.0(2) . . ?
C10 C15 C14 124.3(3) . . ?
C16 C15 C14 125.7(2) . . ?
O1 C16 N1 123.9(3) . . ?
O1 C16 C15 129.1(3) . . ?
N1 C16 C15 106.9(2) . . ?
C15 C10 C11 124.3(2) . . ?
C15 C10 C7 110.3(2) . . ?
C11 C10 C7 125.2(2) . . ?
N1 C7 C10 101.57(19) . . ?
N1 C7 C9 110.1(2) . . ?
C10 C7 C9 111.4(2) . . ?
N1 C7 C8 103.4(2) . . ?
C10 C7 C8 118.4(2) . . ?
C9 C7 C8 111.0(2) . . ?
C10 C11 C12 110.4(3) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 C8 131.0(3) . . ?
C6 C5 C8 108.8(2) . . ?
C1 C6 C5 122.5(3) . . ?
C1 C6 N1 127.6(3) . . ?
C5 C6 N1 109.8(2) . . ?
C5 C8 C7 102.9(2) . . ?
C5 C4 C3 119.4(4) . . ?
C12 C13 C14 112.9(3) . . ?
C15 C14 C13 110.0(3) . . ?
C13 C12 C11 113.5(3) . . ?
C6 C1 C2 115.6(4) . . ?
C3 C2 C1 121.6(4) . . ?
C4 C3 C2 120.6(4) . . ?
C16 N1 C6 127.8(2) . . ?
C16 N1 C7 110.8(2) . . ?
C6 N1 C7 108.7(2) . . ?
C31 C26 C27 124.0(3) . . ?
C31 C26 C23 111.0(2) . . ?
C27 C26 C23 124.8(3) . . ?
C21 C25 C23 101.5(2) . . ?
O2 C32 N2 124.6(2) . . ?
O2 C32 C31 129.5(3) . . ?
N2 C32 C31 105.8(2) . . ?
C17 C22 C21 122.4(2) . . ?
C17 C22 N2 128.1(3) . . ?
C21 C22 N2 109.5(2) . . ?
C26 C31 C32 110.1(2) . . ?
C26 C31 C30 125.5(2) . . ?
C32 C31 C30 124.4(3) . . ?
N2 C23 C26 101.30(19) . . ?
N2 C23 C24 110.4(2) . . ?
C26 C23 C24 112.8(2) . . ?
N2 C23 C25 102.59(19) . . ?
C26 C23 C25 118.8(2) . . ?
C24 C23 C25 109.8(2) . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 C25 130.6(3) . . ?
C22 C21 C25 109.9(2) . . ?
C22 C17 C18 116.3(3) . . ?
C21 C20 C19 119.2(3) . . ?
C29 C30 C31 109.8(3) . . ?
C19 C18 C17 121.9(3) . . ?
C18 C19 C20 120.7(3) . . ?
C26 C27 C28 109.9(3) . . ?
C29 C28 C27 118.8(3) . . ?
C28 C29 C30 116.8(4) . . ?
C32 N2 C22 126.1(2) . . ?
C32 N2 C23 111.20(19) . . ?
C22 N2 C23 108.68(19) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.036
