# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_SPA143
_database_code_depnum_ccdc_archive 'CCDC 1579626'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2017-12-26 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         'C25 H21 N3 O3'
_chemical_formula_sum            'C25 H21 N3 O3'
_chemical_formula_weight         411.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   34.885(7)
_cell_length_b                   6.4970(13)
_cell_length_c                   18.207(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.73(3)
_cell_angle_gamma                90
_cell_volume                     4112.5(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    46460
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14671
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4167
_reflns_number_gt                2933
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.5.1'
_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)+(0.0812P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0091(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4167
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
O1 O 0.34640(3) 0.34154(19) 0.31017(7) 0.0385(3) Uani 1 1 d . . . . .
O2 O 0.25999(4) -0.17478(18) 0.28157(6) 0.0363(3) Uani 1 1 d . . . . .
O3 O 0.22913(3) 0.3597(2) 0.42307(7) 0.0378(3) Uani 1 1 d . . . . .
N1 N 0.41331(4) 1.1427(2) 0.49764(7) 0.0323(4) Uani 1 1 d . . . . .
N2 N 0.30431(4) 0.0786(2) 0.30006(7) 0.0245(3) Uani 1 1 d . . . . .
N3 N 0.24672(4) 0.0808(2) 0.36010(7) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.44413(5) 1.2010(2) 0.45506(9) 0.0267(4) Uani 1 1 d . . . . .
C2 C 0.43760(5) 1.2358(3) 0.38027(9) 0.0361(4) Uani 1 1 d . . . . .
H2 H 0.4125 1.2190 0.3564 0.043 Uiso 1 1 calc R U . . .
C3 C 0.46788(5) 1.2956(3) 0.34014(10) 0.0436(5) Uani 1 1 d . . . . .
H3 H 0.4635 1.3169 0.2885 0.052 Uiso 1 1 calc R U . . .
C4 C 0.50432(5) 1.3244(3) 0.37444(10) 0.0391(5) Uani 1 1 d . . . . .
H4 H 0.5248 1.3670 0.3467 0.047 Uiso 1 1 calc R U . . .
C5 C 0.51058(5) 1.2910(3) 0.44902(10) 0.0333(4) Uani 1 1 d . . . . .
H5 H 0.5356 1.3101 0.4729 0.040 Uiso 1 1 calc R U . . .
C6 C 0.48064(5) 1.2296(3) 0.48958(9) 0.0299(4) Uani 1 1 d . . . . .
H6 H 0.4852 1.2071 0.5411 0.036 Uiso 1 1 calc R U . . .
C7 C 0.41104(4) 1.2369(3) 0.56838(8) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.42221(6) 1.1263(3) 0.63144(10) 0.0396(5) Uani 1 1 d . . . . .
H8 H 0.4321 0.9907 0.6278 0.048 Uiso 1 1 calc R U . . .
C9 C 0.41895(6) 1.2147(4) 0.70002(10) 0.0526(6) Uani 1 1 d . . . . .
H9 H 0.4269 1.1394 0.7434 0.063 Uiso 1 1 calc R U . . .
C10 C 0.40448(6) 1.4085(4) 0.70576(11) 0.0519(6) Uani 1 1 d . . . . .
H10 H 0.4019 1.4669 0.7529 0.062 Uiso 1 1 calc R U . . .
C11 C 0.39368(5) 1.5190(3) 0.64320(12) 0.0467(5) Uani 1 1 d . . . . .
H11 H 0.3838 1.6544 0.6473 0.056 Uiso 1 1 calc R U . . .
C12 C 0.39705(5) 1.4347(3) 0.57407(10) 0.0355(4) Uani 1 1 d . . . . .
H12 H 0.3898 1.5124 0.5309 0.043 Uiso 1 1 calc R U . . .
C13 C 0.38562(5) 0.9972(3) 0.47391(8) 0.0265(4) Uani 1 1 d . . . . .
C14 C 0.34961(5) 0.9966(3) 0.50310(9) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.3439 1.0978 0.5382 0.034 Uiso 1 1 calc R U . . .
C15 C 0.32266(5) 0.8502(3) 0.48104(8) 0.0258(4) Uani 1 1 d . . . . .
H15 H 0.2983 0.8548 0.5008 0.031 Uiso 1 1 calc R U . . .
C16 C 0.32967(4) 0.6942(2) 0.43052(8) 0.0235(4) Uani 1 1 d . . . . .
C17 C 0.36580(4) 0.6966(3) 0.40119(8) 0.0273(4) Uani 1 1 d . . . . .
H17 H 0.3716 0.5945 0.3664 0.033 Uiso 1 1 calc R U . . .
C18 C 0.39287(5) 0.8446(3) 0.42207(9) 0.0293(4) Uani 1 1 d . . . . .
H18 H 0.4169 0.8434 0.4010 0.035 Uiso 1 1 calc R U . . .
C19 C 0.29885(4) 0.5455(2) 0.41674(8) 0.0238(4) Uani 1 1 d . . . . .
H19 H 0.2772 0.5840 0.4421 0.029 Uiso 1 1 calc R U . . .
C20 C 0.29148(4) 0.3684(2) 0.37876(8) 0.0224(4) Uani 1 1 d . . . . .
C21 C 0.25368(4) 0.2752(3) 0.38935(8) 0.0256(4) Uani 1 1 d . . . . .
C22 C 0.26967(4) -0.0143(3) 0.31172(8) 0.0260(4) Uani 1 1 d . . . . .
C23 C 0.31645(4) 0.2680(2) 0.32844(8) 0.0246(4) Uani 1 1 d . . . . .
C24 C 0.32742(5) -0.0227(3) 0.24689(9) 0.0356(4) Uani 1 1 d . . . . .
H24A H 0.3161 0.0043 0.1968 0.053 Uiso 1 1 calc R U . . .
H24B H 0.3279 -0.1714 0.2560 0.053 Uiso 1 1 calc R U . . .
H24C H 0.3537 0.0311 0.2524 0.053 Uiso 1 1 calc R U . . .
C25 C 0.20956(5) -0.0170(3) 0.36904(10) 0.0377(5) Uani 1 1 d . . . . .
H25A H 0.1985 0.0409 0.4123 0.057 Uiso 1 1 calc R U . . .
H25B H 0.2132 -0.1656 0.3758 0.057 Uiso 1 1 calc R U . . .
H25C H 0.1921 0.0082 0.3250 0.057 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 C23 1.2197(19) . ?
O2 C22 1.2133(19) . ?
O3 C21 1.2243(19) . ?
N1 C13 1.394(2) . ?
N1 C1 1.428(2) . ?
N1 C7 1.434(2) . ?
N2 C22 1.383(2) . ?
N2 C23 1.387(2) . ?
N2 C24 1.466(2) . ?
N3 C22 1.384(2) . ?
N3 C21 1.384(2) . ?
N3 C25 1.465(2) . ?
C1 C2 1.381(2) . ?
C1 C6 1.385(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.382(3) . ?
C7 C8 1.383(2) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.364(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.404(2) . ?
C13 C18 1.406(2) . ?
C14 C15 1.374(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.409(2) . ?
C16 C19 1.452(2) . ?
C17 C18 1.379(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.356(2) . ?
C19 H19 0.9500 . ?
C20 C23 1.468(2) . ?
C20 C21 1.478(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C13 N1 C1 123.02(13) . . ?
C13 N1 C7 118.66(13) . . ?
C1 N1 C7 118.31(13) . . ?
C22 N2 C23 125.03(13) . . ?
C22 N2 C24 116.13(14) . . ?
C23 N2 C24 118.47(13) . . ?
C22 N3 C21 124.04(13) . . ?
C22 N3 C25 116.17(14) . . ?
C21 N3 C25 118.79(14) . . ?
C2 C1 C6 119.75(15) . . ?
C2 C1 N1 120.57(15) . . ?
C6 C1 N1 119.64(15) . . ?
C1 C2 C3 119.61(17) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 120.76(18) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.35(16) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.41(17) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.11(16) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C12 C7 C8 119.86(16) . . ?
C12 C7 N1 120.68(15) . . ?
C8 C7 N1 119.45(16) . . ?
C7 C8 C9 119.61(19) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.82(18) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C7 C12 C11 119.48(18) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N1 C13 C14 120.21(14) . . ?
N1 C13 C18 121.85(14) . . ?
C14 C13 C18 117.92(15) . . ?
C15 C14 C13 120.22(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 122.66(15) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C15 C16 C17 116.73(14) . . ?
C15 C16 C19 115.30(14) . . ?
C17 C16 C19 127.94(15) . . ?
C18 C17 C16 121.13(15) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 121.31(15) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?
