# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_KA
_database_code_depnum_ccdc_archive 'CCDC 1503214'
_audit_update_record             
;
2016-09-07 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 N2 O2'
_chemical_formula_sum            'C24 H20 N2 O2'
_chemical_formula_weight         368.42

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.7029(5)
_cell_length_b                   5.8234(2)
_cell_length_c                   22.2875(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.2178(17)
_cell_angle_gamma                90
_cell_volume                     1801.93(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4019
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      25.99

_exptl_crystal_description       Block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13725
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.467
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3172
_reflns_number_gt                2392
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0474P)²+0.4022P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0110(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3172
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0872
_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_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 -0.03731(12) 1.3493(3) 0.07893(8) 0.0385(4) Uani 1 1 d . . . . .
H1 H -0.0320 1.4690 0.0526 0.046 Uiso 1 1 calc R U . . .
C2 C -0.10762(12) 1.3524(3) 0.10583(8) 0.0396(4) Uani 1 1 d . . . . .
H2 H -0.1515 1.4730 0.0974 0.048 Uiso 1 1 calc R U . . .
C3 C -0.11419(11) 1.1733(3) 0.14651(7) 0.0340(4) Uani 1 1 d . . . . .
C4 C -0.18278(12) 1.1687(3) 0.17835(8) 0.0424(4) Uani 1 1 d . . . . .
H4 H -0.2273 1.2873 0.1722 0.051 Uiso 1 1 calc R U . . .
C5 C -0.18412(12) 0.9921(3) 0.21786(8) 0.0439(4) Uani 1 1 d . . . . .
H5 H -0.2293 0.9912 0.2389 0.053 Uiso 1 1 calc R U . . .
C6 C -0.11815(12) 0.8118(3) 0.22721(8) 0.0440(4) Uani 1 1 d . . . . .
H6 H -0.1202 0.6912 0.2541 0.053 Uiso 1 1 calc R U . . .
C7 C -0.05071(11) 0.8112(3) 0.19720(8) 0.0388(4) Uani 1 1 d . . . . .
H7 H -0.0070 0.6906 0.2039 0.047 Uiso 1 1 calc R U . . .
C8 C -0.04712(11) 0.9921(2) 0.15629(7) 0.0318(4) Uani 1 1 d . . . . .
N1 N 0.02293(9) 0.9891(2) 0.12755(6) 0.0323(3) Uani 1 1 d . . . . .
C10 C 0.02786(10) 1.1634(2) 0.09107(7) 0.0301(4) Uani 1 1 d . . . . .
C11 C 0.10366(10) 1.1630(2) 0.05926(7) 0.0317(4) Uani 1 1 d . . . . .
H11A H 0.1325 1.3146 0.0641 0.038 Uiso 1 1 calc R U . . .
H11B H 0.0719 1.1377 0.0142 0.038 Uiso 1 1 calc R U . . .
C12 C 0.18463(11) 0.9871(2) 0.08288(7) 0.0304(4) Uani 1 1 d . . . . .
C13 C 0.24999(11) 1.0513(3) 0.15089(7) 0.0309(4) Uani 1 1 d . . . . .
C14 C 0.36093(10) 0.8629(2) 0.24815(7) 0.0312(4) Uani 1 1 d . . . . .
C15 C 0.41725(11) 0.6677(3) 0.26458(8) 0.0371(4) Uani 1 1 d . . . . .
H15 H 0.4080 0.5469 0.2359 0.045 Uiso 1 1 calc R U . . .
C16 C 0.48729(12) 0.6525(3) 0.32362(8) 0.0436(4) Uani 1 1 d . . . . .
H16 H 0.5249 0.5208 0.3346 0.052 Uiso 1 1 calc R U . . .
C17 C 0.50178(12) 0.8302(3) 0.36609(8) 0.0470(5) Uani 1 1 d . . . . .
H17 H 0.5494 0.8198 0.4057 0.056 Uiso 1 1 calc R U . . .
C18 C 0.44561(13) 1.0239(3) 0.34987(8) 0.0465(4) Uani 1 1 d . . . . .
H18 H 0.4552 1.1442 0.3787 0.056 Uiso 1 1 calc R U . . .
