# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_mo_d8v17800_0m
_database_code_depnum_ccdc_archive 'CCDC 1834779'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 N2 O2'
_chemical_formula_weight         404.45

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.2176(5)
_cell_length_b                   22.5674(12)
_cell_length_c                   10.3343(5)
_cell_angle_alpha                90
_cell_angle_beta                 117.4990(10)
_cell_angle_gamma                90
_cell_volume                     2113.70(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9986
_cell_measurement_theta_min      4.637
_cell_measurement_theta_max      51.624

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6979
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49545
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.863
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4142
_reflns_number_gt                3318
_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-2013 (Sheldrick, 2013)'
_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)+(0.0529P)²+0.5412P] 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
_refine_ls_extinction_coef       0.019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4142
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001

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 0.26049(15) 0.52564(5) 0.82209(17) 0.0722(4) Uani 1 1 d . . . . .
O2 O 0.31792(15) 0.62926(5) 0.88868(16) 0.0654(4) Uani 1 1 d . . . . .
H2 H 0.2801 0.5965 0.8803 0.098 Uiso 1 1 calc R U . . .
N1 N 0.28441(14) 0.42183(6) 0.67849(16) 0.0531(4) Uani 1 1 d . . . . .
N2 N 0.21171(17) 0.54847(8) 0.39947(18) 0.0738(5) Uani 1 1 d . . . . .
C1 C 0.35161(17) 0.36987(7) 0.67161(17) 0.0484(4) Uani 1 1 d . . . . .
C2 C 0.2897(2) 0.31468(8) 0.6143(2) 0.0637(5) Uani 1 1 d . . . . .
H2A H 0.1884 0.3085 0.5725 0.076 Uiso 1 1 calc R U . . .
C3 C 0.3840(2) 0.27014(8) 0.6221(2) 0.0690(5) Uani 1 1 d . . . . .
H3 H 0.3456 0.2330 0.5851 0.083 Uiso 1 1 calc R U . . .
C4 C 0.5359(2) 0.27902(8) 0.6838(2) 0.0692(5) Uani 1 1 d . . . . .
H4 H 0.5968 0.2478 0.6869 0.083 Uiso 1 1 calc R U . . .
C5 C 0.5967(2) 0.33283(7) 0.7399(2) 0.0579(4) Uani 1 1 d . . . . .
H5 H 0.6983 0.3383 0.7813 0.069 Uiso 1 1 calc R U . . .
C6 C 0.50457(17) 0.37972(6) 0.73448(16) 0.0451(4) Uani 1 1 d . . . . .
C7 C 0.52777(17) 0.44003(7) 0.77730(16) 0.0459(4) Uani 1 1 d . . . . .
H7 H 0.6183 0.4594 0.8215 0.055 Uiso 1 1 calc R U . . .
C8 C 0.39323(16) 0.46466(6) 0.74205(17) 0.0455(4) Uani 1 1 d . . . . .
C9 C 0.36015(18) 0.52350(7) 0.78034(18) 0.0487(4) Uani 1 1 d . . . . .
C10 C 0.43938(16) 0.57559(6) 0.77982(16) 0.0423(3) Uani 1 1 d . . . . .
C11 C 0.54096(16) 0.57576(6) 0.71283(16) 0.0398(3) Uani 1 1 d . . . . .
C12 C 0.48714(16) 0.56519(6) 0.56937(16) 0.0441(3) Uani 1 1 d . . . . .
H12 H 0.5523 0.5637 0.5297 0.053 Uiso 1 1 calc R U . . .
C13 C 0.33400(18) 0.55615(7) 0.47580(17) 0.0508(4) Uani 1 1 d . . . . .
C14 C 0.70144(16) 0.58564(6) 0.80390(16) 0.0445(4) Uani 1 1 d . . . . .
C15 C 0.78795(19) 0.60791(8) 0.7432(2) 0.0616(5) Uani 1 1 d . . . . .
H15 H 0.7432 0.6200 0.6462 0.074 Uiso 1 1 calc R U . . .
C16 C 0.9385(2) 0.61228(10) 0.8245(3) 0.0794(6) Uani 1 1 d . . . . .
H16 H 0.9949 0.6272 0.7825 0.095 Uiso 1 1 calc R U . . .
C17 C 1.0055(2) 0.59461(10) 0.9674(3) 0.0841(7) Uani 1 1 d . . . . .
H17 H 1.1076 0.5967 1.0217 0.101 Uiso 1 1 calc R U . . .
C18 C 0.9228(2) 0.57397(10) 1.0302(2) 0.0803(6) Uani 1 1 d . . . . .
H18 H 0.9687 0.5624 1.1275 0.096 Uiso 1 1 calc R U . . .