C20 C19 C16 139.39(15) . . ?
C20 C19 H19 110.3 . . ?
C16 C19 H19 110.3 . . ?
C19 C20 C23 126.73(14) . . ?
C19 C20 C21 114.50(14) . . ?
C23 C20 C21 118.75(14) . . ?
O3 C21 N3 119.64(14) . . ?
O3 C21 C20 123.38(15) . . ?
N3 C21 C20 116.98(14) . . ?
O2 C22 N2 121.33(15) . . ?
O2 C22 N3 121.16(15) . . ?
N2 C22 N3 117.50(14) . . ?
O1 C23 N2 119.21(14) . . ?
O1 C23 C20 124.18(15) . . ?
N2 C23 C20 116.61(13) . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C2 43.3(2) . . . . ?
C7 N1 C1 C2 -137.39(17) . . . . ?
C13 N1 C1 C6 -138.92(18) . . . . ?
C7 N1 C1 C6 40.4(2) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
N1 C1 C2 C3 178.97(18) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
N1 C1 C6 C5 -178.45(16) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C13 N1 C7 C12 -102.96(19) . . . . ?
C1 N1 C7 C12 77.7(2) . . . . ?
C13 N1 C7 C8 75.6(2) . . . . ?
C1 N1 C7 C8 -103.75(19) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
N1 C7 C8 C9 -178.02(16) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C8 C7 C12 C11 -1.2(2) . . . . ?
N1 C7 C12 C11 177.34(15) . . . . ?
C10 C11 C12 C7 0.7(3) . . . . ?
C1 N1 C13 C14 -157.55(16) . . . . ?
C7 N1 C13 C14 23.1(2) . . . . ?
C1 N1 C13 C18 24.1(3) . . . . ?
C7 N1 C13 C18 -155.26(16) . . . . ?
N1 C13 C14 C15 -178.43(15) . . . . ?
C18 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C16 1.3(3) . . . . ?
C14 C15 C16 C17 -1.6(2) . . . . ?
C14 C15 C16 C19 176.52(15) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C19 C16 C17 C18 -177.26(15) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
N1 C13 C18 C17 177.42(16) . . . . ?
C14 C13 C18 C17 -1.0(2) . . . . ?
C15 C16 C19 C20 -175.49(18) . . . . ?
C17 C16 C19 C20 2.4(3) . . . . ?
C16 C19 C20 C23 -5.0(3) . . . . ?
C16 C19 C20 C21 176.63(18) . . . . ?
C22 N3 C21 O3 169.47(15) . . . . ?
C25 N3 C21 O3 1.3(2) . . . . ?
C22 N3 C21 C20 -11.6(2) . . . . ?
C25 N3 C21 C20 -179.74(14) . . . . ?
C19 C20 C21 O3 7.4(2) . . . . ?
C23 C20 C21 O3 -171.09(15) . . . . ?
C19 C20 C21 N3 -171.50(13) . . . . ?
C23 C20 C21 N3 10.0(2) . . . . ?
C23 N2 C22 O2 175.63(14) . . . . ?
C24 N2 C22 O2 2.8(2) . . . . ?
C23 N2 C22 N3 -5.5(2) . . . . ?
C24 N2 C22 N3 -178.29(14) . . . . ?
C21 N3 C22 O2 -171.85(14) . . . . ?
C25 N3 C22 O2 -3.4(2) . . . . ?
C21 N3 C22 N2 9.2(2) . . . . ?
C25 N3 C22 N2 177.67(13) . . . . ?
C22 N2 C23 O1 -174.81(15) . . . . ?
C24 N2 C23 O1 -2.1(2) . . . . ?
C22 N2 C23 C20 4.5(2) . . . . ?
C24 N2 C23 C20 177.18(14) . . . . ?
C19 C20 C23 O1 -5.7(3) . . . . ?
C21 C20 C23 O1 172.62(15) . . . . ?
C19 C20 C23 N2 175.06(14) . . . . ?
C21 C20 C23 N2 -6.7(2) . . . . ?

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
C2 H2 O1 0.95 2.52 3.399(2) 154.1 1_565

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.065


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_SPA1165
_database_code_depnum_ccdc_archive 'CCDC 1579630'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 N O3'
_chemical_formula_sum            'C29 H21 N O3'
_chemical_formula_weight         431.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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                   17.341(2)
_cell_length_b                   9.321(2)
_cell_length_c                   14.471(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.962(4)
_cell_angle_gamma                90
_cell_volume                     2169.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    43952
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.009
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9571
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.487
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4946
_reflns_number_gt                3302
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.5.1'
_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)+(0.0700P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.059(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4946
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
O1 O 0.82649(7) 0.17768(11) 0.40993(8) 0.0482(3) Uani 1 1 d . . . . .
O2 O 0.94553(7) 0.01044(11) 0.74340(8) 0.0464(3) Uani 1 1 d . . . . .
O3 O 0.51862(8) 0.92881(12) 0.11950(8) 0.0541(3) Uani 1 1 d . . . . .
N1 N 0.68223(7) 0.78223(12) 0.51919(8) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.45402(14) 0.8408(2) 0.05382(14) 0.0715(6) Uani 1 1 d . . . . .
H1A H 0.430466 0.886503 -0.010969 0.107 Uiso 1 1 calc R U . . .
H1B H 0.410988 0.828002 0.080766 0.107 Uiso 1 1 calc R U . . .
H1C H 0.476694 0.748037 0.046998 0.107 Uiso 1 1 calc R U . . .
C2 C 0.55587(9) 0.88608(15) 0.21603(11) 0.0370(3) Uani 1 1 d . . . . .
C3 C 0.54220(9) 0.75569(15) 0.25259(11) 0.0400(4) Uani 1 1 d . . . . .
H3 H 0.504945 0.689312 0.209866 0.048 Uiso 1 1 calc R U . . .
C4 C 0.58357(9) 0.72296(14) 0.35252(11) 0.0385(4) Uani 1 1 d . . . . .
H4 H 0.573078 0.634908 0.377255 0.046 Uiso 1 1 calc R U . . .
C5 C 0.64000(8) 0.81754(14) 0.41646(10) 0.0320(3) Uani 1 1 d . . . . .
C6 C 0.65423(9) 0.94799(15) 0.37923(11) 0.0368(3) Uani 1 1 d . . . . .
H6 H 0.692454 1.013438 0.421613 0.044 Uiso 1 1 calc R U . . .
C7 C 0.61232(10) 0.98169(15) 0.28009(12) 0.0405(4) Uani 1 1 d . . . . .
H7 H 0.622062 1.070438 0.255565 0.049 Uiso 1 1 calc R U . . .
C8 C 0.72237(8) 0.64927(14) 0.54575(10) 0.0317(3) Uani 1 1 d . . . . .
C9 C 0.75376(9) 0.57899(15) 0.48202(11) 0.0377(3) Uani 1 1 d . . . . .
H9 H 0.747756 0.621328 0.420750 0.045 Uiso 1 1 calc R U . . .
C10 C 0.79335(9) 0.44867(15) 0.50765(11) 0.0376(3) Uani 1 1 d . . . . .
H10 H 0.813794 0.403267 0.463442 0.045 Uiso 1 1 calc R U . . .
C11 C 0.80373(8) 0.38242(14) 0.59848(10) 0.0328(3) Uani 1 1 d . . . . .
C12 C 0.77200(9) 0.45433(14) 0.66183(11) 0.0365(3) Uani 1 1 d . . . . .
H12 H 0.778663 0.412944 0.723587 0.044 Uiso 1 1 calc R U . . .
C13 C 0.73145(9) 0.58364(15) 0.63604(11) 0.0363(3) Uani 1 1 d . . . . .
H13 H 0.709726 0.628122 0.679365 0.044 Uiso 1 1 calc R U . . .
C14 C 0.84765(8) 0.24971(14) 0.63357(11) 0.0351(3) Uani 1 1 d . . . . .
H14 H 0.860339 0.234030 0.701856 0.042 Uiso 1 1 calc R U . . .
C15 C 0.87474(8) 0.14247(14) 0.58997(10) 0.0333(3) Uani 1 1 d . . . . .
C16 C 0.86130(9) 0.10726(14) 0.48524(11) 0.0355(3) Uani 1 1 d . . . . .
C17 C 0.89638(9) -0.03973(14) 0.48671(11) 0.0369(3) Uani 1 1 d . . . . .
C18 C 0.89937(10) -0.12211(17) 0.40812(13) 0.0473(4) Uani 1 1 d . . . . .
H18 H 0.876875 -0.088251 0.342192 0.057 Uiso 1 1 calc R U . . .
