# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1575437'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2018-04-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H18 N2 O2'
_chemical_formula_sum            'C24 H18 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         366.40

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.348(4)
_cell_length_b                   9.871(2)
_cell_length_c                   17.745(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.423(5)
_cell_angle_gamma                90
_cell_volume                     3736.0(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3528
_cell_measurement_theta_min      2.2735
_cell_measurement_theta_max      20.1237
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   fine-focus
_diffrn_source_type              'sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333


_diffrn_reflns_number            26924
_diffrn_reflns_av_R_equivalents  0.0801
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_refine_special_details          
;
;

_reflns_number_total             3294
_reflns_number_gt                2274
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1199
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_number_reflns         3294
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+1.0487P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.163
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX2 (Bruker)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker AXS)'
_computing_publication_material  'SHELXTL (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.00716(6) 0.85834(14) 0.07201(8) 0.0636(4) Uani d . . . 1 . .
O O2 -0.01095(6) 0.66500(15) 0.01400(8) 0.0716(5) Uani d . . . 1 . .
N N1 0.14219(6) 0.48669(15) 0.12971(8) 0.0457(4) Uani d . . . 1 . .
N N2 0.15527(7) 0.69973(15) 0.20267(9) 0.0492(4) Uani d . . . 1 . .
C C1 0.04991(10) 1.1566(2) 0.17921(13) 0.0684(6) Uani d . . . 1 . .
H H1 0.0377 1.2468 0.1815 0.082 Uiso calc U . R 1 . .
C C2 0.02058(10) 1.0711(2) 0.12810(12) 0.0632(6) Uani d . . . 1 . .
H H2 -0.0117 1.1024 0.0959 0.076 Uiso calc U . R 1 . .
C C3 0.03977(8) 0.93796(19) 0.12519(11) 0.0496(5) Uani d . . . 1 . .
C C4 0.08832(8) 0.88807(18) 0.17140(10) 0.0452(5) Uani d . . . 1 . .
C C5 0.11678(9) 0.9766(2) 0.22331(11) 0.0566(5) Uani d . . . 1 . .
H H3 0.1491 0.9458 0.2556 0.068 Uiso calc U . R 1 . .
C C6 0.09751(10) 1.1095(2) 0.22733(13) 0.0674(6) Uani d . . . 1 . .
H H4 0.1166 1.1676 0.2626 0.081 Uiso calc U . R 1 . .
C C7 0.10742(8) 0.74594(18) 0.16341(10) 0.0432(4) Uani d . . . 1 . .
C C8 0.07140(7) 0.66753(19) 0.10834(10) 0.0450(5) Uani d . . . 1 . .
C C9 0.02089(8) 0.7232(2) 0.06217(11) 0.0531(5) Uani d . . . 1 . .
C C10 0.09392(8) 0.54032(18) 0.09201(10) 0.0456(5) Uani d . . . 1 . .
H H5 0.0744 0.4909 0.0531 0.055 Uiso calc U . R 1 . .
C C11 0.17157(8) 0.55758(18) 0.19715(10) 0.0463(5) Uani d . . . 1 . .
H H6 0.2171 0.553 0.1924 0.056 Uiso calc U . R 1 . .
C C12 0.15656(8) 0.48038(18) 0.26894(10) 0.0470(5) Uani d . . . 1 . .
C C13 0.20001(9) 0.3932(2) 0.30228(11) 0.0561(5) Uani d . . . 1 . .
H H7 0.2391 0.3837 0.2817 0.067 Uiso calc U . R 1 . .
C C14 0.18618(11) 0.3195(2) 0.36599(12) 0.0677(6) Uani d . . . 1 . .
H H8 0.2158 0.2607 0.3877 0.081 Uiso calc U . R 1 . .
C C15 0.12857(12) 0.3336(2) 0.39706(12) 0.0719(6) Uani d . . . 1 . .
H H9 0.119 0.2838 0.4395 0.086 Uiso calc U . R 1 . .