C19 C 0.77032(19) 0.57018(8) 0.94958(18) 0.0593(4) Uani 1 1 d . . . . .
H19 H 0.7144 0.5572 0.9940 0.071 Uiso 1 1 calc R U . . .
C20 C 0.41217(17) 0.62762(7) 0.83682(17) 0.0466(4) Uani 1 1 d . . . . .
C21 C 0.48496(16) 0.68519(7) 0.84478(17) 0.0474(4) Uani 1 1 d . . . . .
C22 C 0.4903(2) 0.71002(7) 0.7249(2) 0.0579(4) Uani 1 1 d . . . . .
H22 H 0.4543 0.6891 0.6376 0.069 Uiso 1 1 calc R U . . .
C23 C 0.5493(2) 0.76583(8) 0.7353(3) 0.0764(6) Uani 1 1 d . . . . .
H23 H 0.5503 0.7830 0.6540 0.092 Uiso 1 1 calc R U . . .
C24 C 0.6062(2) 0.79619(9) 0.8645(3) 0.0840(7) Uani 1 1 d . . . . .
H24 H 0.6472 0.8336 0.8711 0.101 Uiso 1 1 calc R U . . .
C25 C 0.6029(2) 0.77159(9) 0.9842(3) 0.0779(6) Uani 1 1 d . . . . .
H25 H 0.6427 0.7921 1.0721 0.094 Uiso 1 1 calc R U . . .
C26 C 0.54073(19) 0.71662(8) 0.9747(2) 0.0613(5) Uani 1 1 d . . . . .
H26 H 0.5362 0.7006 1.0554 0.074 Uiso 1 1 calc R U . . .
C27 C 0.1254(2) 0.43056(9) 0.6052(3) 0.0802(6) Uani 1 1 d . . . . .
H27A H 0.0888 0.4263 0.5018 0.120 Uiso 1 1 calc R U . . .
H27B H 0.1028 0.4696 0.6262 0.120 Uiso 1 1 calc R U . . .
H27C H 0.0796 0.4016 0.6392 0.120 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 1.2772(19) . ?
O2 C20 1.3011(18) . ?
O2 H2 0.8200 . ?
N1 C1 1.377(2) . ?
N1 C8 1.3884(19) . ?
N1 C27 1.455(2) . ?
N2 C13 1.142(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.406(2) . ?
C2 C3 1.369(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.417(2) . ?
C7 C8 1.367(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.469(2) . ?
C9 C10 1.429(2) . ?
C10 C20 1.398(2) . ?
C10 C11 1.490(2) . ?
C11 C12 1.343(2) . ?
C11 C14 1.483(2) . ?
C12 C13 1.424(2) . ?
C12 H12 0.9300 . ?
C14 C19 1.380(2) . ?
C14 C15 1.393(2) . ?
C15 C16 1.374(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.364(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.480(2) . ?
C21 C22 1.384(2) . ?
C21 C26 1.387(2) . ?
C22 C23 1.379(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

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
C20 O2 H2 109.5 . . ?
C1 N1 C8 107.92(13) . . ?
C1 N1 C27 123.52(14) . . ?
C8 N1 C27 127.59(14) . . ?
N1 C1 C2 129.88(15) . . ?
N1 C1 C6 108.43(13) . . ?
C2 C1 C6 121.69(15) . . ?
C3 C2 C1 117.43(17) . . ?
C3 C2 H2A 121.3 . . ?
C1 C2 H2A 121.3 . . ?
C2 C3 C4 121.76(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.97(17) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.29(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C1 118.87(14) . . ?
C5 C6 C7 134.50(15) . . ?
C1 C6 C7 106.62(13) . . ?
C8 C7 C6 107.74(13) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
C7 C8 N1 109.27(13) . . ?
C7 C8 C9 128.60(14) . . ?
N1 C8 C9 121.55(13) . . ?
O1 C9 C10 120.78(14) . . ?
O1 C9 C8 116.33(13) . . ?
C10 C9 C8 122.79(13) . . ?
C20 C10 C9 117.79(13) . . ?
C20 C10 C11 120.69(13) . . ?
C9 C10 C11 121.41(13) . . ?
C12 C11 C14 119.76(13) . . ?
C12 C11 C10 119.63(13) . . ?
C14 C11 C10 120.58(13) . . ?
C11 C12 C13 122.44(14) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
N2 C13 C12 179.0(2) . . ?
C19 C14 C15 118.20(15) . . ?
C19 C14 C11 120.78(14) . . ?
C15 C14 C11 120.94(14) . . ?
C16 C15 C14 120.96(19) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 120.10(18) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.29(19) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
O2 C20 C10 121.77(14) . . ?
O2 C20 C21 113.62(13) . . ?
C10 C20 C21 124.61(13) . . ?
C22 C21 C26 119.44(16) . . ?