C19 C 0.93671(10) -0.25616(17) 0.43025(14) 0.0546(5) Uani 1 1 d . . . . .
H19 H 0.939597 -0.314106 0.378478 0.066 Uiso 1 1 calc R U . . .
C20 C 0.96976(11) -0.30577(17) 0.52747(15) 0.0575(5) Uani 1 1 d . . . . .
H20 H 0.994771 -0.396878 0.540392 0.069 Uiso 1 1 calc R U . . .
C21 C 0.96680(10) -0.22436(16) 0.60595(13) 0.0481(4) Uani 1 1 d . . . . .
H21 H 0.988810 -0.258786 0.671753 0.058 Uiso 1 1 calc R U . . .
C22 C 0.93017(9) -0.09012(14) 0.58391(12) 0.0378(4) Uani 1 1 d . . . . .
C23 C 0.92052(9) 0.01973(15) 0.65259(11) 0.0363(3) Uani 1 1 d . . . . .
C24 C 0.68244(9) 0.88420(14) 0.59229(10) 0.0330(3) Uani 1 1 d . . . . .
C25 C 0.61289(10) 0.96741(17) 0.57833(12) 0.0449(4) Uani 1 1 d . . . . .
H25 H 0.564586 0.954566 0.521054 0.054 Uiso 1 1 calc R U . . .
C26 C 0.61415(11) 1.06946(18) 0.64834(13) 0.0518(4) Uani 1 1 d . . . . .
H26 H 0.566486 1.125067 0.638395 0.062 Uiso 1 1 calc R U . . .
C27 C 0.68429(11) 1.09036(16) 0.73220(12) 0.0501(4) Uani 1 1 d . . . . .
H27 H 0.684867 1.159870 0.779514 0.060 Uiso 1 1 calc R U . . .
C28 C 0.75360(11) 1.00847(16) 0.74609(12) 0.0446(4) Uani 1 1 d . . . . .
H28 H 0.801942 1.022769 0.803088 0.054 Uiso 1 1 calc R U . . .
C29 C 0.75312(9) 0.90534(15) 0.67729(11) 0.0381(3) Uani 1 1 d . . . . .
H29 H 0.800786 0.849338 0.688086 0.046 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 C16 1.2210(17) . ?
O2 C23 1.2231(18) . ?
O3 C2 1.3610(18) . ?
O3 C1 1.426(2) . ?
N1 C8 1.4029(17) . ?
N1 C24 1.4211(17) . ?
N1 C5 1.4283(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.381(2) . ?
C2 C7 1.390(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.3834(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.389(2) . ?
C6 C7 1.380(2) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C8 C9 1.397(2) . ?
C8 C13 1.3972(19) . ?
C9 C10 1.3763(19) . ?
C9 H9 0.9400 . ?
C10 C11 1.4016(19) . ?
C10 H10 0.9400 . ?
C11 C12 1.4034(19) . ?
C11 C14 1.4418(18) . ?
C12 C13 1.3749(19) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.356(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.481(2) . ?
C15 C23 1.4907(19) . ?
C16 C17 1.4959(19) . ?
C17 C22 1.388(2) . ?
C17 C18 1.389(2) . ?
C18 C19 1.388(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.385(3) . ?
C19 H19 0.9400 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9400 . ?
C21 C22 1.385(2) . ?
C21 H21 0.9400 . ?
C22 C23 1.479(2) . ?
C24 C25 1.384(2) . ?
C24 C29 1.388(2) . ?
C25 C26 1.384(2) . ?
C25 H25 0.9400 . ?
C26 C27 1.373(2) . ?
C26 H26 0.9400 . ?
C27 C28 1.374(2) . ?
C27 H27 0.9400 . ?
C28 C29 1.382(2) . ?
C28 H28 0.9400 . ?
C29 H29 0.9400 . ?

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 O3 C1 117.94(13) . . ?
C8 N1 C24 121.60(11) . . ?
C8 N1 C5 119.83(11) . . ?
C24 N1 C5 118.57(11) . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C2 C3 124.56(14) . . ?
O3 C2 C7 116.25(13) . . ?
C3 C2 C7 119.18(13) . . ?
C2 C3 C4 119.81(13) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 121.20(13) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.83(13) . . ?
C4 C5 N1 120.56(12) . . ?
C6 C5 N1 120.60(12) . . ?
C7 C6 C5 120.10(13) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C2 120.86(13) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
C9 C8 C13 118.46(12) . . ?
C9 C8 N1 120.61(12) . . ?
C13 C8 N1 120.92(12) . . ?
C10 C9 C8 120.95(13) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 121.18(13) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 117.26(12) . . ?
C10 C11 C14 125.02(13) . . ?
C12 C11 C14 117.65(13) . . ?
C13 C12 C11 121.80(13) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C8 120.33(13) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C15 C14 C11 134.24(14) . . ?
C15 C14 H14 112.9 . . ?
C11 C14 H14 112.9 . . ?
C14 C15 C16 133.61(13) . . ?
C14 C15 C23 118.76(13) . . ?
C16 C15 C23 107.23(12) . . ?
O1 C16 C15 129.06(13) . . ?
O1 C16 C17 124.59(14) . . ?
C15 C16 C17 106.31(12) . . ?
C22 C17 C18 120.78(14) . . ?
C22 C17 C16 109.86(13) . . ?
C18 C17 C16 129.35(14) . . ?
C19 C18 C17 117.75(16) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
C20 C19 C18 120.99(16) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 121.51(15) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 117.47(16) . . ?
C20 C21 H21 121.3 . . ?
C22 C21 H21 121.3 . . ?
C21 C22 C17 121.50(15) . . ?
C21 C22 C23 128.89(15) . . ?
C17 C22 C23 109.61(12) . . ?
O2 C23 C22 126.08(13) . . ?
O2 C23 C15 126.99(13) . . ?
C22 C23 C15 106.93(12) . . ?
C25 C24 C29 118.84(13) . . ?
C25 C24 N1 120.45(13) . . ?
C29 C24 N1 120.68(13) . . ?
C24 C25 C26 120.27(15) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.71(15) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 119.20(15) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
C27 C28 C29 120.79(15) . . ?
C27 C28 H28 119.6 . . ?
C29 C28 H28 119.6 . . ?
C28 C29 C24 120.18(14) . . ?
C28 C29 H29 119.9 . . ?
C24 C29 H29 119.9 . . ?

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
C1 O3 C2 C3 7.6(2) . . . . ?
C1 O3 C2 C7 -173.53(15) . . . . ?
O3 C2 C3 C4 180.00(14) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C3 C4 C5 N1 -179.91(13) . . . . ?
C8 N1 C5 C4 50.20(18) . . . . ?
C24 N1 C5 C4 -129.90(15) . . . . ?
C8 N1 C5 C6 -130.47(14) . . . . ?
C24 N1 C5 C6 49.43(18) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
N1 C5 C6 C7 -179.21(13) . . . . ?
C5 C6 C7 C2 -0.4(2) . . . . ?
O3 C2 C7 C6 -179.23(14) . . . . ?
C3 C2 C7 C6 -0.3(2) . . . . ?
C24 N1 C8 C9 -151.65(14) . . . . ?
C5 N1 C8 C9 28.2(2) . . . . ?
C24 N1 C8 C13 28.8(2) . . . . ?
C5 N1 C8 C13 -151.35(13) . . . . ?
C13 C8 C9 C10 -0.5(2) . . . . ?
N1 C8 C9 C10 179.87(13) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C9 C10 C11 C14 -176.93(14) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C14 C11 C12 C13 178.02(13) . . . . ?
C11 C12 C13 C8 -1.5(2) . . . . ?
C9 C8 C13 C12 1.4(2) . . . . ?
N1 C8 C13 C12 -179.03(13) . . . . ?
C10 C11 C14 C15 -15.0(3) . . . . ?
C12 C11 C14 C15 167.95(15) . . . . ?
C11 C14 C15 C16 -9.3(3) . . . . ?
C11 C14 C15 C23 178.94(14) . . . . ?
C14 C15 C16 O1 7.6(3) . . . . ?
C23 C15 C16 O1 179.99(15) . . . . ?
C14 C15 C16 C17 -170.04(15) . . . . ?
C23 C15 C16 C17 2.36(15) . . . . ?
O1 C16 C17 C22 -178.91(14) . . . . ?
C15 C16 C17 C22 -1.15(16) . . . . ?
O1 C16 C17 C18 2.1(3) . . . . ?
C15 C16 C17 C18 179.86(15) . . . . ?
C22 C17 C18 C19 0.4(2) . . . . ?
C16 C17 C18 C19 179.28(15) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C19 C20 C21 C22 -0.6(3) . . . . ?