C C16 0.08525(11) 0.4215(2) 0.36520(13) 0.0711(6) Uani d . . . 1 . .
H H10 0.0465 0.4318 0.3866 0.085 Uiso calc U . R 1 . .
C C17 0.09874(9) 0.4950(2) 0.30139(12) 0.0603(5) Uani d . . . 1 . .
H H11 0.0691 0.5543 0.2802 0.072 Uiso calc U . R 1 . .
C C18 0.17174(8) 0.36053(18) 0.10540(11) 0.0524(5) Uani d . . . 1 . .
H H13 0.1458 0.3197 0.0653 0.063 Uiso calc U . R 1 . .
H H12 0.1742 0.2975 0.1474 0.063 Uiso calc U . R 1 . .
C C19 0.23672(8) 0.38422(19) 0.07759(10) 0.0473(5) Uani d . . . 1 . .
C C20 0.28742(10) 0.3153(2) 0.10816(12) 0.0648(6) Uani d . . . 1 . .
H H14 0.282 0.2542 0.1472 0.078 Uiso calc U . R 1 . .
C C21 0.34662(10) 0.3358(3) 0.08136(14) 0.0794(7) Uani d . . . 1 . .
H H15 0.3807 0.2886 0.1026 0.095 Uiso calc U . R 1 . .
C C22 0.35520(10) 0.4246(3) 0.02429(14) 0.0761(7) Uani d . . . 1 . .
H H16 0.3951 0.4382 0.0066 0.091 Uiso calc U . R 1 . .
C C23 0.30545(11) 0.4936(3) -0.00713(14) 0.0816(7) Uani d . . . 1 . .
H H17 0.3112 0.5542 -0.0463 0.098 Uiso calc U . R 1 . .
C C24 0.24624(10) 0.4731(2) 0.01956(13) 0.0706(6) Uani d . . . 1 . .
H H18 0.2123 0.5201 -0.0021 0.085 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C9 . 1.378(2) ?
O1 C3 . 1.392(2) ?
O2 C9 . 1.214(2) ?
N1 C10 . 1.316(2) ?
N1 C18 . 1.469(2) ?
N1 C11 . 1.500(2) ?
N2 C7 . 1.295(2) ?
N2 C11 . 1.450(2) ?
C1 C2 . 1.371(3) ?
C1 C6 . 1.380(3) ?
C1 H1 . 0.93 ?
C2 C3 . 1.378(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.385(3) ?
C4 C5 . 1.390(2) ?
C4 C7 . 1.469(2) ?
C5 C6 . 1.378(3) ?
C5 H3 . 0.93 ?
C6 H4 . 0.93 ?
C7 C8 . 1.443(2) ?
C8 C10 . 1.380(2) ?
C8 C9 . 1.436(2) ?
C10 H5 . 0.93 ?
C11 C12 . 1.530(3) ?
C11 H6 . 0.98 ?
C12 C13 . 1.380(3) ?
C12 C17 . 1.391(3) ?
C13 C14 . 1.386(3) ?
C13 H7 . 0.93 ?
C14 C15 . 1.376(3) ?
C14 H8 . 0.93 ?
C15 C16 . 1.372(3) ?
C15 H9 . 0.93 ?
C16 C17 . 1.385(3) ?
C16 H10 . 0.93 ?
C17 H11 . 0.93 ?
C18 C19 . 1.510(3) ?
C18 H13 . 0.97 ?
C18 H12 . 0.97 ?
C19 C20 . 1.371(3) ?
C19 C24 . 1.374(3) ?
C20 C21 . 1.384(3) ?
C20 H14 . 0.93 ?
C21 C22 . 1.357(3) ?
C21 H15 . 0.93 ?
C22 C23 . 1.361(3) ?
C22 H16 . 0.93 ?
C23 C24 . 1.383(3) ?
C23 H17 . 0.93 ?
C24 H18 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C3 . . 121.97(15) ?
C10 N1 C18 . . 121.91(15) ?
C10 N1 C11 . . 120.65(14) ?