C19 C 0.37479(12) 1.0419(3) 0.29086(8) 0.0403(4) Uani 1 1 d . . . . .
H19 H 0.3370 1.1733 0.2801 0.048 Uiso 1 1 calc R U . . .
C20 C 0.24886(11) 0.9819(3) 0.04105(7) 0.0324(4) Uani 1 1 d . . . . .
C21 C 0.30538(12) 0.7905(3) 0.04171(8) 0.0451(4) Uani 1 1 d . . . . .
H21 H 0.3038 0.6662 0.0676 0.054 Uiso 1 1 calc R U . . .
C22 C 0.36401(13) 0.7828(3) 0.00431(9) 0.0541(5) Uani 1 1 d . . . . .
H22 H 0.4015 0.6534 0.0053 0.065 Uiso 1 1 calc R U . . .
C23 C 0.36733(13) 0.9642(3) -0.03423(9) 0.0516(5) Uani 1 1 d . . . . .
H23 H 0.4064 0.9577 -0.0596 0.062 Uiso 1 1 calc R U . . .
C24 C 0.31250(13) 1.1549(3) -0.03496(9) 0.0512(5) Uani 1 1 d . . . . .
H24 H 0.3144 1.2787 -0.0609 0.061 Uiso 1 1 calc R U . . .
C25 C 0.25425(12) 1.1638(3) 0.00272(8) 0.0425(4) Uani 1 1 d . . . . .
H25 H 0.2180 1.2951 0.0022 0.051 Uiso 1 1 calc R U . . .
N2 N 0.28886(9) 0.8672(2) 0.18732(6) 0.0354(3) Uani 1 1 d . . . . .
O1 O 0.14694(8) 0.76047(16) 0.08226(5) 0.0363(3) Uani 1 1 d . . . . .
O2 O 0.26702(8) 1.25125(18) 0.16703(5) 0.0431(3) Uani 1 1 d . . . . .
H1N H 0.2699(11) 0.734(3) 0.1691(8) 0.038(5) Uiso 1 1 d . . . . .
H1O H 0.1059(16) 0.777(4) 0.1027(10) 0.078(7) Uiso 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 1.355(2) . ?
C1 C10 1.412(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.406(2) . ?
C2 H2 0.9300 . ?
C3 C8 1.412(2) . ?
C3 C4 1.412(2) . ?
C4 C5 1.358(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.366(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.405(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.3806(19) . ?
N1 C10 1.3171(18) . ?
C10 C11 1.505(2) . ?
C11 C12 1.527(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.4295(17) . ?
C12 C20 1.530(2) . ?
C12 C13 1.550(2) . ?
C13 O2 1.2201(17) . ?
C13 N2 1.353(2) . ?
C14 C19 1.381(2) . ?
C14 C15 1.383(2) . ?
C14 N2 1.420(2) . ?
C15 C16 1.381(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.379(2) . ?
C20 C21 1.387(2) . ?
C21 C22 1.383(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.372(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N2 H1N 0.879(17) . ?
O1 H1O 0.87(2) . ?

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
C2 C1 C10 119.59(14) . . ?
C2 C1 H1 120.2 . . ?
C10 C1 H1 120.2 . . ?
C1 C2 C3 119.99(14) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C8 117.49(14) . . ?
C2 C3 C4 123.40(14) . . ?
C8 C3 C4 119.10(14) . . ?
C5 C4 C3 120.38(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.54(15) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 120.57(15) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.26(15) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N1 C8 C7 119.00(13) . . ?
N1 C8 C3 121.84(13) . . ?
C7 C8 C3 119.16(14) . . ?
C10 N1 C8 118.54(12) . . ?
N1 C10 C1 122.51(14) . . ?
N1 C10 C11 119.30(13) . . ?
C1 C10 C11 118.16(13) . . ?
C10 C11 C12 116.93(12) . . ?
C10 C11 H11A 108.1 . . ?
C12 C11 H11A 108.1 . . ?
C10 C11 H11B 108.1 . . ?
C12 C11 H11B 108.1 . . ?
H11A C11 H11B 107.3 . . ?
O1 C12 C11 111.11(12) . . ?
O1 C12 C20 106.93(11) . . ?
C11 C12 C20 111.76(12) . . ?
O1 C12 C13 110.23(12) . . ?