C20 C21 C22 C17 1.1(2) . . . . ?
C20 C21 C22 C23 -178.32(15) . . . . ?
C18 C17 C22 C21 -1.0(2) . . . . ?
C16 C17 C22 C21 179.95(13) . . . . ?
C18 C17 C22 C23 178.53(14) . . . . ?
C16 C17 C22 C23 -0.56(16) . . . . ?
C21 C22 C23 O2 1.4(3) . . . . ?
C17 C22 C23 O2 -178.02(14) . . . . ?
C21 C22 C23 C15 -178.51(15) . . . . ?
C17 C22 C23 C15 2.04(16) . . . . ?
C14 C15 C23 O2 -8.9(2) . . . . ?
C16 C15 C23 O2 177.36(14) . . . . ?
C14 C15 C23 C22 171.03(13) . . . . ?
C16 C15 C23 C22 -2.70(15) . . . . ?
C8 N1 C24 C25 -142.90(15) . . . . ?
C5 N1 C24 C25 37.20(19) . . . . ?
C8 N1 C24 C29 39.2(2) . . . . ?
C5 N1 C24 C29 -140.73(14) . . . . ?
C29 C24 C25 C26 -0.2(2) . . . . ?
N1 C24 C25 C26 -178.14(15) . . . . ?
C24 C25 C26 C27 0.4(3) . . . . ?
C25 C26 C27 C28 -0.1(3) . . . . ?
C26 C27 C28 C29 -0.5(3) . . . . ?
C27 C28 C29 C24 0.7(2) . . . . ?
C25 C24 C29 C28 -0.4(2) . . . . ?
N1 C24 C29 C28 177.61(13) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_SPA144
_database_code_depnum_ccdc_archive 'CCDC 1579627'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2017-12-26 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         'C26 H23 N3 O4'
_chemical_formula_sum            'C26 H23 N3 O4'
_chemical_formula_weight         441.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0090 0.0050 '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                   9.7280(19)
_cell_length_b                   9.7480(19)
_cell_length_c                   12.153(2)
_cell_angle_alpha                103.57(3)
_cell_angle_beta                 98.82(3)
_cell_angle_gamma                99.79(3)
_cell_volume                     1081.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    34965
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11249
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.560
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             5693
_reflns_number_gt                4528
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.5.1'
_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)+(0.0943P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.099(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5693
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_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
O1 O 0.58435(9) 0.32619(9) 0.59450(7) 0.02609(19) Uani 1 1 d . . . . .
O2 O 0.90290(12) 0.73958(11) 0.45949(10) 0.0528(3) Uani 1 1 d . . . . .
O3 O 1.29227(9) 0.93628(11) 0.74196(10) 0.0422(3) Uani 1 1 d . . . . .
O4 O 0.99409(10) 0.55120(12) 0.78307(8) 0.0374(2) Uani 1 1 d . . . . .
N1 N 0.37334(10) 0.22082(10) 0.18954(8) 0.0240(2) Uani 1 1 d . . . . .
N2 N 1.10589(10) 0.82301(11) 0.59390(9) 0.0283(2) Uani 1 1 d . . . . .
N3 N 1.13202(10) 0.75493(11) 0.76808(9) 0.0272(2) Uani 1 1 d . . . . .
C1 C 0.34104(11) 0.28231(12) 0.09472(9) 0.0226(2) Uani 1 1 d . . . . .
C2 C 0.28912(15) 0.40807(15) 0.11228(12) 0.0347(3) Uani 1 1 d . . . . .
H2 H 0.2831 0.4580 0.1879 0.042 Uiso 1 1 calc R U . . .
C3 C 0.24622(18) 0.46051(17) 0.01921(14) 0.0442(4) Uani 1 1 d . . . . .
H3 H 0.2100 0.5463 0.0312 0.053 Uiso 1 1 calc R U . . .
C4 C 0.25548(16) 0.38969(17) -0.09039(12) 0.0397(3) Uani 1 1 d . . . . .
H4 H 0.2244 0.4254 -0.1541 0.048 Uiso 1 1 calc R U . . .
C5 C 0.31017(15) 0.26632(16) -0.10765(11) 0.0386(3) Uani 1 1 d . . . . .
H5 H 0.3184 0.2184 -0.1833 0.046 Uiso 1 1 calc R U . . .
C6 C 0.35341(13) 0.21149(14) -0.01508(11) 0.0302(3) Uani 1 1 d . . . . .
H6 H 0.3909 0.1266 -0.0272 0.036 Uiso 1 1 calc R U . . .
C7 C 0.28108(11) 0.08866(12) 0.18671(9) 0.0221(2) Uani 1 1 d . . . . .
C8 C 0.13475(12) 0.07122(13) 0.15341(10) 0.0271(2) Uani 1 1 d . . . . .
H8 H 0.0961 0.1468 0.1324 0.033 Uiso 1 1 calc R U . . .
C9 C 0.04519(13) -0.05687(15) 0.15092(12) 0.0333(3) Uani 1 1 d . . . . .
H9 H -0.0549 -0.0684 0.1286 0.040 Uiso 1 1 calc R U . . .
C10 C 0.10022(14) -0.16790(15) 0.18064(12) 0.0354(3) Uani 1 1 d . . . . .
H10 H 0.0384 -0.2550 0.1796 0.042 Uiso 1 1 calc R U . . .
C11 C 0.24638(14) -0.15097(14) 0.21192(12) 0.0354(3) Uani 1 1 d . . . . .
H11 H 0.2846 -0.2272 0.2322 0.043 Uiso 1 1 calc R U . . .
C12 C 0.33780(13) -0.02379(13) 0.21393(11) 0.0297(3) Uani 1 1 d . . . . .
H12 H 0.4380 -0.0138 0.2337 0.036 Uiso 1 1 calc R U . . .
C13 C 0.47699(11) 0.29752(11) 0.28533(9) 0.0201(2) Uani 1 1 d . . . . .
C14 C 0.47644(11) 0.27033(11) 0.39343(9) 0.0211(2) Uani 1 1 d . . . . .
H14 H 0.4018 0.1996 0.4023 0.025 Uiso 1 1 calc R U . . .
C15 C 0.58350(10) 0.34541(11) 0.48720(9) 0.0193(2) Uani 1 1 d . . . . .
C16 C 0.70026(10) 0.45028(11) 0.47721(9) 0.0186(2) Uani 1 1 d . . . . .
C17 C 0.69436(11) 0.47731(11) 0.36788(10) 0.0219(2) Uani 1 1 d . . . . .
H17 H 0.7681 0.5482 0.3581 0.026 Uiso 1 1 calc R U . . .
C18 C 0.58659(11) 0.40564(12) 0.27501(10) 0.0231(2) Uani 1 1 d . . . . .
H18 H 0.5858 0.4290 0.2033 0.028 Uiso 1 1 calc R U . . .
C19 C 0.46853(12) 0.22452(14) 0.60882(11) 0.0294(3) Uani 1 1 d . . . . .
H19A H 0.3783 0.2492 0.5812 0.044 Uiso 1 1 calc R U . . .
H19B H 0.4776 0.2274 0.6908 0.044 Uiso 1 1 calc R U . . .
H19C H 0.4703 0.1272 0.5643 0.044 Uiso 1 1 calc R U . . .
C20 C 0.81301(11) 0.51102(12) 0.57660(9) 0.0211(2) Uani 1 1 d . . . . .
H20 H 0.8035 0.4618 0.6347 0.025 Uiso 1 1 calc R U . . .
C21 C 0.93175(11) 0.62234(11) 0.60993(10) 0.0216(2) Uani 1 1 d . . . . .
C22 C 0.97371(13) 0.72846(12) 0.54770(11) 0.0288(3) Uani 1 1 d . . . . .
C23 C 1.18359(12) 0.84295(13) 0.70357(11) 0.0279(3) Uani 1 1 d . . . . .
C24 C 1.01862(12) 0.63534(13) 0.72475(10) 0.0250(2) Uani 1 1 d . . . . .
C25 C 1.16272(16) 0.91568(17) 0.52506(15) 0.0452(4) Uani 1 1 d . . . . .
H25A H 1.1468 1.0132 0.5538 0.068 Uiso 1 1 calc R U . . .
H25B H 1.1142 0.8759 0.4439 0.068 Uiso 1 1 calc R U . . .
H25C H 1.2651 0.9199 0.5314 0.068 Uiso 1 1 calc R U . . .
C26 C 1.20889(15) 0.78310(16) 0.88748(12) 0.0387(3) Uani 1 1 d . . . . .
H26A H 1.3060 0.7681 0.8874 0.058 Uiso 1 1 calc R U . . .
