# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1859567'
_audit_update_record             
;
2018-08-01 deposited with the CCDC.
2018-10-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H18 N2 O2'
_chemical_formula_sum            'C20 H18 N2 O2'
_chemical_formula_weight         318.36

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'

_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                   7.8748(4)
_cell_length_b                   14.7543(6)
_cell_length_c                   15.7507(6)
_cell_angle_alpha                68.6045(14)
_cell_angle_beta                 85.8107(17)
_cell_angle_gamma                77.4717(17)
_cell_volume                     1663.30(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8071
_cell_measurement_theta_min      2.8534
_cell_measurement_theta_max      27.5119

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   SADABS



_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14975
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.778
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.910
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.910
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.910
_reflns_number_total             5483
_reflns_number_gt                3778
_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       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0534P)²+3.1943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5483
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0899
_refine_ls_wR_factor_ref         0.2241
_refine_ls_wR_factor_gt          0.2091
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_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_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 0.7892(5) 0.5261(3) 0.4037(3) 0.0373(9) Uani 1 1 d . . . . .
C2 C 0.9246(6) 0.5189(4) 0.3452(3) 0.0549(12) Uani 1 1 d . . . . .
H2A H 0.9236 0.5680 0.2877 0.066 Uiso 1 1 calc R U . . .
C3 C 1.0626(6) 0.4386(4) 0.3716(4) 0.0699(15) Uani 1 1 d . . . . .
H3 H 1.1536 0.4332 0.3315 0.084 Uiso 1 1 calc R U . . .
C4 C 1.0660(7) 0.3668(4) 0.4565(4) 0.0687(15) Uani 1 1 d . . . . .
H4 H 1.1593 0.3129 0.4750 0.082 Uiso 1 1 calc R U . . .
C5 C 0.9300(6) 0.3757(4) 0.5134(4) 0.0681(15) Uani 1 1 d . . . . .
H5 H 0.9299 0.3265 0.5707 0.082 Uiso 1 1 calc R U . . .
C6 C 0.6084(5) 0.6847(3) 0.3135(3) 0.0375(9) Uani 1 1 d . . . . .
C7 C 0.4225(5) 0.7406(3) 0.3008(2) 0.0349(9) Uani 1 1 d . . . . .
C8 C 0.3636(5) 0.8160(3) 0.3356(3) 0.0399(10) Uani 1 1 d . . . . .
C9 C 0.1916(6) 0.8680(3) 0.3189(3) 0.0551(12) Uani 1 1 d . . . . .
H9 H 0.1501 0.9181 0.3423 0.066 Uiso 1 1 calc R U . . .
C10 C 0.0830(6) 0.8456(4) 0.2681(3) 0.0580(13) Uani 1 1 d . . . . .
H10 H -0.0309 0.8814 0.2566 0.070 Uiso 1 1 calc R U . . .
C11 C 0.1417(6) 0.7709(3) 0.2345(3) 0.0500(11) Uani 1 1 d . . . . .
H11 H 0.0667 0.7563 0.2006 0.060 Uiso 1 1 calc R U . . .
C12 C 0.3105(5) 0.7168(3) 0.2502(3) 0.0412(10) Uani 1 1 d . . . . .
C13 C 0.4769(5) 0.8411(3) 0.3920(3) 0.0413(10) Uani 1 1 d . . . . .
C14 C 0.4474(7) 0.8197(4) 0.4836(3) 0.0644(14) Uani 1 1 d . . . . .
H14 H 0.3578 0.7872 0.5108 0.077 Uiso 1 1 calc R U . . .
C15 C 0.5479(7) 0.8455(4) 0.5363(3) 0.0688(15) Uani 1 1 d . . . . .
H15 H 0.5253 0.8292 0.5983 0.083 Uiso 1 1 calc R U . . .
C16 C 0.6791(6) 0.8942(3) 0.4991(3) 0.0523(12) Uani 1 1 d . . . . .
C17 C 0.7073(7) 0.9165(5) 0.4086(4) 0.0769(17) Uani 1 1 d . . . . .
H17 H 0.7955 0.9503 0.3815 0.092 Uiso 1 1 calc R U . . .