C22 C21 C20 122.15(15) . . ?
C26 C21 C20 118.28(15) . . ?
C23 C22 C21 119.75(18) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C24 C23 C22 120.5(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.09(18) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C21 119.96(19) . . ?
C25 C26 H26 120.0 . . ?
C21 C26 H26 120.0 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C8 N1 C1 C2 -178.40(17) . . . . ?
C27 N1 C1 C2 -8.9(3) . . . . ?
C8 N1 C1 C6 1.34(18) . . . . ?
C27 N1 C1 C6 170.82(17) . . . . ?
N1 C1 C2 C3 179.95(17) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -178.19(18) . . . . ?
N1 C1 C6 C5 -179.96(14) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
N1 C1 C6 C7 -1.16(17) . . . . ?
C2 C1 C6 C7 178.62(15) . . . . ?
C5 C6 C7 C8 179.06(17) . . . . ?
C1 C6 C7 C8 0.53(17) . . . . ?
C6 C7 C8 N1 0.29(17) . . . . ?
C6 C7 C8 C9 171.57(14) . . . . ?
C1 N1 C8 C7 -1.02(18) . . . . ?
C27 N1 C8 C7 -169.94(18) . . . . ?
C1 N1 C8 C9 -173.03(14) . . . . ?
C27 N1 C8 C9 18.1(3) . . . . ?
C7 C8 C9 O1 -136.62(17) . . . . ?
N1 C8 C9 O1 33.7(2) . . . . ?
C7 C8 C9 C10 39.9(2) . . . . ?
N1 C8 C9 C10 -149.79(15) . . . . ?
O1 C9 C10 C20 4.8(2) . . . . ?
C8 C9 C10 C20 -171.54(14) . . . . ?
O1 C9 C10 C11 -171.55(15) . . . . ?
C8 C9 C10 C11 12.1(2) . . . . ?
C20 C10 C11 C12 -113.85(16) . . . . ?
C9 C10 C11 C12 62.41(19) . . . . ?
C20 C10 C11 C14 68.05(18) . . . . ?
C9 C10 C11 C14 -115.70(16) . . . . ?
C14 C11 C12 C13 -179.13(13) . . . . ?
C10 C11 C12 C13 2.7(2) . . . . ?
C12 C11 C14 C19 -150.26(16) . . . . ?
C10 C11 C14 C19 27.8(2) . . . . ?
C12 C11 C14 C15 26.4(2) . . . . ?
C10 C11 C14 C15 -155.48(15) . . . . ?
C19 C14 C15 C16 2.4(3) . . . . ?
C11 C14 C15 C16 -174.32(16) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C15 C14 C19 C18 -3.4(3) . . . . ?
C11 C14 C19 C18 173.41(16) . . . . ?
C17 C18 C19 C14 1.9(3) . . . . ?
C9 C10 C20 O2 -0.2(2) . . . . ?
C11 C10 C20 O2 176.23(14) . . . . ?
C9 C10 C20 C21 179.83(14) . . . . ?
C11 C10 C20 C21 -3.8(2) . . . . ?
O2 C20 C21 C22 -128.88(17) . . . . ?
C10 C20 C21 C22 51.1(2) . . . . ?
O2 C20 C21 C26 46.9(2) . . . . ?
C10 C20 C21 C26 -133.13(17) . . . . ?
C26 C21 C22 C23 -0.7(3) . . . . ?
C20 C21 C22 C23 174.94(16) . . . . ?
C21 C22 C23 C24 1.8(3) . . . . ?
C22 C23 C24 C25 -1.0(3) . . . . ?
C23 C24 C25 C26 -0.8(3) . . . . ?
C24 C25 C26 C21 1.8(3) . . . . ?
C22 C21 C26 C25 -1.0(3) . . . . ?
C20 C21 C26 C25 -176.90(16) . . . . ?

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
C27 H27B O1 0.96 2.30 2.946(3) 124.1 .
O2 H2 O1 0.82 1.69 2.4318(17) 149.8 .

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v17495
_database_code_depnum_ccdc_archive 'CCDC 1834807'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 N2 O2'
_chemical_formula_weight         402.43

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   6.9632(9)
_cell_length_b                   20.434(3)
_cell_length_c                   28.769(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4093.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      4.890
_cell_measurement_theta_max      52.653

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5620
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            82706
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.832
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3805
_reflns_number_gt                2902
_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-2013 (Sheldrick, 2013)'
_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)+(0.0625P)²+0.8442P] 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
_refine_ls_extinction_coef       0.0074(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3805
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.54827(19) 0.14348(6) 0.71483(5) 0.0508(4) Uani 1 1 d . . . . .
N2 N 0.5960(3) 0.13467(8) 0.58134(6) 0.0805(5) Uani 1 1 d . . . . .