H26B H 1.1594 0.7170 0.9253 0.058 Uiso 1 1 calc R U . . .
H26C H 1.2127 0.8831 0.9295 0.058 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 C15 1.3592(13) . ?
O1 C19 1.4294(14) . ?
O2 C22 1.2202(16) . ?
O3 C23 1.2188(15) . ?
O4 C24 1.2207(16) . ?
N1 C13 1.3806(15) . ?
N1 C7 1.4293(14) . ?
N1 C1 1.4364(14) . ?
N2 C23 1.3802(17) . ?
N2 C22 1.3967(15) . ?
N2 C25 1.4657(18) . ?
N3 C23 1.3756(18) . ?
N3 C24 1.3963(16) . ?
N3 C26 1.4664(17) . ?
C1 C6 1.3846(17) . ?
C1 C2 1.3872(17) . ?
C2 C3 1.3834(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3884(16) . ?
C7 C12 1.3912(16) . ?
C8 C9 1.3868(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3850(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3902(17) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.4005(15) . ?
C13 C18 1.4086(15) . ?
C14 C15 1.3799(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.4338(14) . ?
C16 C17 1.4085(15) . ?
C16 C20 1.4317(16) . ?
C17 C18 1.3708(16) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3783(15) . ?
C20 H20 0.9500 . ?
C21 C22 1.4584(17) . ?
C21 C24 1.4819(16) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C15 O1 C19 117.76(9) . . ?
C13 N1 C7 122.14(10) . . ?
C13 N1 C1 120.29(9) . . ?
C7 N1 C1 116.99(9) . . ?
C23 N2 C22 124.67(11) . . ?
C23 N2 C25 116.94(11) . . ?
C22 N2 C25 118.25(11) . . ?
C23 N3 C24 124.25(10) . . ?
C23 N3 C26 117.22(11) . . ?
C24 N3 C26 118.36(12) . . ?
C6 C1 C2 120.17(11) . . ?
C6 C1 N1 120.01(11) . . ?
C2 C1 N1 119.70(11) . . ?
C3 C2 C1 119.77(13) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.58(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.72(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.54(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.19(13) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C8 C7 C12 120.03(11) . . ?
C8 C7 N1 119.79(11) . . ?
C12 C7 N1 120.15(10) . . ?
C9 C8 C7 119.80(12) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.62(11) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.39(12) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 120.76(12) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 119.35(11) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
N1 C13 C14 121.55(10) . . ?
N1 C13 C18 119.71(10) . . ?
C14 C13 C18 118.74(10) . . ?
C15 C14 C13 120.52(10) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
O1 C15 C14 122.44(10) . . ?
O1 C15 C16 115.89(10) . . ?
C14 C15 C16 121.67(10) . . ?
C17 C16 C20 126.91(10) . . ?
C17 C16 C15 115.87(10) . . ?
C20 C16 C15 117.14(10) . . ?
C18 C17 C16 122.74(10) . . ?
C18 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
C17 C18 C13 120.32(10) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C16 136.61(11) . . ?
C21 C20 H20 111.7 . . ?
C16 C20 H20 111.7 . . ?
C20 C21 C22 127.08(10) . . ?
C20 C21 C24 114.00(10) . . ?
C22 C21 C24 118.84(10) . . ?
O2 C22 N2 118.57(12) . . ?
O2 C22 C21 125.05(11) . . ?
N2 C22 C21 116.37(11) . . ?
O3 C23 N3 121.58(12) . . ?
O3 C23 N2 121.14(13) . . ?
N3 C23 N2 117.28(10) . . ?
O4 C24 N3 119.46(11) . . ?
O4 C24 C21 124.06(11) . . ?
N3 C24 C21 116.45(11) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 C1 C6 121.90(12) . . . . ?
C7 N1 C1 C6 -66.64(14) . . . . ?
C13 N1 C1 C2 -62.05(16) . . . . ?
C7 N1 C1 C2 109.41(13) . . . . ?
C6 C1 C2 C3 1.7(2) . . . . ?
N1 C1 C2 C3 -174.36(12) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C2 C1 C6 C5 -1.43(18) . . . . ?
N1 C1 C6 C5 174.60(10) . . . . ?
C4 C5 C6 C1 -0.05(19) . . . . ?
C13 N1 C7 C8 128.80(12) . . . . ?
C1 N1 C7 C8 -42.48(15) . . . . ?
C13 N1 C7 C12 -53.09(16) . . . . ?
C1 N1 C7 C12 135.62(12) . . . . ?
C12 C7 C8 C9 2.04(18) . . . . ?
N1 C7 C8 C9 -179.85(11) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C7 1.5(2) . . . . ?
C8 C7 C12 C11 -2.58(19) . . . . ?
N1 C7 C12 C11 179.32(12) . . . . ?
C7 N1 C13 C14 -15.41(16) . . . . ?
C1 N1 C13 C14 155.59(11) . . . . ?
C7 N1 C13 C18 164.41(10) . . . . ?
C1 N1 C13 C18 -24.59(16) . . . . ?
N1 C13 C14 C15 178.07(10) . . . . ?
C18 C13 C14 C15 -1.75(16) . . . . ?
C19 O1 C15 C14 -0.38(16) . . . . ?
C19 O1 C15 C16 178.89(10) . . . . ?
C13 C14 C15 O1 177.55(10) . . . . ?
C13 C14 C15 C16 -1.68(16) . . . . ?
O1 C15 C16 C17 -175.84(9) . . . . ?
C14 C15 C16 C17 3.44(15) . . . . ?
O1 C15 C16 C20 7.06(14) . . . . ?
C14 C15 C16 C20 -173.67(10) . . . . ?
C20 C16 C17 C18 174.91(10) . . . . ?
C15 C16 C17 C18 -1.87(16) . . . . ?
C16 C17 C18 C13 -1.45(17) . . . . ?
N1 C13 C18 C17 -176.52(10) . . . . ?
C14 C13 C18 C17 3.31(17) . . . . ?
C17 C16 C20 C21 12.8(2) . . . . ?
C15 C16 C20 C21 -170.45(12) . . . . ?
C16 C20 C21 C22 5.6(2) . . . . ?
C16 C20 C21 C24 -177.71(12) . . . . ?
C23 N2 C22 O2 166.21(13) . . . . ?
C25 N2 C22 O2 -9.3(2) . . . . ?
C23 N2 C22 C21 -14.14(18) . . . . ?
C25 N2 C22 C21 170.39(12) . . . . ?
C20 C21 C22 O2 5.4(2) . . . . ?
C24 C21 C22 O2 -171.17(13) . . . . ?
C20 C21 C22 N2 -174.25(11) . . . . ?
C24 C21 C22 N2 9.20(16) . . . . ?
C24 N3 C23 O3 -171.89(11) . . . . ?
C26 N3 C23 O3 3.26(17) . . . . ?
C24 N3 C23 N2 9.17(16) . . . . ?
C26 N3 C23 N2 -175.68(10) . . . . ?
C22 N2 C23 O3 -173.54(12) . . . . ?
C25 N2 C23 O3 1.98(18) . . . . ?
C22 N2 C23 N3 5.40(17) . . . . ?
C25 N2 C23 N3 -179.07(11) . . . . ?
C23 N3 C24 O4 168.99(11) . . . . ?
C26 N3 C24 O4 -6.11(16) . . . . ?
C23 N3 C24 C21 -13.04(16) . . . . ?
C26 N3 C24 C21 171.86(10) . . . . ?
C20 C21 C24 O4 4.16(17) . . . . ?
C22 C21 C24 O4 -178.85(11) . . . . ?
C20 C21 C24 N3 -173.72(9) . . . . ?
C22 C21 C24 N3 3.28(15) . . . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_SPA167
_database_code_depnum_ccdc_archive 'CCDC 1579629'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2017-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H19 N O2'
_chemical_formula_sum            'C28 H19 N O2'
_chemical_formula_weight         401.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 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 0.0059 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0105 0.0059 '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                   6.868(2)
_cell_length_b                   8.175(2)
_cell_length_c                   18.128(4)
_cell_angle_alpha                81.203(10)
_cell_angle_beta                 86.414(7)
_cell_angle_gamma                86.137(10)
_cell_volume                     1002.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    40568
_cell_measurement_theta_min      0.401
_cell_measurement_theta_max      33.749

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.009
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8651
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             4343
_reflns_number_gt                2899
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.5.1'

_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)+(0.1069P)²] 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     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.254(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4343
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1602
_refine_ls_wR_factor_gt          0.1431
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O1 O 0.34609(17) 0.96702(14) 0.44020(6) 0.0430(3) Uani 1 1 d . . . . .
