# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_mo_20170619py_dbn_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1572151'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2017-11-22 downloaded from the CCDC.
;
_audit_creation_date             2017-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N3 O'
_chemical_formula_sum            'C27 H23 N3 O'
_chemical_formula_weight         405.48
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'

_cell_length_a                   31.825(9)
_cell_length_b                   31.825(9)
_cell_length_c                   8.303(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8409(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    6792
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3424
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            22708
_diffrn_reflns_point_group_measured_fraction_full 0.818
_diffrn_reflns_point_group_measured_fraction_max 0.818
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.024
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.525
_reflns_Friedel_fraction_full    0.611
_reflns_Friedel_fraction_max     0.611
_reflns_number_gt                2842
_reflns_number_total             3034
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+2.3597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0969
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1 C -1.28791(7) -0.94307(7) -1.6591(3) 0.0206(6) Uani 1 1 d . . . . .
C2 C -1.26691(7) -0.98055(8) -1.6165(4) 0.0254(6) Uani 1 1 d . . . . .
H2 H -1.278850 -0.998797 -1.541949 0.030 Uiso 1 1 calc R . . . .
C3 C -1.22889(8) -0.99000(8) -1.6852(4) 0.0300(7) Uani 1 1 d . . . . .
H3 H -1.214903 -1.014500 -1.655994 0.036 Uiso 1 1 calc R . . . .
C4 C -1.21118(8) -0.96311(9) -1.7983(4) 0.0338(7) Uani 1 1 d . . . . .
H4 H -1.185673 -0.970115 -1.845910 0.041 Uiso 1 1 calc R . . . .
C5 C -1.23082(8) -0.92645(9) -1.8405(4) 0.0305(7) Uani 1 1 d . . . . .
H5 H -1.218439 -0.908777 -1.916011 0.037 Uiso 1 1 calc R . . . .
C6 C -1.26964(7) -0.91516(8) -1.7705(3) 0.0218(6) Uani 1 1 d . . . . .
C7 C -1.29024(7) -0.87528(8) -1.7987(3) 0.0225(6) Uani 1 1 d . . . . .
C8 C -1.27454(8) -0.84433(9) -1.9036(4) 0.0295(6) Uani 1 1 d . . . . .
H8 H -1.250903 -0.849765 -1.966075 0.035 Uiso 1 1 calc R . . . .
C9 C -1.29428(9) -0.80611(9) -1.9133(4) 0.0352(7) Uani 1 1 d . . . . .
H9 H -1.284110 -0.786002 -1.984641 0.042 Uiso 1 1 calc R . . . .
C10 C -1.32919(8) -0.79671(8) -1.8188(4) 0.0315(7) Uani 1 1 d . . . . .
H10 H -1.341433 -0.770225 -1.825115 0.038 Uiso 1 1 calc R . . . .
C11 C -1.34570(7) -0.82643(7) -1.7161(4) 0.0227(6) Uani 1 1 d . . . . .
C12 C -1.32704(7) -0.86686(7) -1.7096(3) 0.0197(5) Uani 1 1 d . . . . .
C13 C -1.39149(10) -0.77250(8) -1.5921(5) 0.0378(8) Uani 1 1 d . . . . .
H13A H -1.409884 -0.769765 -1.501058 0.057 Uiso 1 1 calc GR . . . .
H13B H -1.405638 -0.762893 -1.687314 0.057 Uiso 1 1 calc GR . . . .
H13C H -1.366705 -0.755909 -1.574784 0.057 Uiso 1 1 calc GR . . . .
C14 C -1.39810(7) -0.84555(8) -1.5132(3) 0.0226(6) Uani 1 1 d . . . . .
C15 C -1.38779(7) -0.89213(7) -1.5379(3) 0.0205(6) Uani 1 1 d . . . . .
C16 C -1.34436(7) -0.89911(7) -1.6105(3) 0.0194(5) Uani 1 1 d . . . . .
C17 C -1.42087(7) -0.90957(8) -1.6589(4) 0.0229(6) Uani 1 1 d . . . . .
C18 C -1.45279(8) -0.88486(8) -1.7224(4) 0.0262(6) Uani 1 1 d . . . . .
H18 H -1.454916 -0.856812 -1.691973 0.031 Uiso 1 1 calc R . . . .
C19 C -1.48157(8) -0.90153(9) -1.8307(4) 0.0308(6) Uani 1 1 d . . . . .
H19 H -1.502554 -0.884485 -1.873236 0.037 Uiso 1 1 calc R . . . .
C20 C -1.47926(8) -0.94296(9) -1.8753(4) 0.0362(7) Uani 1 1 d . . . . .
H20 H -1.498644 -0.954108 -1.947375 0.043 Uiso 1 1 calc R . . . .
C21 C -1.44767(9) -0.96813(9) -1.8117(5) 0.0400(8) Uani 1 1 d . . . . .
H21 H -1.445966 -0.996297 -1.840843 0.048 Uiso 1 1 calc R . . . .
C22 C -1.41876(8) -0.95142(8) -1.7052(4) 0.0317(7) Uani 1 1 d . . . . .
H22 H -1.397601 -0.968468 -1.663916 0.038 Uiso 1 1 calc R . . . .