O1 O 0.6840(2) 0.35677(6) 0.75256(4) 0.0671(4) Uani 1 1 d . . . . .
H1 H 0.7173 0.3921 0.7417 0.101 Uiso 1 1 calc R U . . .
O2 O 0.7393(3) 0.44169(7) 0.68678(6) 0.1172(8) Uani 1 1 d . . . . .
C1 C 0.5928(2) 0.21745(8) 0.77330(6) 0.0491(4) Uani 1 1 d . . . . .
C2 C 0.6046(2) 0.23791(10) 0.81940(6) 0.0613(5) Uani 1 1 d . . . . .
H2 H 0.6304 0.2814 0.8267 0.074 Uiso 1 1 calc R U . . .
C3 C 0.5770(3) 0.19217(12) 0.85390(7) 0.0756(6) Uani 1 1 d . . . . .
H3 H 0.5837 0.2049 0.8849 0.091 Uiso 1 1 calc R U . . .
C4 C 0.5395(3) 0.12752(13) 0.84311(8) 0.0808(7) Uani 1 1 d . . . . .
H4 H 0.5219 0.0977 0.8672 0.097 Uiso 1 1 calc R U . . .
C5 C 0.5273(3) 0.10564(10) 0.79775(8) 0.0690(6) Uani 1 1 d . . . . .
H5 H 0.5021 0.0620 0.7909 0.083 Uiso 1 1 calc R U . . .
C6 C 0.5544(2) 0.15181(8) 0.76280(6) 0.0523(4) Uani 1 1 d . . . . .
C7 C 0.5800(2) 0.20315(7) 0.69429(6) 0.0434(4) Uani 1 1 d . . . . .
C8 C 0.6082(2) 0.25017(7) 0.72931(5) 0.0443(4) Uani 1 1 d . . . . .
C9 C 0.6469(2) 0.31456(8) 0.71765(6) 0.0478(4) Uani 1 1 d . . . . .
C10 C 0.6396(2) 0.33434(7) 0.67074(6) 0.0485(4) Uani 1 1 d . . . . .
C11 C 0.6167(2) 0.28673(7) 0.63546(6) 0.0464(4) Uani 1 1 d . . . . .
C12 C 0.5907(2) 0.22068(7) 0.64687(5) 0.0446(4) Uani 1 1 d . . . . .
C13 C 0.5915(3) 0.17273(8) 0.61029(6) 0.0548(4) Uani 1 1 d . . . . .
C14 C 0.5201(3) 0.08042(8) 0.69207(8) 0.0684(5) Uani 1 1 d . . . . .
H14A H 0.4412 0.0861 0.6650 0.103 Uiso 1 1 calc R U . . .
H14B H 0.4584 0.0508 0.7132 0.103 Uiso 1 1 calc R U . . .
H14C H 0.6424 0.0628 0.6830 0.103 Uiso 1 1 calc R U . . .
C15 C 0.6473(3) 0.40500(8) 0.66112(7) 0.0643(5) Uani 1 1 d . . . . .
C16 C 0.5270(3) 0.43505(7) 0.62439(6) 0.0551(4) Uani 1 1 d . . . . .
C17 C 0.6031(3) 0.47969(8) 0.59336(6) 0.0626(5) Uani 1 1 d . . . . .
H17 H 0.7337 0.4892 0.5941 0.075 Uiso 1 1 calc R U . . .
C18 C 0.4865(4) 0.51004(9) 0.56137(7) 0.0782(6) Uani 1 1 d . . . . .
H18 H 0.5394 0.5389 0.5399 0.094 Uiso 1 1 calc R U . . .
C19 C 0.2947(5) 0.49813(11) 0.56096(9) 0.0952(8) Uani 1 1 d . . . . .
H19 H 0.2167 0.5190 0.5393 0.114 Uiso 1 1 calc R U . . .
C20 C 0.2158(4) 0.45551(12) 0.59230(11) 0.1010(8) Uani 1 1 d . . . . .
H20 H 0.0839 0.4484 0.5924 0.121 Uiso 1 1 calc R U . . .
C21 C 0.3322(3) 0.42299(10) 0.62385(9) 0.0805(6) Uani 1 1 d . . . . .
H21 H 0.2791 0.3931 0.6446 0.097 Uiso 1 1 calc R U . . .
C22 C 0.6414(3) 0.30491(8) 0.58563(6) 0.0510(4) Uani 1 1 d . . . . .
C23 C 0.8172(3) 0.32741(8) 0.57025(6) 0.0593(5) Uani 1 1 d . . . . .
H23 H 0.9183 0.3315 0.5912 0.071 Uiso 1 1 calc R U . . .