O2 O 0.09367(17) 0.52341(14) 0.61051(7) 0.0446(3) Uani 1 1 d . . . . .
N1 N 0.6393(2) 0.46760(19) 0.18502(8) 0.0456(4) Uani 1 1 d . . . . .
C1 C 0.5498(2) 0.4980(2) 0.25399(9) 0.0386(4) Uani 1 1 d . . . . .
C2 C 0.5353(2) 0.6583(2) 0.27303(9) 0.0397(4) Uani 1 1 d . . . . .
H2 H 0.585694 0.746347 0.239294 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4481(2) 0.6887(2) 0.34070(9) 0.0381(4) Uani 1 1 d . . . . .
H3 H 0.439905 0.797154 0.352460 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3720(2) 0.5605(2) 0.39184(9) 0.0361(4) Uani 1 1 d . . . . .
C5 C 0.3860(2) 0.4008(2) 0.37166(9) 0.0389(4) Uani 1 1 d . . . . .
H5 H 0.334087 0.312986 0.405049 0.047 Uiso 1 1 calc R U . . .
C6 C 0.4733(2) 0.3690(2) 0.30450(10) 0.0398(4) Uani 1 1 d . . . . .
H6 H 0.481483 0.260652 0.292704 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2804(2) 0.5766(2) 0.46447(9) 0.0362(4) Uani 1 1 d . . . . .
H7 H 0.238133 0.474911 0.489691 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2402(2) 0.7012(2) 0.50536(9) 0.0338(4) Uani 1 1 d . . . . .
C9 C 0.2701(2) 0.8815(2) 0.49387(9) 0.0350(4) Uani 1 1 d . . . . .
C10 C 0.1831(2) 0.9447(2) 0.56261(9) 0.0343(4) Uani 1 1 d . . . . .
C11 C 0.1707(3) 1.1047(2) 0.58007(10) 0.0413(4) Uani 1 1 d . . . . .
H11 H 0.225830 1.192035 0.547377 0.050 Uiso 1 1 calc R U . . .
C12 C 0.0750(3) 1.1320(2) 0.64693(10) 0.0448(4) Uani 1 1 d . . . . .
H12 H 0.065182 1.239558 0.659726 0.054 Uiso 1 1 calc R U . . .
C13 C -0.0069(3) 1.0035(2) 0.69548(10) 0.0462(4) Uani 1 1 d . . . . .
H13 H -0.072408 1.025675 0.740296 0.055 Uiso 1 1 calc R U . . .
C14 C 0.0066(2) 0.8438(2) 0.67885(9) 0.0409(4) Uani 1 1 d . . . . .
H14 H -0.048210 0.756529 0.711708 0.049 Uiso 1 1 calc R U . . .
C15 C 0.1038(2) 0.8162(2) 0.61207(9) 0.0349(4) Uani 1 1 d . . . . .
C16 C 0.1394(2) 0.6605(2) 0.58038(9) 0.0358(4) Uani 1 1 d . . . . .
C17 C 0.6028(3) 0.3197(2) 0.15616(9) 0.0407(4) Uani 1 1 d . . . . .
C18 C 0.4153(3) 0.2870(3) 0.14169(12) 0.0534(5) Uani 1 1 d . . . . .
H18 H 0.310316 0.363136 0.149860 0.064 Uiso 1 1 calc R U . . .
C19 C 0.3824(3) 0.1418(3) 0.11516(12) 0.0588(6) Uani 1 1 d . . . . .
H19 H 0.254563 0.119388 0.105774 0.071 Uiso 1 1 calc R U . . .
C20 C 0.5352(3) 0.0299(2) 0.10235(11) 0.0547(5) Uani 1 1 d . . . . .
H20 H 0.511864 -0.068292 0.084197 0.066 Uiso 1 1 calc R U . . .
C21 C 0.7215(3) 0.0626(2) 0.11621(11) 0.0525(5) Uani 1 1 d . . . . .
H21 H 0.826385 -0.012967 0.107140 0.063 Uiso 1 1 calc R U . . .
C22 C 0.7554(3) 0.2065(2) 0.14355(10) 0.0444(4) Uani 1 1 d . . . . .
H22 H 0.883202 0.227494 0.153623 0.053 Uiso 1 1 calc R U . . .
C23 C 0.7991(2) 0.5594(2) 0.15104(10) 0.0401(4) Uani 1 1 d . . . . .
C24 C 0.9460(3) 0.5996(2) 0.19364(10) 0.0434(4) Uani 1 1 d . . . . .
H24 H 0.938786 0.569550 0.245865 0.052 Uiso 1 1 calc R U . . .
C25 C 1.1023(3) 0.6837(2) 0.15867(12) 0.0510(5) Uani 1 1 d . . . . .
H25 H 1.200336 0.712496 0.187434 0.061 Uiso 1 1 calc R U . . .
C26 C 1.1159(3) 0.7261(2) 0.08159(12) 0.0548(5) Uani 1 1 d . . . . .
H26 H 1.223308 0.782235 0.057988 0.066 Uiso 1 1 calc R U . . .
C27 C 0.9703(3) 0.6852(2) 0.03994(11) 0.0547(5) Uani 1 1 d . . . . .
H27 H 0.979147 0.712989 -0.012385 0.066 Uiso 1 1 calc R U . . .
C28 C 0.8121(3) 0.6041(2) 0.07429(10) 0.0484(5) Uani 1 1 d . . . . .
H28 H 0.712282 0.578863 0.045384 0.058 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 C9 1.219(2) . ?
O2 C16 1.221(2) . ?
N1 C1 1.408(2) . ?
N1 C23 1.425(2) . ?
N1 C17 1.432(2) . ?
C1 C6 1.395(2) . ?
C1 C2 1.401(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.404(2) . ?
C4 C7 1.444(2) . ?
C5 C6 1.376(2) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
C7 C8 1.353(2) . ?
C7 H7 0.9400 . ?
C8 C9 1.483(2) . ?
C8 C16 1.488(2) . ?
C9 C10 1.496(2) . ?
C10 C11 1.387(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.384(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.387(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.475(2) . ?
C17 C18 1.382(3) . ?
C17 C22 1.382(2) . ?
C18 C19 1.384(3) . ?
C18 H18 0.9400 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9400 . ?
C20 C21 1.370(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 C28 1.382(2) . ?
C23 C24 1.393(2) . ?
C24 C25 1.381(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.386(3) . ?
C25 H25 0.9400 . ?
C26 C27 1.378(3) . ?
C26 H26 0.9400 . ?
C27 C28 1.377(3) . ?
C27 H27 0.9400 . ?
C28 H28 0.9400 . ?

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
C1 N1 C23 121.26(14) . . ?
C1 N1 C17 119.93(14) . . ?
C23 N1 C17 117.27(13) . . ?
C6 C1 C2 118.85(15) . . ?
C6 C1 N1 120.52(15) . . ?
C2 C1 N1 120.64(16) . . ?
C3 C2 C1 120.85(16) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.82(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 117.65(15) . . ?
C3 C4 C7 125.84(15) . . ?
C5 C4 C7 116.51(15) . . ?
C6 C5 C4 122.01(16) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 119.82(16) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 C7 C4 136.02(16) . . ?
C8 C7 H7 112.0 . . ?
C4 C7 H7 112.0 . . ?
C7 C8 C9 135.23(15) . . ?
C7 C8 C16 117.75(15) . . ?
C9 C8 C16 107.02(14) . . ?
O1 C9 C8 129.14(16) . . ?
O1 C9 C10 124.75(16) . . ?
C8 C9 C10 106.10(14) . . ?
C11 C10 C15 120.27(15) . . ?
C11 C10 C9 129.53(16) . . ?
C15 C10 C9 110.19(15) . . ?
C12 C11 C10 118.18(16) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 121.22(17) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.93(16) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 117.81(16) . . ?
C13 C14 H14 121.1 . . ?
C15 C14 H14 121.1 . . ?
C14 C15 C10 121.57(15) . . ?
C14 C15 C16 129.36(15) . . ?
C10 C15 C16 109.06(14) . . ?
O2 C16 C15 125.91(15) . . ?
O2 C16 C8 126.51(15) . . ?
C15 C16 C8 107.57(14) . . ?
C18 C17 C22 119.25(17) . . ?
C18 C17 N1 120.66(16) . . ?
C22 C17 N1 120.08(16) . . ?
C17 C18 C19 119.82(18) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 120.64(18) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C19 119.64(18) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.09(18) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.55(17) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C28 C23 C24 119.49(16) . . ?
C28 C23 N1 119.40(16) . . ?
C24 C23 N1 121.06(16) . . ?
C25 C24 C23 119.61(17) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.65(18) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C27 C26 C25 119.30(18) . . ?