C18 N1 C11 . . 117.35(14) ?
C7 N2 C11 . . 119.38(14) ?
C2 C1 C6 . . 120.4(2) ?
C2 C1 H1 . . 119.8 ?
C6 C1 H1 . . 119.8 ?
C1 C2 C3 . . 118.9(2) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 122.22(18) ?
C2 C3 O1 . . 115.02(17) ?
C4 C3 O1 . . 122.76(17) ?
C3 C4 C5 . . 117.64(17) ?
C3 C4 C7 . . 119.08(16) ?
C5 C4 C7 . . 123.27(17) ?
C6 C5 C4 . . 120.6(2) ?
C6 C5 H3 . . 119.7 ?
C4 C5 H3 . . 119.7 ?
C5 C6 C1 . . 120.2(2) ?
C5 C6 H4 . . 119.9 ?
C1 C6 H4 . . 119.9 ?
N2 C7 C8 . . 124.14(16) ?
N2 C7 C4 . . 120.01(16) ?
C8 C7 C4 . . 115.81(16) ?
C10 C8 C9 . . 119.24(16) ?
C10 C8 C7 . . 116.73(16) ?
C9 C8 C7 . . 123.18(17) ?
O2 C9 O1 . . 115.56(17) ?
O2 C9 C8 . . 127.26(18) ?
O1 C9 C8 . . 117.17(16) ?
N1 C10 C8 . . 122.13(16) ?
N1 C10 H5 . . 118.9 ?
C8 C10 H5 . . 118.9 ?
N2 C11 N1 . . 114.32(14) ?
N2 C11 C12 . . 111.49(15) ?
N1 C11 C12 . . 109.67(14) ?
N2 C11 H6 . . 107.0 ?
N1 C11 H6 . . 107.0 ?
C12 C11 H6 . . 107.0 ?
C13 C12 C17 . . 118.64(18) ?
C13 C12 C11 . . 120.46(17) ?
C17 C12 C11 . . 120.90(17) ?
C12 C13 C14 . . 120.9(2) ?
C12 C13 H7 . . 119.5 ?
C14 C13 H7 . . 119.5 ?
C15 C14 C13 . . 119.9(2) ?
C15 C14 H8 . . 120.0 ?
C13 C14 H8 . . 120.0 ?
C16 C15 C14 . . 119.8(2) ?
C16 C15 H9 . . 120.1 ?
C14 C15 H9 . . 120.1 ?
C15 C16 C17 . . 120.5(2) ?
C15 C16 H10 . . 119.7 ?
C17 C16 H10 . . 119.7 ?
C16 C17 C12 . . 120.2(2) ?
C16 C17 H11 . . 119.9 ?
C12 C17 H11 . . 119.9 ?
N1 C18 C19 . . 112.12(15) ?
N1 C18 H13 . . 109.2 ?
C19 C18 H13 . . 109.2 ?
N1 C18 H12 . . 109.2 ?
C19 C18 H12 . . 109.2 ?
H13 C18 H12 . . 107.9 ?
C20 C19 C24 . . 118.29(19) ?
C20 C19 C18 . . 120.98(18) ?
C24 C19 C18 . . 120.71(17) ?
C19 C20 C21 . . 120.6(2) ?
C19 C20 H14 . . 119.7 ?
C21 C20 H14 . . 119.7 ?
C22 C21 C20 . . 120.3(2) ?
C22 C21 H15 . . 119.8 ?
C20 C21 H15 . . 119.8 ?
C21 C22 C23 . . 120.1(2) ?
C21 C22 H16 . . 120.0 ?
C23 C22 H16 . . 120.0 ?
C22 C23 C24 . . 119.7(2) ?
C22 C23 H17 . . 120.2 ?
C24 C23 H17 . . 120.2 ?
C19 C24 C23 . . 121.1(2) ?
C19 C24 H18 . . 119.5 ?
C23 C24 H18 . . 119.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.5(3) ?
C1 C2 C3 C4 . . . . -1.0(3) ?