C23 C -1.39258(7) -0.91523(8) -1.3766(4) 0.0219(6) Uani 1 1 d . . . . .
H23A H -1.387096 -0.944808 -1.395370 0.026 Uiso 1 1 calc R . . . .
H23B H -1.421678 -0.912796 -1.343108 0.026 Uiso 1 1 calc R . . . .
C24 C -1.36419(8) -0.90059(8) -1.2324(4) 0.0242(6) Uani 1 1 d . . . . .
C25 C -1.39138(10) -0.88814(10) -1.0879(4) 0.0384(7) Uani 1 1 d . . . . .
H25A H -1.409976 -0.865766 -1.118402 0.058 Uiso 1 1 calc GR . . . .
H25B H -1.373645 -0.878921 -1.001293 0.058 Uiso 1 1 calc GR . . . .
H25C H -1.407578 -0.911946 -1.053342 0.058 Uiso 1 1 calc GR . . . .
C26 C -1.33332(9) -0.93561(9) -1.1826(4) 0.0357(7) Uani 1 1 d . . . . .
H26A H -1.315504 -0.925601 -1.097590 0.054 Uiso 1 1 calc GR . . . .
H26B H -1.316412 -0.943409 -1.273598 0.054 Uiso 1 1 calc GR . . . .
H26C H -1.348831 -0.959629 -1.145757 0.054 Uiso 1 1 calc GR . . . .
C27 C -1.33880(8) -0.86328(8) -1.2764(4) 0.0268(6) Uani 1 1 d . . . . .
N1 N -1.37959(6) -0.81684(6) -1.6121(3) 0.0228(5) Uani 1 1 d . . . . .
N2 N -1.32620(6) -0.93518(6) -1.5838(3) 0.0201(5) Uani 1 1 d . . . . .
N3 N -1.31929(8) -0.83407(8) -1.3074(4) 0.0378(6) Uani 1 1 d . . . . .
O1 O -1.42456(6) -0.83546(6) -1.4137(3) 0.0284(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
C1 C2 1.412(3) . ?
C1 C6 1.408(4) . ?
C1 N2 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.411(4) . ?
C6 C7 1.448(4) . ?
C7 C8 1.406(4) . ?
C7 C12 1.411(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.371(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C11 C12 1.418(3) . ?
C11 N1 1.415(4) . ?
C12 C16 1.426(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 N1 1.470(3) . ?
C14 C15 1.532(3) . ?
C14 N1 1.363(3) . ?
C14 O1 1.222(3) . ?
C15 C16 1.524(3) . ?
C15 C17 1.558(4) . ?
C15 C23 1.535(4) . ?
C16 N2 1.304(3) . ?
C17 C18 1.388(4) . ?
C17 C22 1.388(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.390(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(4) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.571(4) . ?
C24 C25 1.531(4) . ?
C24 C26 1.542(4) . ?
C24 C27 1.482(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 N3 1.147(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
C6 C1 C2 120.1(2) . . ?
N2 C1 C2 117.0(2) . . ?
N2 C1 C6 122.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 C7 118.2(2) . . ?
C5 C6 C7 123.6(2) . . ?
C8 C7 C6 123.6(2) . . ?
C8 C7 C12 119.1(2) . . ?
C12 C7 C6 117.2(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.7(3) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.5(3) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 N1 121.4(2) . . ?
N1 C11 C12 119.4(2) . . ?
C7 C12 C11 120.0(2) . . ?
C7 C12 C16 119.1(2) . . ?
C11 C12 C16 120.9(2) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
N1 C14 C15 118.4(2) . . ?
O1 C14 C15 119.5(2) . . ?
O1 C14 N1 121.9(2) . . ?
C14 C15 C17 106.6(2) . . ?
C14 C15 C23 109.0(2) . . ?
C16 C15 C14 112.86(19) . . ?
C16 C15 C17 107.8(2) . . ?
C16 C15 C23 111.4(2) . . ?
C23 C15 C17 108.96(19) . . ?
C12 C16 C15 118.3(2) . . ?
N2 C16 C12 124.1(2) . . ?
N2 C16 C15 117.6(2) . . ?
C18 C17 C15 122.5(2) . . ?
C22 C17 C15 119.2(2) . . ?
C22 C17 C18 118.3(3) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.8(2) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.2(3) . . ?
C22 C21 H21 119.9 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 120.9(3) . . ?
C21 C22 H22 119.5 . . ?
C15 C23 H23A 107.9 . . ?
C15 C23 H23B 107.9 . . ?
C15 C23 C24 117.8(2) . . ?
H23A C23 H23B 107.2 . . ?
C24 C23 H23A 107.9 . . ?
C24 C23 H23B 107.9 . . ?
C25 C24 C23 110.4(2) . . ?
C25 C24 C26 109.7(3) . . ?
C26 C24 C23 110.9(2) . . ?
C27 C24 C23 111.3(2) . . ?
C27 C24 C25 107.1(2) . . ?
C27 C24 C26 107.3(2) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C27 C24 178.6(3) . . ?
C11 N1 C13 118.2(2) . . ?
C14 N1 C11 123.57(19) . . ?
C14 N1 C13 117.6(2) . . ?
C16 N2 C1 118.0(2) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