C27 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C28 C27 C26 120.57(19) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C23 120.37(18) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?

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
C23 N1 C1 C6 -146.77(16) . . . . ?
C17 N1 C1 C6 18.7(3) . . . . ?
C23 N1 C1 C2 33.4(2) . . . . ?
C17 N1 C1 C2 -161.15(16) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
N1 C1 C2 C3 -179.83(15) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C4 C7 179.03(15) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
C7 C4 C5 C6 -178.79(15) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 C5 -179.90(15) . . . . ?
C3 C4 C7 C8 -0.6(3) . . . . ?
C5 C4 C7 C8 178.94(18) . . . . ?
C4 C7 C8 C9 0.8(3) . . . . ?
C4 C7 C8 C16 179.84(17) . . . . ?
C7 C8 C9 O1 -0.6(3) . . . . ?
C16 C8 C9 O1 -179.68(16) . . . . ?
C7 C8 C9 C10 178.34(18) . . . . ?
C16 C8 C9 C10 -0.75(16) . . . . ?
O1 C9 C10 C11 -0.4(3) . . . . ?
C8 C9 C10 C11 -179.36(16) . . . . ?
O1 C9 C10 C15 178.25(15) . . . . ?
C8 C9 C10 C15 -0.73(17) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?
C9 C10 C11 C12 177.43(16) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C10 -0.9(3) . . . . ?
C13 C14 C15 C16 -179.84(16) . . . . ?
C11 C10 C15 C14 1.6(2) . . . . ?
C9 C10 C15 C14 -177.21(14) . . . . ?
C11 C10 C15 C16 -179.28(14) . . . . ?
C9 C10 C15 C16 1.95(18) . . . . ?
C14 C15 C16 O2 -3.2(3) . . . . ?
C10 C15 C16 O2 177.75(16) . . . . ?
C14 C15 C16 C8 176.68(16) . . . . ?
C10 C15 C16 C8 -2.40(18) . . . . ?
C7 C8 C16 O2 2.5(3) . . . . ?
C9 C8 C16 O2 -178.25(15) . . . . ?
C7 C8 C16 C15 -177.39(14) . . . . ?
C9 C8 C16 C15 1.89(17) . . . . ?
C1 N1 C17 C18 59.8(2) . . . . ?
C23 N1 C17 C18 -134.23(19) . . . . ?
C1 N1 C17 C22 -119.24(19) . . . . ?
C23 N1 C17 C22 46.8(2) . . . . ?
C22 C17 C18 C19 0.2(3) . . . . ?
N1 C17 C18 C19 -178.77(18) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C18 C17 C22 C21 0.5(3) . . . . ?
N1 C17 C22 C21 179.50(17) . . . . ?
C20 C21 C22 C17 -0.9(3) . . . . ?
C1 N1 C23 C28 -142.16(17) . . . . ?
C17 N1 C23 C28 52.0(2) . . . . ?
C1 N1 C23 C24 40.2(2) . . . . ?
C17 N1 C23 C24 -125.59(18) . . . . ?
C28 C23 C24 C25 0.2(2) . . . . ?
N1 C23 C24 C25 177.77(15) . . . . ?
C23 C24 C25 C26 -1.1(3) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
C25 C26 C27 C28 0.4(3) . . . . ?
C26 C27 C28 C23 -1.3(3) . . . . ?
C24 C23 C28 C27 1.0(3) . . . . ?
N1 C23 C28 C27 -176.62(17) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_SPA145
_database_code_depnum_ccdc_archive 'CCDC 1579628'
_audit_update_record             
;
2017-10-12 deposited with the CCDC.
2017-12-26 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         'C26 H23 N3 O4'
_chemical_formula_sum            'C26 H23 N3 O4'
_chemical_formula_weight         441.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0020 0.0010 '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 0.0050 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0090 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   38.228(8)
_cell_length_b                   7.2100(14)
_cell_length_c                   16.916(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.72(3)
_cell_angle_gamma                90
_cell_volume                     4361.0(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    63163
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20847
_diffrn_reflns_av_unetI/netI     0.0794
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        22.210
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5946
_reflns_number_gt                3419
_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       
'PAL BL2D-SMDC Program(Shin et. al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND 4(Putz & Brandenburg, 2014)'
_computing_publication_material  'enCifer 1.5.1'
_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)+(0.0709P)²] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0071(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5946
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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 0.51926(4) 1.29595(19) 0.45140(9) 0.0431(4) Uani 1 1 d . . . . .
O2 O 0.34231(3) 0.34685(17) 0.36293(8) 0.0370(3) Uani 1 1 d . . . . .
O3 O 0.25633(3) -0.11167(17) 0.29021(7) 0.0347(3) Uani 1 1 d . . . . .
O4 O 0.23002(3) 0.38728(17) 0.42049(8) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.40930(4) 1.0984(2) 0.58191(8) 0.0276(3) Uani 1 1 d . . . . .
N2 N 0.29965(4) 0.11759(18) 0.32886(8) 0.0225(3) Uani 1 1 d . . . . .
N3 N 0.24425(4) 0.13290(19) 0.36021(8) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.43674(4) 1.1482(2) 0.54598(10) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.42711(5) 1.1750(2) 0.46017(10) 0.0280(4) Uani 1 1 d . . . . .
H2 H 0.4018 1.1601 0.4240 0.034 Uiso 1 1 calc R U . . .
C3 C 0.45401(5) 1.2233(2) 0.42606(11) 0.0294(4) Uani 1 1 d . . . . .
H3 H 0.4472 1.2389 0.3667 0.035 Uiso 1 1 calc R U . . .
C4 C 0.49053(5) 1.2487(2) 0.47838(12) 0.0291(4) Uani 1 1 d . . . . .
C5 C 0.50037(5) 1.2257(3) 0.56501(11) 0.0327(4) Uani 1 1 d . . . . .
H5 H 0.5255 1.2446 0.6013 0.039 Uiso 1 1 calc R U . . .
C6 C 0.47368(5) 1.1753(2) 0.59856(11) 0.0293(4) Uani 1 1 d . . . . .
H6 H 0.4806 1.1590 0.6579 0.035 Uiso 1 1 calc R U . . .
C7 C 0.51037(7) 1.3150(3) 0.36259(15) 0.0544(6) Uani 1 1 d . . . . .
H7A H 0.4997 1.1986 0.3344 0.082 Uiso 1 1 calc R U . . .
H7B H 0.5331 1.3443 0.3511 0.082 Uiso 1 1 calc R U . . .
H7C H 0.4921 1.4153 0.3412 0.082 Uiso 1 1 calc R U . . .
C8 C 0.40546(4) 1.2159(2) 0.64632(9) 0.0237(3) Uani 1 1 d . . . . .
C9 C 0.40187(6) 1.4039(3) 0.63381(12) 0.0383(5) Uani 1 1 d . . . . .
H9 H 0.4028 1.4567 0.5831 0.046 Uiso 1 1 calc R U . . .
C10 C 0.39695(6) 1.5158(3) 0.69503(15) 0.0544(6) Uani 1 1 d . . . . .
H10 H 0.3944 1.6459 0.6861 0.065 Uiso 1 1 calc R U . . .
C11 C 0.39568(6) 1.4415(3) 0.76906(14) 0.0516(6) Uani 1 1 d . . . . .
H11 H 0.3920 1.5193 0.8107 0.062 Uiso 1 1 calc R U . . .
C12 C 0.39984(6) 1.2541(3) 0.78169(11) 0.0440(5) Uani 1 1 d . . . . .
H12 H 0.3992 1.2019 0.8328 0.053 Uiso 1 1 calc R U . . .
C13 C 0.40490(5) 1.1403(3) 0.72116(10) 0.0338(4) Uani 1 1 d . . . . .
H13 H 0.4080 1.0105 0.7307 0.041 Uiso 1 1 calc R U . . .
C14 C 0.38165(4) 0.9665(2) 0.54354(9) 0.0232(3) Uani 1 1 d . . . . .
C15 C 0.38874(5) 0.8171(2) 0.49795(10) 0.0249(4) Uani 1 1 d . . . . .
H15 H 0.4124 0.8078 0.4918 0.030 Uiso 1 1 calc R U . . .
C16 C 0.36200(4) 0.6838(2) 0.46204(10) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.3675 0.5854 0.4309 0.028 Uiso 1 1 calc R U . . .
C17 C 0.32653(4) 0.6905(2) 0.47057(9) 0.0207(3) Uani 1 1 d . . . . .
C18 C 0.31984(4) 0.8425(2) 0.51522(10) 0.0237(3) Uani 1 1 d . . . . .