C18 C 0.6083(7) 0.8904(5) 0.3548(4) 0.0743(16) Uani 1 1 d . . . . .
H18 H 0.6317 0.9068 0.2928 0.089 Uiso 1 1 calc R U . . .
C19 C 0.7883(8) 0.9222(4) 0.5569(4) 0.0820(18) Uani 1 1 d . . . . .
H19A H 0.7512 0.8987 0.6192 0.123 Uiso 1 1 calc R U . . .
H19B H 0.7748 0.9932 0.5352 0.123 Uiso 1 1 calc R U . . .
H19C H 0.9084 0.8923 0.5531 0.123 Uiso 1 1 calc R U . . .
C20 C 0.3703(7) 0.6319(4) 0.2168(3) 0.0626(13) Uani 1 1 d . . . . .
H20A H 0.2839 0.6325 0.1766 0.094 Uiso 1 1 calc R U . . .
H20B H 0.3872 0.5702 0.2679 0.094 Uiso 1 1 calc R U . . .
H20C H 0.4779 0.6387 0.1847 0.094 Uiso 1 1 calc R U . . .
C21 C 0.1951(5) 0.4811(3) 0.0962(3) 0.0345(9) Uani 1 1 d . . . . .
C22 C 0.0307(5) 0.4668(3) 0.1273(3) 0.0467(11) Uani 1 1 d . . . . .
H22 H 0.0155 0.4046 0.1668 0.056 Uiso 1 1 calc R U . . .
C23 C -0.1105(6) 0.5447(4) 0.0997(3) 0.0608(13) Uani 1 1 d . . . . .
H23 H -0.2212 0.5351 0.1204 0.073 Uiso 1 1 calc R U . . .
C24 C -0.0875(6) 0.6358(4) 0.0419(4) 0.0612(13) Uani 1 1 d . . . . .
H24 H -0.1820 0.6889 0.0233 0.073 Uiso 1 1 calc R U . . .
C25 C 0.0750(6) 0.6481(3) 0.0120(3) 0.0537(12) Uani 1 1 d . . . . .
H25 H 0.0907 0.7101 -0.0280 0.064 Uiso 1 1 calc R U . . .
C26 C 0.3763(5) 0.3209(3) 0.1862(3) 0.0345(9) Uani 1 1 d . . . . .
C27 C 0.5622(5) 0.2657(3) 0.2002(3) 0.0338(9) Uani 1 1 d . . . . .
C28 C 0.6214(5) 0.1888(3) 0.1669(3) 0.0365(9) Uani 1 1 d . . . . .
C29 C 0.7942(5) 0.1376(3) 0.1841(3) 0.0517(12) Uani 1 1 d . . . . .
H29 H 0.8368 0.0871 0.1613 0.062 Uiso 1 1 calc R U . . .
C30 C 0.9023(6) 0.1613(4) 0.2344(3) 0.0574(13) Uani 1 1 d . . . . .
H30 H 1.0165 0.1260 0.2462 0.069 Uiso 1 1 calc R U . . .
C31 C 0.8418(6) 0.2368(3) 0.2671(3) 0.0505(11) Uani 1 1 d . . . . .
H31 H 0.9160 0.2523 0.3007 0.061 Uiso 1 1 calc R U . . .
C32 C 0.6720(5) 0.2902(3) 0.2509(3) 0.0400(10) Uani 1 1 d . . . . .
C33 C 0.5103(5) 0.1618(3) 0.1110(3) 0.0397(10) Uani 1 1 d . . . . .
C34 C 0.5402(6) 0.1835(3) 0.0189(3) 0.0559(12) Uani 1 1 d . . . . .
H34 H 0.6264 0.2186 -0.0089 0.067 Uiso 1 1 calc R U . . .
C35 C 0.4441(7) 0.1539(4) -0.0327(3) 0.0599(13) Uani 1 1 d . . . . .
H35 H 0.4672 0.1696 -0.0946 0.072 Uiso 1 1 calc R U . . .
C36 C 0.3165(6) 0.1024(3) 0.0051(3) 0.0513(12) Uani 1 1 d . . . . .