C24 C 0.8450(4) 0.34404(10) 0.52405(7) 0.0725(6) Uani 1 1 d . . . . .
H24 H 0.9643 0.3589 0.5140 0.087 Uiso 1 1 calc R U . . .
C25 C 0.6961(4) 0.33856(10) 0.49328(7) 0.0788(7) Uani 1 1 d . . . . .
H25 H 0.7142 0.3500 0.4623 0.095 Uiso 1 1 calc R U . . .
C26 C 0.5203(4) 0.31631(10) 0.50782(7) 0.0806(6) Uani 1 1 d . . . . .
H26 H 0.4194 0.3129 0.4867 0.097 Uiso 1 1 calc R U . . .
C27 C 0.4927(3) 0.29887(9) 0.55377(7) 0.0676(5) Uani 1 1 d . . . . .
H27 H 0.3740 0.2830 0.5634 0.081 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
N1 C7 1.3728(19) . ?
N1 C6 1.391(2) . ?
N1 C14 1.459(2) . ?
N2 C13 1.140(2) . ?
O1 C9 1.3486(19) . ?
O1 H1 0.8200 . ?
O2 C15 1.232(2) . ?
C1 C2 1.393(3) . ?
C1 C6 1.400(2) . ?
C1 C8 1.435(2) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(2) . ?
C5 H5 0.9300 . ?
C7 C8 1.406(2) . ?
C7 C12 1.412(2) . ?
C8 C9 1.384(2) . ?
C9 C10 1.410(2) . ?
C10 C11 1.415(2) . ?
C10 C15 1.471(2) . ?
C11 C12 1.401(2) . ?
C11 C22 1.491(2) . ?
C12 C13 1.438(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.482(2) . ?
C16 C21 1.378(3) . ?
C16 C17 1.382(2) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.358(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C22 C27 1.388(3) . ?
C23 C24 1.385(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.371(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.382(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

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
C7 N1 C6 108.26(13) . . ?
C7 N1 C14 127.81(16) . . ?
C6 N1 C14 123.89(14) . . ?
C9 O1 H1 109.5 . . ?
C2 C1 C6 120.27(16) . . ?
C2 C1 C8 134.04(17) . . ?
C6 C1 C8 105.68(15) . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 122.19(19) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 117.0(2) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
N1 C6 C5 129.02(18) . . ?
N1 C6 C1 109.70(13) . . ?
C5 C6 C1 121.28(18) . . ?
N1 C7 C8 108.73(14) . . ?
N1 C7 C12 130.50(15) . . ?
C8 C7 C12 120.76(13) . . ?
C9 C8 C7 120.21(14) . . ?
C9 C8 C1 132.14(15) . . ?
C7 C8 C1 107.64(14) . . ?
O1 C9 C8 117.69(14) . . ?
O1 C9 C10 122.44(14) . . ?
C8 C9 C10 119.82(14) . . ?
C9 C10 C11 119.58(14) . . ?
C9 C10 C15 117.40(15) . . ?
C11 C10 C15 122.96(15) . . ?
C12 C11 C10 120.60(15) . . ?
C12 C11 C22 118.70(14) . . ?
C10 C11 C22 120.37(14) . . ?
C11 C12 C7 118.52(14) . . ?
C11 C12 C13 118.99(15) . . ?
C7 C12 C13 122.29(14) . . ?
N2 C13 C12 178.7(2) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C10 120.24(16) . . ?
O2 C15 C16 117.98(15) . . ?
C10 C15 C16 121.34(15) . . ?
C21 C16 C17 119.21(18) . . ?
C21 C16 C15 119.36(18) . . ?
C17 C16 C15 121.15(18) . . ?
C18 C17 C16 120.2(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 119.8(2) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C23 C22 C27 118.63(17) . . ?
C23 C22 C11 119.54(15) . . ?
C27 C22 C11 121.82(16) . . ?
C22 C23 C24 120.86(19) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.6(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.44(19) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C27 120.1(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C22 120.4(2) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 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
C6 C1 C2 C3 -0.2(2) . . . . ?
C8 C1 C2 C3 178.30(17) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C7 N1 C6 C5 178.84(16) . . . . ?
C14 N1 C6 C5 -3.4(3) . . . . ?
C7 N1 C6 C1 -0.69(17) . . . . ?
C14 N1 C6 C1 177.07(15) . . . . ?
C4 C5 C6 N1 -179.34(17) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C2 C1 C6 N1 179.56(14) . . . . ?
C8 C1 C6 N1 0.67(17) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C8 C1 C6 C5 -178.90(14) . . . . ?
C6 N1 C7 C8 0.41(16) . . . . ?
C14 N1 C7 C8 -177.23(15) . . . . ?
C6 N1 C7 C12 179.00(15) . . . . ?
C14 N1 C7 C12 1.4(3) . . . . ?