H18 H 0.2961 0.8524 0.5212 0.028 Uiso 1 1 calc R U . . .
C19 C 0.34618(4) 0.9780(2) 0.55071(10) 0.0250(4) Uani 1 1 d . . . . .
H19 H 0.3404 1.0790 0.5800 0.030 Uiso 1 1 calc R U . . .
C20 C 0.29649(4) 0.5564(2) 0.44209(9) 0.0209(3) Uani 1 1 d . . . . .
H20 H 0.2755 0.5982 0.4548 0.025 Uiso 1 1 calc R U . . .
C21 C 0.28909(4) 0.3885(2) 0.40258(9) 0.0196(3) Uani 1 1 d . . . . .
C22 C 0.31257(4) 0.2886(2) 0.36494(9) 0.0223(3) Uani 1 1 d . . . . .
C23 C 0.26615(4) 0.0382(2) 0.32401(9) 0.0235(3) Uani 1 1 d . . . . .
C24 C 0.25242(4) 0.3086(2) 0.39570(9) 0.0219(3) Uani 1 1 d . . . . .
C25 C 0.32151(5) 0.0192(3) 0.28632(11) 0.0351(4) Uani 1 1 d . . . . .
H25A H 0.3101 0.0381 0.2251 0.053 Uiso 1 1 calc R U . . .
H25B H 0.3219 -0.1135 0.2990 0.053 Uiso 1 1 calc R U . . .
H25C H 0.3471 0.0674 0.3063 0.053 Uiso 1 1 calc R U . . .
C26 C 0.20803(5) 0.0494(3) 0.35141(11) 0.0370(4) Uani 1 1 d . . . . .
H26A H 0.1908 0.0630 0.2929 0.056 Uiso 1 1 calc R U . . .
H26B H 0.1976 0.1119 0.3895 0.056 Uiso 1 1 calc R U . . .
H26C H 0.2115 -0.0826 0.3659 0.056 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 1.3729(19) . ?
O1 C7 1.425(2) . ?
O2 C22 1.2241(19) . ?
O3 C23 1.2177(19) . ?
O4 C24 1.2185(19) . ?
N1 C14 1.399(2) . ?
N1 C8 1.4279(19) . ?
N1 C1 1.4315(19) . ?
N2 C23 1.379(2) . ?
N2 C22 1.387(2) . ?
N2 C25 1.4644(19) . ?
N3 C23 1.380(2) . ?
N3 C24 1.389(2) . ?
N3 C26 1.468(2) . ?
C1 C2 1.379(2) . ?
C1 C6 1.391(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.371(2) . ?
C8 C13 1.385(2) . ?
C9 C10 1.377(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.406(2) . ?
C14 C15 1.406(2) . ?
C15 C16 1.378(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.414(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.405(2) . ?
C17 C20 1.447(2) . ?
C18 C19 1.379(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.363(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.461(2) . ?
C21 C24 1.482(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
C4 O1 C7 117.00(16) . . ?
C14 N1 C8 119.49(13) . . ?
C14 N1 C1 121.34(13) . . ?
C8 N1 C1 117.65(13) . . ?
C23 N2 C22 125.04(13) . . ?
C23 N2 C25 116.69(13) . . ?
C22 N2 C25 118.07(13) . . ?
C23 N3 C24 124.34(13) . . ?
C23 N3 C26 116.76(13) . . ?
C24 N3 C26 118.53(13) . . ?
C2 C1 C6 119.06(15) . . ?
C2 C1 N1 121.29(15) . . ?
C6 C1 N1 119.63(14) . . ?
C1 C2 C3 120.74(16) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.87(16) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O1 C4 C3 124.64(17) . . ?
O1 C4 C5 115.52(16) . . ?
C3 C4 C5 119.84(15) . . ?
C6 C5 C4 120.14(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.34(16) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 119.79(16) . . ?
C9 C8 N1 120.00(15) . . ?
C13 C8 N1 120.21(15) . . ?
C8 C9 C10 119.73(18) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.08(18) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 120.72(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.77(18) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
N1 C14 C19 120.87(14) . . ?
N1 C14 C15 120.97(14) . . ?
C19 C14 C15 118.15(14) . . ?
C16 C15 C14 121.27(14) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 121.34(15) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 116.41(14) . . ?
C18 C17 C20 115.22(14) . . ?
C16 C17 C20 128.32(14) . . ?
C19 C18 C17 122.89(15) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C18 C19 C14 119.92(15) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
C21 C20 C17 139.37(14) . . ?
C21 C20 H20 110.3 . . ?
C17 C20 H20 110.3 . . ?
C20 C21 C22 126.79(14) . . ?
C20 C21 C24 114.22(13) . . ?
C22 C21 C24 118.94(14) . . ?
O2 C22 N2 118.86(14) . . ?
O2 C22 C21 124.25(15) . . ?
N2 C22 C21 116.89(13) . . ?
O3 C23 N2 121.47(15) . . ?
O3 C23 N3 120.85(15) . . ?
N2 C23 N3 117.68(14) . . ?
O4 C24 N3 119.70(14) . . ?
O4 C24 C21 123.52(15) . . ?
N3 C24 C21 116.77(13) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N1 C1 C2 42.3(2) . . . . ?
C8 N1 C1 C2 -123.53(17) . . . . ?
C14 N1 C1 C6 -139.47(17) . . . . ?
C8 N1 C1 C6 54.7(2) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
N1 C1 C2 C3 179.97(16) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C7 O1 C4 C3 -1.7(3) . . . . ?
C7 O1 C4 C5 178.09(16) . . . . ?
C2 C3 C4 O1 179.80(16) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
O1 C4 C5 C6 -178.99(16) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
N1 C1 C6 C5 -179.15(16) . . . . ?
C14 N1 C8 C9 -116.51(19) . . . . ?
C1 N1 C8 C9 49.6(2) . . . . ?
C14 N1 C8 C13 62.7(2) . . . . ?
C1 N1 C8 C13 -131.13(17) . . . . ?
C13 C8 C9 C10 -1.4(3) . . . . ?
N1 C8 C9 C10 177.88(18) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C9 C8 C13 C12 1.6(3) . . . . ?
N1 C8 C13 C12 -177.70(16) . . . . ?
C8 N1 C14 C19 16.5(2) . . . . ?
C1 N1 C14 C19 -149.05(16) . . . . ?
C8 N1 C14 C15 -162.42(15) . . . . ?
C1 N1 C14 C15 32.0(2) . . . . ?
N1 C14 C15 C16 178.15(15) . . . . ?
C19 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C17 -0.9(2) . . . . ?
C15 C16 C17 C18 1.8(2) . . . . ?
C15 C16 C17 C20 -175.40(15) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C20 C17 C18 C19 176.47(14) . . . . ?
C17 C18 C19 C14 -0.5(2) . . . . ?
N1 C14 C19 C18 -177.45(14) . . . . ?
C15 C14 C19 C18 1.5(2) . . . . ?
C18 C17 C20 C21 -175.55(18) . . . . ?
C16 C17 C20 C21 1.7(3) . . . . ?
C17 C20 C21 C22 -7.1(3) . . . . ?
C17 C20 C21 C24 175.50(18) . . . . ?
C23 N2 C22 O2 -177.66(15) . . . . ?
C25 N2 C22 O2 -2.9(2) . . . . ?
C23 N2 C22 C21 1.8(2) . . . . ?
C25 N2 C22 C21 176.50(14) . . . . ?
C20 C21 C22 O2 -1.4(3) . . . . ?
C24 C21 C22 O2 175.82(15) . . . . ?
C20 C21 C22 N2 179.16(14) . . . . ?
C24 C21 C22 N2 -3.6(2) . . . . ?
C22 N2 C23 O3 178.90(14) . . . . ?
C25 N2 C23 O3 4.1(2) . . . . ?
C22 N2 C23 N3 -2.2(2) . . . . ?
C25 N2 C23 N3 -176.99(14) . . . . ?
C24 N3 C23 O3 -176.25(14) . . . . ?
C26 N3 C23 O3 -3.4(2) . . . . ?
C24 N3 C23 N2 4.9(2) . . . . ?
C26 N3 C23 N2 177.67(14) . . . . ?
C23 N3 C24 O4 174.47(15) . . . . ?
C26 N3 C24 O4 1.8(2) . . . . ?
C23 N3 C24 C21 -6.7(2) . . . . ?
C26 N3 C24 C21 -179.38(14) . . . . ?
C20 C21 C24 O4 2.3(2) . . . . ?
C22 C21 C24 O4 -175.32(15) . . . . ?
C20 C21 C24 N3 -176.54(13) . . . . ?
C22 C21 C24 N3 5.9(2) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056