C11 C12 C13 109.72(12) . . ?
C20 C12 C13 106.99(12) . . ?
O2 C13 N2 125.05(14) . . ?
O2 C13 C12 121.31(13) . . ?
N2 C13 C12 113.53(13) . . ?
C19 C14 C15 119.89(15) . . ?
C19 C14 N2 122.64(14) . . ?
C15 C14 N2 117.45(14) . . ?
C16 C15 C14 119.92(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 120.45(15) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.65(16) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 120.66(16) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 119.42(15) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C25 C20 C21 117.84(15) . . ?
C25 C20 C12 122.36(13) . . ?
C21 C20 C12 119.79(13) . . ?
C22 C21 C20 120.64(16) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.64(17) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 119.31(17) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.19(17) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 121.36(16) . . ?
C20 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C13 N2 C14 128.47(14) . . ?
C13 N2 H1N 114.6(11) . . ?
C14 N2 H1N 116.7(11) . . ?
C12 O1 H1O 102.9(14) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C8 -1.6(2) . . . . ?
C1 C2 C3 C4 177.33(16) . . . . ?
C2 C3 C4 C5 -178.89(16) . . . . ?
C8 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 N1 178.79(14) . . . . ?
C6 C7 C8 C3 -0.2(2) . . . . ?
C2 C3 C8 N1 0.3(2) . . . . ?
C4 C3 C8 N1 -178.65(14) . . . . ?
C2 C3 C8 C7 179.29(14) . . . . ?
C4 C3 C8 C7 0.3(2) . . . . ?
C7 C8 N1 C10 -177.63(14) . . . . ?
C3 C8 N1 C10 1.4(2) . . . . ?
C8 N1 C10 C1 -1.8(2) . . . . ?
C8 N1 C10 C11 -179.91(12) . . . . ?
C2 C1 C10 N1 0.5(2) . . . . ?
C2 C1 C10 C11 178.66(14) . . . . ?
N1 C10 C11 C12 -13.4(2) . . . . ?
C1 C10 C11 C12 168.37(13) . . . . ?
C10 C11 C12 O1 52.87(17) . . . . ?
C10 C11 C12 C20 172.22(12) . . . . ?
C10 C11 C12 C13 -69.28(16) . . . . ?
O1 C12 C13 O2 -158.39(13) . . . . ?
C11 C12 C13 O2 -35.72(19) . . . . ?
C20 C12 C13 O2 85.70(16) . . . . ?
O1 C12 C13 N2 25.25(17) . . . . ?
C11 C12 C13 N2 147.92(12) . . . . ?
C20 C12 C13 N2 -90.66(14) . . . . ?
C19 C14 C15 C16 -0.1(2) . . . . ?
N2 C14 C15 C16 -178.82(14) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C15 C14 C19 C18 0.3(2) . . . . ?
N2 C14 C19 C18 178.92(14) . . . . ?
C17 C18 C19 C14 0.0(2) . . . . ?
O1 C12 C20 C25 143.33(15) . . . . ?
C11 C12 C20 C25 21.5(2) . . . . ?
C13 C12 C20 C25 -98.58(17) . . . . ?
O1 C12 C20 C21 -37.67(18) . . . . ?
C11 C12 C20 C21 -159.47(14) . . . . ?
C13 C12 C20 C21 80.42(16) . . . . ?
C25 C20 C21 C22 -0.9(2) . . . . ?
C12 C20 C21 C22 -179.91(16) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C21 C20 C25 C24 1.3(2) . . . . ?
C12 C20 C25 C24 -179.67(15) . . . . ?
C23 C24 C25 C20 -0.8(3) . . . . ?
O2 C13 N2 C14 -5.2(3) . . . . ?
C12 C13 N2 C14 170.97(13) . . . . ?
C19 C14 N2 C13 27.9(2) . . . . ?
C15 C14 N2 C13 -153.44(15) . . . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_3ac
_database_code_depnum_ccdc_archive 'CCDC 1503215'
_audit_update_record             
;
2016-09-07 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N2 O3'
_chemical_formula_weight         410.45

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                   10.6354(7)
_cell_length_b                   10.7608(7)
_cell_length_c                   11.0786(7)
_cell_angle_alpha                66.546(3)
_cell_angle_beta                 66.529(2)
_cell_angle_gamma                84.182(3)
_cell_volume                     1064.45(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8056
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      26.86

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17160
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         26.950
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4569
_reflns_number_gt                3565
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0533P)²+0.2195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4569
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1160
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.18017(14) -0.11555(13) 0.47656(15) 0.0448(3) Uani 1 1 d . . . . .
