# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1444563'
_audit_update_record             
;
2015-12-29 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 N O3'
_chemical_formula_weight         369.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.30340(10)
_cell_length_b                   9.6541(2)
_cell_length_c                   11.6687(8)
_cell_angle_alpha                101.875(7)
_cell_angle_beta                 106.962(8)
_cell_angle_gamma                96.397(7)
_cell_volume                     964.39(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11207
_cell_measurement_theta_min      7.00
_cell_measurement_theta_max      68.30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.493
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13309
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         7.023
_diffrn_reflns_theta_max         68.334
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             3411
_reflns_number_gt                3039
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0753P)²+0.1682P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3411
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60930(12) -0.04693(12) 0.91322(12) 0.0541(3) Uani 1 1 d . . . . .
O2 O 0.78294(13) 0.45019(12) 0.98567(12) 0.0591(3) Uani 1 1 d . . . . .
O1W O 0.36312(17) -0.29962(16) 0.78010(15) 0.0760(4) Uani 1 1 d . . . . .
H1O H 0.4489 -0.2529 0.8304 0.091 Uiso 1 1 d R U . . .
H2O H 0.2956 -0.2834 0.8144 0.091 Uiso 1 1 d R U . . .
N1 N 0.84692(13) 0.20588(14) 1.08998(11) 0.0438(3) Uani 1 1 d . . . . .
C1 C 0.23520(18) 0.1791(2) 0.75878(17) 0.0604(5) Uani 1 1 d . . . . .
H1 H 0.1320 0.1415 0.7179 0.073 Uiso 1 1 calc R U . . .
C2 C 0.33305(17) 0.08843(19) 0.79813(16) 0.0521(4) Uani 1 1 d . . . . .
H2 H 0.2974 -0.0092 0.7853 0.062 Uiso 1 1 calc R U . . .
C3 C 0.48704(16) 0.14834(16) 0.85770(13) 0.0416(3) Uani 1 1 d . . . . .
C4 C 0.61485(16) 0.07853(16) 0.91023(13) 0.0408(3) Uani 1 1 d . . . . .
C5 C 0.76226(15) 0.19062(15) 0.95979(13) 0.0398(3) Uani 1 1 d . . . . .
C7 C 0.99058(16) 0.22668(15) 1.10472(14) 0.0403(3) Uani 1 1 d . . . . .
C8 C 1.10525(16) 0.25720(16) 1.22869(14) 0.0440(4) Uani 1 1 d . . . . .
C9 C 1.25896(17) 0.30295(18) 1.24676(16) 0.0512(4) Uani 1 1 d . . . . .
H9 H 1.2904 0.3125 1.1796 0.061 Uiso 1 1 calc R U . . .
C10 C 1.3656(2) 0.3344(2) 1.36376(18) 0.0626(5) Uani 1 1 d . . . . .
H10 H 1.4682 0.3654 1.3750 0.075 Uiso 1 1 calc R U . . .
C11 C 1.3206(2) 0.3201(2) 1.46336(18) 0.0691(5) Uani 1 1 d . . . . .
H11 H 1.3925 0.3410 1.5419 0.083 Uiso 1 1 calc R U . . .
C12 C 0.7640(3) 0.2438(3) 0.53017(19) 0.0748(6) Uani 1 1 d . . . . .
H12 H 0.7386 0.2626 0.4524 0.090 Uiso 1 1 calc R U . . .
C13 C 0.7133(3) 0.1096(3) 0.54340(19) 0.0799(6) Uani 1 1 d . . . . .
H13 H 0.6533 0.0377 0.4742 0.096 Uiso 1 1 calc R U . . .
C14 C 0.7513(2) 0.0820(2) 0.65902(16) 0.0606(5) Uani 1 1 d . . . . .
H14 H 0.7168 -0.0085 0.6670 0.073 Uiso 1 1 calc R U . . .
C15 C 0.84051(16) 0.18802(16) 0.76371(14) 0.0419(3) Uani 1 1 d . . . . .
C16 C 0.87607(15) 0.15197(15) 0.88789(13) 0.0392(3) Uani 1 1 d . . . . .
H16 H 0.8699 0.0474 0.8720 0.047 Uiso 1 1 calc R U . . .
C17 C 1.03020(16) 0.22042(17) 0.98795(14) 0.0433(4) Uani 1 1 d . . . . .
H17A H 1.1068 0.1611 0.9830 0.052 Uiso 1 1 calc R U . . .
H17B H 1.0667 0.3159 0.9818 0.052 Uiso 1 1 calc R U . . .
C18 C 0.53909(16) 0.29478(16) 0.87664(14) 0.0419(3) Uani 1 1 d . . . . .
C19 C 0.44007(19) 0.38562(19) 0.83761(16) 0.0525(4) Uani 1 1 d . . . . .
H19 H 0.4751 0.4834 0.8505 0.063 Uiso 1 1 calc R U . . .
C20 C 0.2878(2) 0.3254(2) 0.77897(16) 0.0596(5) Uani 1 1 d . . . . .
H20 H 0.2188 0.3839 0.7523 0.071 Uiso 1 1 calc R U . . .
C21 C 0.70466(16) 0.33119(16) 0.94450(14) 0.0424(3) Uani 1 1 d . . . . .
C22 C 1.1679(2) 0.2745(2) 1.44658(17) 0.0686(5) Uani 1 1 d . . . . .
H22 H 1.1373 0.2649 1.5140 0.082 Uiso 1 1 calc R U . . .
C23 C 1.0614(2) 0.2436(2) 1.33076(16) 0.0573(4) Uani 1 1 d . . . . .
H23 H 0.9590 0.2132 1.3204 0.069 Uiso 1 1 calc R U . . .
C24 C 0.89043(19) 0.32231(18) 0.74922(16) 0.0516(4) Uani 1 1 d . . . . .
H24 H 0.9498 0.3948 0.8182 0.062 Uiso 1 1 calc R U . . .
C25 C 0.8527(2) 0.3493(2) 0.63347(19) 0.0649(5) Uani 1 1 d . . . . .
H25 H 0.8875 0.4396 0.6251 0.078 Uiso 1 1 calc R U . . .