C1 C2 C3 O1 . . . . 179.62(18) ?
C9 O1 C3 C2 . . . . 179.89(17) ?
C9 O1 C3 C4 . . . . 0.5(3) ?
C2 C3 C4 C5 . . . . 1.7(3) ?
O1 C3 C4 C5 . . . . -178.96(16) ?
C2 C3 C4 C7 . . . . -178.12(17) ?
O1 C3 C4 C7 . . . . 1.2(3) ?
C3 C4 C5 C6 . . . . -0.9(3) ?
C7 C4 C5 C6 . . . . 178.90(18) ?
C4 C5 C6 C1 . . . . -0.5(3) ?
C2 C1 C6 C5 . . . . 1.3(3) ?
C11 N2 C7 C8 . . . . -5.7(3) ?
C11 N2 C7 C4 . . . . 176.77(15) ?
C3 C4 C7 N2 . . . . 175.58(16) ?
C5 C4 C7 N2 . . . . -4.2(3) ?
C3 C4 C7 C8 . . . . -2.1(2) ?
C5 C4 C7 C8 . . . . 178.06(16) ?
N2 C7 C8 C10 . . . . -6.7(3) ?
C4 C7 C8 C10 . . . . 170.88(16) ?
N2 C7 C8 C9 . . . . -176.07(17) ?
C4 C7 C8 C9 . . . . 1.5(2) ?
C3 O1 C9 O2 . . . . 179.98(17) ?
C3 O1 C9 C8 . . . . -1.1(3) ?
C10 C8 C9 O2 . . . . 9.7(3) ?
C7 C8 C9 O2 . . . . 178.79(19) ?
C10 C8 C9 O1 . . . . -169.02(16) ?
C7 C8 C9 O1 . . . . 0.1(3) ?
C18 N1 C10 C8 . . . . -170.92(16) ?
C11 N1 C10 C8 . . . . 5.4(3) ?
C9 C8 C10 N1 . . . . 176.39(16) ?
C7 C8 C10 N1 . . . . 6.6(3) ?
C7 N2 C11 N1 . . . . 16.7(2) ?
C7 N2 C11 C12 . . . . -108.36(17) ?
C10 N1 C11 N2 . . . . -17.0(2) ?
C18 N1 C11 N2 . . . . 159.52(15) ?
C10 N1 C11 C12 . . . . 109.10(18) ?
C18 N1 C11 C12 . . . . -74.42(18) ?
N2 C11 C12 C13 . . . . -133.07(17) ?
N1 C11 C12 C13 . . . . 99.28(18) ?
N2 C11 C12 C17 . . . . 47.8(2) ?
N1 C11 C12 C17 . . . . -79.8(2) ?
C17 C12 C13 C14 . . . . 1.2(3) ?
C11 C12 C13 C14 . . . . -177.98(17) ?
C12 C13 C14 C15 . . . . -0.4(3) ?
C13 C14 C15 C16 . . . . -0.6(3) ?
C14 C15 C16 C17 . . . . 0.8(3) ?
C15 C16 C17 C12 . . . . 0.0(3) ?
C13 C12 C17 C16 . . . . -1.0(3) ?
C11 C12 C17 C16 . . . . 178.19(17) ?
C10 N1 C18 C19 . . . . 111.10(19) ?
C11 N1 C18 C19 . . . . -65.3(2) ?
N1 C18 C19 C20 . . . . 124.73(19) ?
N1 C18 C19 C24 . . . . -57.0(2) ?
C24 C19 C20 C21 . . . . 0.5(3) ?
C18 C19 C20 C21 . . . . 178.79(19) ?
C19 C20 C21 C22 . . . . -0.1(4) ?
C20 C21 C22 C23 . . . . -0.2(4) ?
C21 C22 C23 C24 . . . . 0.2(4) ?
C20 C19 C24 C23 . . . . -0.5(3) ?
C18 C19 C24 C23 . . . . -178.9(2) ?
C22 C23 C24 C19 . . . . 0.2(4) ?