C2 C 0.15401(16) -0.17012(16) 0.62352(16) 0.0569(4) Uani 1 1 d . . . . .
H2 H 0.2207 -0.1596 0.6539 0.068 Uiso 1 1 calc R U . . .
C3 C 0.03104(18) -0.23830(17) 0.72116(19) 0.0678(5) Uani 1 1 d . . . . .
H3 H 0.0146 -0.2746 0.8180 0.081 Uiso 1 1 calc R U . . .
C4 C -0.07037(18) -0.25439(17) 0.6778(2) 0.0707(5) Uani 1 1 d . . . . .
H4 H -0.1540 -0.3007 0.7459 0.085 Uiso 1 1 calc R U . . .
C5 C -0.04798(17) -0.20277(17) 0.5364(2) 0.0665(5) Uani 1 1 d . . . . .
H5 H -0.1164 -0.2144 0.5088 0.080 Uiso 1 1 calc R U . . .
C6 C 0.07855(15) -0.13160(14) 0.43115(17) 0.0505(3) Uani 1 1 d . . . . .
C7 C 0.10951(16) -0.07406(16) 0.28345(18) 0.0582(4) Uani 1 1 d . . . . .
H7 H 0.0451 -0.0829 0.2496 0.070 Uiso 1 1 calc R U . . .
C8 C 0.23286(15) -0.00566(16) 0.18988(16) 0.0518(4) Uani 1 1 d . . . . .
H8 H 0.2530 0.0334 0.0922 0.062 Uiso 1 1 calc R U . . .
C9 C 0.33009(13) 0.00536(13) 0.24288(14) 0.0404(3) Uani 1 1 d . . . . .
C10 C 0.46972(13) 0.07581(14) 0.14099(13) 0.0411(3) Uani 1 1 d . . . . .
H10A H 0.4602 0.1489 0.0591 0.049 Uiso 1 1 calc R U . . .
H10B H 0.5281 0.0116 0.1067 0.049 Uiso 1 1 calc R U . . .
C11 C 0.54248(13) 0.13517(12) 0.20387(12) 0.0370(3) Uani 1 1 d . . . . .
C12 C 0.46081(13) 0.25062(13) 0.24323(13) 0.0377(3) Uani 1 1 d . . . . .
C13 C 0.39439(13) 0.34122(13) 0.43468(14) 0.0398(3) Uani 1 1 d . . . . .
C14 C 0.34872(16) 0.46426(15) 0.36716(16) 0.0536(4) Uani 1 1 d . . . . .
H14 H 0.3543 0.4894 0.2745 0.064 Uiso 1 1 calc R U . . .
C15 C 0.29480(19) 0.54926(17) 0.43922(19) 0.0650(4) Uani 1 1 d . . . . .
H15 H 0.2632 0.6315 0.3944 0.078 Uiso 1 1 calc R U . . .
C16 C 0.28694(16) 0.51450(15) 0.57605(17) 0.0561(4) Uani 1 1 d . . . . .
H16 H 0.2511 0.5732 0.6226 0.067 Uiso 1 1 calc R U . . .
C17 C 0.33254(14) 0.39213(13) 0.64372(14) 0.0448(3) Uani 1 1 d . . . . .
C18 C 0.38526(14) 0.30581(13) 0.57250(14) 0.0434(3) Uani 1 1 d . . . . .
H18 H 0.4150 0.2228 0.6182 0.052 Uiso 1 1 calc R U . . .
C19 C 0.32793(18) 0.34760(17) 0.79193(16) 0.0604(4) Uani 1 1 d . . . . .
C20 C 0.2813(2) 0.4409(2) 0.86970(19) 0.0764(5) Uani 1 1 d . . . . .
H20A H 0.1855 0.4541 0.8904 0.115 Uiso 1 1 calc R U . . .
H20B H 0.3333 0.5268 0.8111 0.115 Uiso 1 1 calc R U . . .