C37 C 0.2867(7) 0.0807(5) 0.0958(4) 0.0742(16) Uani 1 1 d . . . . .
H37 H 0.2005 0.0454 0.1231 0.089 Uiso 1 1 calc R U . . .
C38 C 0.3820(7) 0.1098(4) 0.1489(4) 0.0701(15) Uani 1 1 d . . . . .
H38 H 0.3583 0.0937 0.2108 0.084 Uiso 1 1 calc R U . . .
C39 C 0.2118(7) 0.0713(4) -0.0522(4) 0.0807(18) Uani 1 1 d . . . . .
H39A H 0.0917 0.1030 -0.0523 0.121 Uiso 1 1 calc R U . . .
H39B H 0.2226 0.0004 -0.0273 0.121 Uiso 1 1 calc R U . . .
H39C H 0.2545 0.0906 -0.1136 0.121 Uiso 1 1 calc R U . . .
C40 C 0.6098(6) 0.3726(4) 0.2872(4) 0.0606(13) Uani 1 1 d . . . . .
H40A H 0.7014 0.3766 0.3219 0.091 Uiso 1 1 calc R U . . .
H40B H 0.5109 0.3594 0.3256 0.091 Uiso 1 1 calc R U . . .
H40C H 0.5774 0.4344 0.2372 0.091 Uiso 1 1 calc R U . . .
N1 N 0.7946(4) 0.4548(3) 0.4883(3) 0.0545(10) Uani 1 1 d . . . . .
N2 N 0.6379(4) 0.5977(2) 0.3861(2) 0.0388(8) Uani 1 1 d . . . . .
H2 H 0.5546 0.5862 0.4244 0.047 Uiso 1 1 calc R U . . .
N3 N 0.2151(4) 0.5721(2) 0.0390(2) 0.0388(8) Uani 1 1 d . . . . .
N4 N 0.3491(4) 0.4107(2) 0.1165(2) 0.0362(8) Uani 1 1 d . . . . .
H4A H 0.4361 0.4250 0.0815 0.043 Uiso 1 1 calc R U . . .
O1 O 0.6699(4) 0.4651(3) 0.5475(2) 0.0751(11) Uani 1 1 d . . . . .
O2 O 0.7211(4) 0.7151(2) 0.2606(2) 0.0649(10) Uani 1 1 d . . . . .
O3 O 0.3711(4) 0.5868(2) 0.0103(2) 0.0548(8) Uani 1 1 d . . . . .
O4 O 0.2618(4) 0.2893(2) 0.2365(2) 0.0584(9) 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 N1 1.361(5) . ?
C1 C2 1.370(6) . ?
C1 N2 1.378(5) . ?
C2 C3 1.380(6) . ?
C3 C4 1.368(7) . ?
C4 C5 1.360(7) . ?
C5 N1 1.357(6) . ?
C6 O2 1.215(5) . ?
C6 N2 1.360(5) . ?
C6 C7 1.504(5) . ?
C7 C8 1.391(5) . ?
C7 C12 1.406(5) . ?
C8 C9 1.395(6) . ?
C8 C13 1.490(6) . ?
C9 C10 1.378(6) . ?
C10 C11 1.371(6) . ?
C11 C12 1.382(6) . ?
C12 C20 1.502(6) . ?
C13 C18 1.368(6) . ?
C13 C14 1.373(6) . ?
C14 C15 1.384(7) . ?
C15 C16 1.362(7) . ?
C16 C17 1.354(7) . ?
C16 C19 1.511(6) . ?
C17 C18 1.393(7) . ?
C21 N3 1.351(5) . ?
C21 C22 1.382(5) . ?
C21 N4 1.386(5) . ?
C22 C23 1.378(6) . ?
C23 C24 1.363(7) . ?
C24 C25 1.358(7) . ?
C25 N3 1.356(5) . ?
C26 O4 1.212(4) . ?
C26 N4 1.363(5) . ?
C26 C27 1.501(5) . ?
C27 C28 1.396(5) . ?
C27 C32 1.400(5) . ?
C28 C29 1.398(5) . ?
C28 C33 1.490(5) . ?
C29 C30 1.379(6) . ?