N1 C7 C8 C9 178.73(14) . . . . ?
C12 C7 C8 C9 0.0(2) . . . . ?
N1 C7 C8 C1 0.01(16) . . . . ?
C12 C7 C8 C1 -178.75(13) . . . . ?
C2 C1 C8 C9 2.4(3) . . . . ?
C6 C1 C8 C9 -178.93(16) . . . . ?
C2 C1 C8 C7 -179.08(16) . . . . ?
C6 C1 C8 C7 -0.41(16) . . . . ?
C7 C8 C9 O1 -176.13(14) . . . . ?
C1 C8 C9 O1 2.2(3) . . . . ?
C7 C8 C9 C10 6.2(2) . . . . ?
C1 C8 C9 C10 -175.42(16) . . . . ?
O1 C9 C10 C11 174.48(15) . . . . ?
C8 C9 C10 C11 -8.0(2) . . . . ?
O1 C9 C10 C15 -8.3(3) . . . . ?
C8 C9 C10 C15 169.23(16) . . . . ?
C9 C10 C11 C12 3.6(2) . . . . ?
C15 C10 C11 C12 -173.46(16) . . . . ?
C9 C10 C11 C22 -169.71(15) . . . . ?
C15 C10 C11 C22 13.2(3) . . . . ?
C10 C11 C12 C7 2.5(2) . . . . ?
C22 C11 C12 C7 175.91(14) . . . . ?
C10 C11 C12 C13 -172.47(15) . . . . ?
C22 C11 C12 C13 0.9(2) . . . . ?
N1 C7 C12 C11 177.22(15) . . . . ?
C8 C7 C12 C11 -4.3(2) . . . . ?
N1 C7 C12 C13 -8.0(3) . . . . ?
C8 C7 C12 C13 170.46(15) . . . . ?
C9 C10 C15 O2 32.1(3) . . . . ?
C11 C10 C15 O2 -150.8(2) . . . . ?
C9 C10 C15 C16 -140.21(18) . . . . ?
C11 C10 C15 C16 36.9(3) . . . . ?
O2 C15 C16 C21 -121.1(2) . . . . ?
C10 C15 C16 C21 51.4(3) . . . . ?
O2 C15 C16 C17 52.8(3) . . . . ?
C10 C15 C16 C17 -134.73(19) . . . . ?
C21 C16 C17 C18 -2.1(3) . . . . ?
C15 C16 C17 C18 -176.00(17) . . . . ?
C16 C17 C18 C19 2.2(3) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C21 -1.7(4) . . . . ?
C17 C16 C21 C20 0.1(3) . . . . ?
C15 C16 C21 C20 174.1(2) . . . . ?
C19 C20 C21 C16 1.8(4) . . . . ?
C12 C11 C22 C23 -111.05(18) . . . . ?
C10 C11 C22 C23 62.4(2) . . . . ?
C12 C11 C22 C27 67.9(2) . . . . ?
C10 C11 C22 C27 -118.70(18) . . . . ?
C27 C22 C23 C24 0.4(3) . . . . ?
C11 C22 C23 C24 179.33(16) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C24 C25 C26 -0.5(3) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C22 1.2(3) . . . . ?
C23 C22 C27 C26 -1.2(3) . . . . ?
C11 C22 C27 C26 179.86(17) . . . . ?

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
C14 H14C O2 0.96 2.61 3.296(2) 128.5 8_755
O1 H1 O2 0.82 1.88 2.596(2) 144.7 .
O1 H1 O2 0.82 1.88 2.596(2) 144.7 .
C14 H14C O2 0.96 2.61 3.296(2) 128.5 8_755

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v18043
_database_code_depnum_ccdc_archive 'CCDC 1834808'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2019-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 N2 O2'
_chemical_formula_weight         402.43

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           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                   16.4009(8)
_cell_length_b                   7.8236(4)
_cell_length_c                   31.4855(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.498(3)
_cell_angle_gamma                90
_cell_volume                     3944.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9718
_cell_measurement_theta_min      5.088
_cell_measurement_theta_max      54.991

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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            73827
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.602
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3876
_reflns_number_gt                3492
_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-2013 (Sheldrick, 2013)'
_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)+(0.0553P)²+4.9709P] 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
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3876
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1154
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.017
_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
N1 N 0.63709(8) 0.60976(18) 0.48378(4) 0.0294(3) Uani 1 1 d . . . . .
N2 N 0.92470(9) 0.3303(2) 0.59289(5) 0.0416(4) Uani 1 1 d . . . . .
O1 O 0.54019(7) 0.68432(16) 0.54954(4) 0.0321(3) Uani 1 1 d . . . . .
H1 H 0.5245 0.7167 0.5719 0.048 Uiso 1 1 calc R U . . .