H20C H 0.2952 0.4017 0.9575 0.115 Uiso 1 1 calc R U . . .
C21 C 0.68710(13) 0.19157(13) 0.09185(13) 0.0399(3) Uani 1 1 d . . . . .
C22 C 0.70815(16) 0.31437(16) -0.02375(16) 0.0565(4) Uani 1 1 d . . . . .
H22 H 0.6339 0.3659 -0.0314 0.068 Uiso 1 1 calc R U . . .
C23 C 0.83834(17) 0.36077(18) -0.12768(19) 0.0677(5) Uani 1 1 d . . . . .
H23 H 0.8509 0.4427 -0.2054 0.081 Uiso 1 1 calc R U . . .
C24 C 0.94905(17) 0.2872(2) -0.11729(19) 0.0666(5) Uani 1 1 d . . . . .
H24 H 1.0367 0.3193 -0.1870 0.080 Uiso 1 1 calc R U . . .
C25 C 0.92969(17) 0.1661(2) -0.0036(2) 0.0709(5) Uani 1 1 d . . . . .
H25 H 1.0047 0.1159 0.0039 0.085 Uiso 1 1 calc R U . . .
C26 C 0.79965(15) 0.11761(17) 0.10033(17) 0.0568(4) Uani 1 1 d . . . . .
H26 H 0.7878 0.0346 0.1766 0.068 Uiso 1 1 calc R U . . .
N1 N 0.30501(11) -0.04815(11) 0.38068(11) 0.0435(3) Uani 1 1 d . . . . .
N2 N 0.45494(12) 0.25014(12) 0.36763(12) 0.0448(3) Uani 1 1 d . . . . .
O1 O 0.55496(10) 0.03195(9) 0.32796(10) 0.0430(2) Uani 1 1 d . . . . .
O2 O 0.41087(10) 0.33427(10) 0.16547(10) 0.0505(3) Uani 1 1 d . . . . .
O3 O 0.3621(2) 0.23655(15) 0.84855(14) 0.1089(6) Uani 1 1 d . . . . .
H1N H 0.4859(16) 0.1782(17) 0.4147(17) 0.053(4) Uiso 1 1 d . . . . .
H1O H 0.4733(18) -0.0129(18) 0.3759(19) 0.066(5) Uiso 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 1.3696(17) . ?
C1 C2 1.409(2) . ?
C1 C6 1.411(2) . ?
C2 C3 1.362(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.416(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(2) . ?
C7 C8 1.357(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.4114(19) . ?
C8 H8 0.9300 . ?
C9 N1 1.3191(17) . ?
C9 C10 1.5053(18) . ?
C10 C11 1.5415(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O1 1.4287(14) . ?
C11 C21 1.5308(18) . ?
C11 C12 1.5487(17) . ?
C12 O2 1.2185(15) . ?
C12 N2 1.3525(16) . ?
C13 C18 1.3828(18) . ?
C13 C14 1.3854(18) . ?
C13 N2 1.4134(16) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.3875(18) . ?
C17 C19 1.497(2) . ?
C18 H18 0.9300 . ?
C19 O3 1.204(2) . ?
C19 C20 1.498(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.3827(19) . ?
C21 C22 1.386(2) . ?
C22 C23 1.380(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.367(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.382(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N2 H1N 0.862(16) . ?
O1 H1O 0.884(18) . ?

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 118.73(13) . . ?
N1 C1 C6 121.49(13) . . ?
C2 C1 C6 119.78(13) . . ?
C3 C2 C1 119.97(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.83(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.51(16) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.60(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C1 117.43(13) . . ?
C7 C6 C5 124.24(15) . . ?
C1 C6 C5 118.32(15) . . ?
C8 C7 C6 120.39(14) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.08(14) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
N1 C9 C8 122.21(13) . . ?
N1 C9 C10 117.63(11) . . ?
C8 C9 C10 120.12(12) . . ?
C9 C10 C11 115.25(10) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
O1 C11 C21 108.22(10) . . ?
O1 C11 C10 110.59(10) . . ?
C21 C11 C10 108.72(10) . . ?
O1 C11 C12 109.73(9) . . ?
C21 C11 C12 109.59(10) . . ?