C30 C31 1.373(7) . ?
C31 C32 1.386(6) . ?
C32 C40 1.501(6) . ?
C33 C38 1.372(6) . ?
C33 C34 1.380(6) . ?
C34 C35 1.384(6) . ?
C35 C36 1.362(7) . ?
C36 C37 1.359(7) . ?
C36 C39 1.512(6) . ?
C37 C38 1.393(7) . ?
N1 O1 1.327(5) . ?
N3 O3 1.313(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
N1 C1 C2 119.3(4) . . ?
N1 C1 N2 113.5(3) . . ?
C2 C1 N2 127.2(4) . . ?
C1 C2 C3 120.0(5) . . ?
C4 C3 C2 120.3(5) . . ?
C5 C4 C3 118.7(5) . . ?
N1 C5 C4 121.5(5) . . ?
O2 C6 N2 123.4(4) . . ?
O2 C6 C7 121.5(4) . . ?
N2 C6 C7 115.0(3) . . ?
C8 C7 C12 120.6(4) . . ?
C8 C7 C6 121.2(3) . . ?
C12 C7 C6 118.2(3) . . ?
C7 C8 C9 118.8(4) . . ?
C7 C8 C13 122.1(3) . . ?
C9 C8 C13 119.0(4) . . ?
C10 C9 C8 120.4(4) . . ?
C11 C10 C9 120.4(4) . . ?
C10 C11 C12 121.0(4) . . ?
C11 C12 C7 118.7(4) . . ?
C11 C12 C20 120.4(4) . . ?
C7 C12 C20 120.9(4) . . ?
C18 C13 C14 117.0(4) . . ?
C18 C13 C8 122.1(4) . . ?
C14 C13 C8 120.8(4) . . ?
C13 C14 C15 121.5(5) . . ?
C16 C15 C14 121.3(5) . . ?
C17 C16 C15 117.4(4) . . ?
C17 C16 C19 121.6(5) . . ?
C15 C16 C19 121.1(5) . . ?
C16 C17 C18 122.1(5) . . ?
C13 C18 C17 120.7(5) . . ?
N3 C21 C22 119.2(3) . . ?
N3 C21 N4 113.7(3) . . ?
C22 C21 N4 127.1(4) . . ?
C23 C22 C21 120.0(4) . . ?
C24 C23 C22 119.8(4) . . ?
C25 C24 C23 119.2(4) . . ?
N3 C25 C24 121.5(4) . . ?
O4 C26 N4 123.1(3) . . ?
O4 C26 C27 121.8(3) . . ?
N4 C26 C27 115.0(3) . . ?
C28 C27 C32 121.0(3) . . ?
C28 C27 C26 120.5(3) . . ?
C32 C27 C26 118.4(3) . . ?
C27 C28 C29 118.4(4) . . ?
C27 C28 C33 122.8(3) . . ?
C29 C28 C33 118.8(4) . . ?
C30 C29 C28 120.7(4) . . ?
C31 C30 C29 120.2(4) . . ?
C30 C31 C32 121.0(4) . . ?
C31 C32 C27 118.7(4) . . ?
C31 C32 C40 119.8(4) . . ?
C27 C32 C40 121.5(4) . . ?
C38 C33 C34 117.2(4) . . ?
C38 C33 C28 122.0(4) . . ?
C34 C33 C28 120.7(4) . . ?
C33 C34 C35 121.2(4) . . ?
C36 C35 C34 121.5(5) . . ?
C37 C36 C35 117.6(4) . . ?
C37 C36 C39 121.5(5) . . ?
C35 C36 C39 120.9(5) . . ?
C36 C37 C38 121.7(5) . . ?
C33 C38 C37 120.8(5) . . ?
O1 N1 C5 120.1(4) . . ?
O1 N1 C1 119.5(3) . . ?
C5 N1 C1 120.3(4) . . ?
C6 N2 C1 125.9(3) . . ?
O3 N3 C21 119.7(3) . . ?
O3 N3 C25 120.1(3) . . ?
C21 N3 C25 120.3(4) . . ?
C26 N4 C21 126.4(3) . . ?

_refine_diff_density_max         0.671
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3