O2 O 0.59420(7) 0.75030(14) 0.64862(4) 0.0309(3) Uani 1 1 d . . . . .
C1 C 0.70195(10) 0.5580(2) 0.46506(5) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.70819(11) 0.5712(2) 0.42161(5) 0.0345(4) Uani 1 1 d . . . . .
H2 H 0.6637 0.6160 0.4000 0.041 Uiso 1 1 calc R U . . .
C3 C 0.78153(12) 0.5164(2) 0.41134(6) 0.0375(4) Uani 1 1 d . . . . .
H3 H 0.7882 0.5266 0.3822 0.045 Uiso 1 1 calc R U . . .
C4 C 0.84635(12) 0.4461(2) 0.44284(6) 0.0371(4) Uani 1 1 d . . . . .
H4 H 0.8958 0.4089 0.4346 0.044 Uiso 1 1 calc R U . . .
C5 C 0.83988(11) 0.4299(2) 0.48546(6) 0.0328(4) Uani 1 1 d . . . . .
H5 H 0.8837 0.3799 0.5065 0.039 Uiso 1 1 calc R U . . .
C6 C 0.76676(10) 0.4889(2) 0.49720(5) 0.0279(3) Uani 1 1 d . . . . .
C7 C 0.73946(9) 0.50258(19) 0.53753(5) 0.0252(3) Uani 1 1 d . . . . .
C8 C 0.65993(9) 0.5785(2) 0.52788(5) 0.0253(3) Uani 1 1 d . . . . .
C9 C 0.61753(9) 0.61432(19) 0.56116(5) 0.0250(3) Uani 1 1 d . . . . .
C10 C 0.65561(9) 0.57166(19) 0.60372(5) 0.0235(3) Uani 1 1 d . . . . .
C11 C 0.73627(9) 0.49739(19) 0.61455(5) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.77727(9) 0.4623(2) 0.58107(5) 0.0249(3) Uani 1 1 d . . . . .
C13 C 0.85941(10) 0.3891(2) 0.58930(5) 0.0285(4) Uani 1 1 d . . . . .
C14 C 0.56198(11) 0.6949(2) 0.45980(6) 0.0371(4) Uani 1 1 d . . . . .
H14A H 0.5156 0.6724 0.4741 0.056 Uiso 1 1 calc R U . . .
H14B H 0.5480 0.6513 0.4299 0.056 Uiso 1 1 calc R U . . .
H14C H 0.5719 0.8183 0.4593 0.056 Uiso 1 1 calc R U . . .
C15 C 0.60573(9) 0.6043(2) 0.63796(5) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.56538(9) 0.4564(2) 0.65476(5) 0.0249(3) Uani 1 1 d . . . . .
C17 C 0.58130(10) 0.2893(2) 0.64403(5) 0.0283(3) Uani 1 1 d . . . . .
H17 H 0.6212 0.2678 0.6269 0.034 Uiso 1 1 calc R U . . .
C18 C 0.53969(10) 0.1540(2) 0.65807(6) 0.0335(4) Uani 1 1 d . . . . .
H18 H 0.5509 0.0401 0.6506 0.040 Uiso 1 1 calc R U . . .
C19 C 0.48153(11) 0.1856(2) 0.68312(6) 0.0406(4) Uani 1 1 d . . . . .
H19 H 0.4529 0.0932 0.6929 0.049 Uiso 1 1 calc R U . . .
C20 C 0.46521(12) 0.3515(3) 0.69382(7) 0.0457(5) Uani 1 1 d . . . . .
H20 H 0.4250 0.3725 0.7109 0.055 Uiso 1 1 calc R U . . .
C21 C 0.50662(11) 0.4872(2) 0.68000(6) 0.0365(4) Uani 1 1 d . . . . .
H21 H 0.4952 0.6009 0.6876 0.044 Uiso 1 1 calc R U . . .
C22 C 0.77569(9) 0.4637(2) 0.66099(5) 0.0254(3) Uani 1 1 d . . . . .
C23 C 0.81106(10) 0.3043(2) 0.67440(5) 0.0302(4) Uani 1 1 d . . . . .
H23 H 0.8105 0.2159 0.6536 0.036 Uiso 1 1 calc R U . . .
C24 C 0.84676(11) 0.2753(2) 0.71782(6) 0.0362(4) Uani 1 1 d . . . . .
H24 H 0.8703 0.1666 0.7266 0.043 Uiso 1 1 calc R U . . .
C25 C 0.84870(11) 0.4023(3) 0.74858(6) 0.0382(4) Uani 1 1 d . . . . .
H25 H 0.8736 0.3813 0.7783 0.046 Uiso 1 1 calc R U . . .