_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 C4 1.2147(18) . ?
O2 C21 1.2096(18) . ?
O1W H1O 0.8500 . ?
O1W H2O 0.8500 . ?
N1 C7 1.2838(18) . ?
N1 C5 1.4608(19) . ?
C1 C2 1.380(2) . ?
C1 C20 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.392(2) . ?
C2 H2 0.9300 . ?
C3 C18 1.392(2) . ?
C3 C4 1.472(2) . ?
C4 C5 1.5281(19) . ?
C5 C21 1.538(2) . ?
C5 C16 1.563(2) . ?
C7 C8 1.474(2) . ?
C7 C17 1.503(2) . ?
C8 C9 1.389(2) . ?
C8 C23 1.392(2) . ?
C9 C10 1.383(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C22 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C25 1.378(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9300 . ?
C15 C24 1.388(2) . ?
C15 C16 1.511(2) . ?
C16 C17 1.533(2) . ?
C16 H16 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.387(2) . ?
C18 C21 1.475(2) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 C23 1.373(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C25 1.380(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

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
H1O O1W H2O 107.7 . . ?
C7 N1 C5 108.79(12) . . ?
C2 C1 C20 121.31(15) . . ?
C2 C1 H1 119.3 . . ?
C20 C1 H1 119.3 . . ?
C1 C2 C3 117.67(16) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C18 C3 C2 120.68(14) . . ?
C18 C3 C4 110.07(12) . . ?
C2 C3 C4 129.25(14) . . ?
O1 C4 C3 127.46(13) . . ?
O1 C4 C5 124.04(13) . . ?
C3 C4 C5 108.49(12) . . ?
N1 C5 C4 113.89(12) . . ?
N1 C5 C21 109.33(12) . . ?
C4 C5 C21 102.98(11) . . ?
N1 C5 C16 105.62(11) . . ?
C4 C5 C16 111.64(11) . . ?
C21 C5 C16 113.59(12) . . ?
N1 C7 C8 121.14(13) . . ?
N1 C7 C17 115.08(13) . . ?
C8 C7 C17 123.77(12) . . ?
C9 C8 C23 118.52(15) . . ?
C9 C8 C7 120.79(14) . . ?
C23 C8 C7 120.67(14) . . ?
C10 C9 C8 120.52(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.24(17) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C22 119.80(17) . . ?
C10 C11 H11 120.1 . . ?
C22 C11 H11 120.1 . . ?
C25 C12 C13 119.30(18) . . ?
C25 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.83(19) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C24 C15 C14 118.40(15) . . ?
C24 C15 C16 123.27(14) . . ?
C14 C15 C16 118.32(14) . . ?
C15 C16 C17 119.34(12) . . ?
C15 C16 C5 114.95(12) . . ?
C17 C16 C5 101.26(11) . . ?
C15 C16 H16 106.8 . . ?
C17 C16 H16 106.8 . . ?
C5 C16 H16 106.8 . . ?
C7 C17 C16 101.91(11) . . ?
C7 C17 H17A 111.4 . . ?
C16 C17 H17A 111.4 . . ?
C7 C17 H17B 111.4 . . ?
C16 C17 H17B 111.4 . . ?
H17A C17 H17B 109.3 . . ?
C19 C18 C3 121.43(14) . . ?
C19 C18 C21 128.65(14) . . ?
C3 C18 C21 109.89(13) . . ?
C20 C19 C18 117.47(16) . . ?
C20 C19 H19 121.3 . . ?
C18 C19 H19 121.3 . . ?
C19 C20 C1 121.44(16) . . ?
C19 C20 H20 119.3 . . ?
C1 C20 H20 119.3 . . ?
O2 C21 C18 127.01(14) . . ?
O2 C21 C5 124.82(13) . . ?
C18 C21 C5 108.12(12) . . ?
C23 C22 C11 120.27(18) . . ?
C23 C22 H22 119.9 . . ?
C11 C22 H22 119.9 . . ?
C22 C23 C8 120.65(17) . . ?
C22 C23 H23 119.7 . . ?
C8 C23 H23 119.7 . . ?
C25 C24 C15 120.61(17) . . ?
C25 C24 H24 119.7 . . ?
C15 C24 H24 119.7 . . ?
C12 C25 C24 120.66(19) . . ?
C12 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1O O1 0.85 2.20 2.9545(19) 148.6 .
O1W H2O N1 0.85 2.07 2.9143(19) 169.5 2_657
C17 H17B O2 0.97 2.42 3.3589(19) 164.0 2_767

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-3