C10 C11 C12 109.96(10) . . ?
O2 C12 N2 124.72(12) . . ?
O2 C12 C11 121.78(11) . . ?
N2 C12 C11 113.47(10) . . ?
C18 C13 C14 119.46(12) . . ?
C18 C13 N2 117.46(11) . . ?
C14 C13 N2 123.05(12) . . ?
C15 C14 C13 119.22(13) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 121.30(14) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 119.72(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 119.20(13) . . ?
C16 C17 C19 122.82(13) . . ?
C18 C17 C19 117.99(13) . . ?
C13 C18 C17 121.10(12) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
O3 C19 C17 119.86(14) . . ?
O3 C19 C20 119.96(15) . . ?
C17 C19 C20 120.18(15) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.31(13) . . ?
C26 C21 C11 120.45(12) . . ?
C22 C21 C11 121.17(12) . . ?
C23 C22 C21 120.54(15) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.55(16) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 119.46(15) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.60(16) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.53(15) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C9 N1 C1 119.38(12) . . ?
C12 N2 C13 129.55(11) . . ?
C12 N2 H1N 112.7(11) . . ?
C13 N2 H1N 117.4(11) . . ?
C11 O1 H1O 103.5(11) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.63(13) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
N1 C1 C6 C7 -0.85(19) . . . . ?
C2 C1 C6 C7 179.41(13) . . . . ?
N1 C1 C6 C5 179.86(12) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C4 C5 C6 C7 -179.34(15) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C1 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 C8 179.02(15) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
C7 C8 C9 N1 -0.3(2) . . . . ?
C7 C8 C9 C10 177.54(13) . . . . ?
N1 C9 C10 C11 -26.81(16) . . . . ?
C8 C9 C10 C11 155.24(12) . . . . ?
C9 C10 C11 O1 56.34(14) . . . . ?
C9 C10 C11 C21 175.02(10) . . . . ?
C9 C10 C11 C12 -64.99(14) . . . . ?
O1 C11 C12 O2 -163.58(12) . . . . ?
C21 C11 C12 O2 77.73(14) . . . . ?
C10 C11 C12 O2 -41.73(16) . . . . ?
O1 C11 C12 N2 18.15(15) . . . . ?
C21 C11 C12 N2 -100.54(12) . . . . ?
C10 C11 C12 N2 140.00(11) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
N2 C13 C14 C15 -177.89(14) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C15 C16 C17 C19 179.72(15) . . . . ?
C14 C13 C18 C17 -0.7(2) . . . . ?
N2 C13 C18 C17 177.26(12) . . . . ?
C16 C17 C18 C13 0.8(2) . . . . ?
C19 C17 C18 C13 -179.10(13) . . . . ?
C16 C17 C19 O3 175.91(18) . . . . ?
C18 C17 C19 O3 -4.2(2) . . . . ?
C16 C17 C19 C20 -4.2(2) . . . . ?
C18 C17 C19 C20 175.69(15) . . . . ?
O1 C11 C21 C26 19.70(16) . . . . ?
C10 C11 C21 C26 -100.47(14) . . . . ?
C12 C11 C21 C26 139.32(13) . . . . ?
O1 C11 C21 C22 -163.32(12) . . . . ?
C10 C11 C21 C22 76.52(15) . . . . ?
C12 C11 C21 C22 -43.69(16) . . . . ?
C26 C21 C22 C23 0.3(2) . . . . ?
C11 C21 C22 C23 -176.78(14) . . . . ?
C21 C22 C23 C24 -0.9(3) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
C22 C21 C26 C25 0.5(2) . . . . ?
C11 C21 C26 C25 177.60(14) . . . . ?
C24 C25 C26 C21 -0.7(3) . . . . ?
C8 C9 N1 C1 -0.75(19) . . . . ?
C10 C9 N1 C1 -178.65(11) . . . . ?
C2 C1 N1 C9 -178.92(12) . . . . ?
C6 C1 N1 C9 1.33(18) . . . . ?
O2 C12 N2 C13 -0.6(2) . . . . ?
C11 C12 N2 C13 177.62(12) . . . . ?
C18 C13 N2 C12 170.56(13) . . . . ?
C14 C13 N2 C12 -11.5(2) . . . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.036