C26 C 0.81384(10) 0.5609(2) 0.73566(5) 0.0351(4) Uani 1 1 d . . . . .
H26 H 0.8145 0.6486 0.7566 0.042 Uiso 1 1 calc R U . . .
C27 C 0.77810(9) 0.5911(2) 0.69235(5) 0.0296(4) Uani 1 1 d . . . . .
H27 H 0.7548 0.7002 0.6838 0.035 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
N1 C8 1.379(2) . ?
N1 C1 1.384(2) . ?
N1 C14 1.459(2) . ?
N2 C13 1.148(2) . ?
O1 C9 1.3572(18) . ?
O1 H1 0.8400 . ?
O2 C15 1.2170(19) . ?
C1 C2 1.398(2) . ?
C1 C6 1.407(2) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.407(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.439(2) . ?
C7 C8 1.405(2) . ?
C7 C12 1.413(2) . ?
C8 C9 1.405(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.417(2) . ?
C10 C15 1.510(2) . ?
C11 C12 1.395(2) . ?
C11 C22 1.489(2) . ?
C12 C13 1.435(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.486(2) . ?
C16 C17 1.389(2) . ?
C16 C21 1.396(2) . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.397(2) . ?
C22 C23 1.402(2) . ?
C23 C24 1.385(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.390(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
C8 N1 C1 108.10(13) . . ?
C8 N1 C14 128.08(14) . . ?
C1 N1 C14 123.64(14) . . ?
C9 O1 H1 109.5 . . ?
N1 C1 C2 128.42(16) . . ?
N1 C1 C6 109.68(14) . . ?
C2 C1 C6 121.89(15) . . ?
C3 C2 C1 117.30(16) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.52(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.38(16) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 118.44(17) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 119.43(15) . . ?
C5 C6 C7 134.58(16) . . ?
C1 C6 C7 105.96(14) . . ?
C8 C7 C12 119.75(14) . . ?
C8 C7 C6 106.99(13) . . ?
C12 C7 C6 133.21(14) . . ?
N1 C8 C7 109.25(13) . . ?
N1 C8 C9 130.15(14) . . ?
C7 C8 C9 120.59(14) . . ?
O1 C9 C10 123.72(13) . . ?
O1 C9 C8 117.64(13) . . ?
C10 C9 C8 118.61(14) . . ?
C9 C10 C11 122.11(14) . . ?
C9 C10 C15 116.59(13) . . ?
C11 C10 C15 121.28(13) . . ?
C12 C11 C10 118.44(14) . . ?
C12 C11 C22 121.97(13) . . ?
C10 C11 C22 119.56(13) . . ?
C11 C12 C7 120.48(14) . . ?
C11 C12 C13 121.97(14) . . ?
C7 C12 C13 117.53(13) . . ?
N2 C13 C12 175.35(17) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 C16 121.66(14) . . ?
O2 C15 C10 119.75(14) . . ?
C16 C15 C10 118.35(13) . . ?
C17 C16 C21 119.34(15) . . ?
C17 C16 C15 121.63(14) . . ?
C21 C16 C15 118.94(14) . . ?
C18 C17 C16 120.74(15) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.57(16) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.01(16) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.74(17) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C16 119.60(17) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C27 C22 C23 118.38(14) . . ?
C27 C22 C11 120.51(14) . . ?
C23 C22 C11 121.11(14) . . ?
C24 C23 C22 120.14(16) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 120.96(17) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 119.40(16) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 120.06(16) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C22 121.05(16) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -177.21(16) . . . . ?
C14 N1 C1 C2 -1.8(3) . . . . ?
C8 N1 C1 C6 1.36(18) . . . . ?
C14 N1 C1 C6 176.80(15) . . . . ?
N1 C1 C2 C3 177.22(16) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 1.7(2) . . . . ?
C4 C5 C6 C7 -175.96(17) . . . . ?
N1 C1 C6 C5 -179.16(14) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
N1 C1 C6 C7 -0.90(18) . . . . ?
C2 C1 C6 C7 177.78(15) . . . . ?
C5 C6 C7 C8 177.99(18) . . . . ?
C1 C6 C7 C8 0.11(17) . . . . ?
C5 C6 C7 C12 0.7(3) . . . . ?
C1 C6 C7 C12 -177.19(16) . . . . ?
C1 N1 C8 C7 -1.28(18) . . . . ?
C14 N1 C8 C7 -176.45(15) . . . . ?
C1 N1 C8 C9 177.19(16) . . . . ?
C14 N1 C8 C9 2.0(3) . . . . ?
C12 C7 C8 N1 178.45(14) . . . . ?
C6 C7 C8 N1 0.72(17) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
C6 C7 C8 C9 -177.93(14) . . . . ?
N1 C8 C9 O1 3.1(3) . . . . ?
C7 C8 C9 O1 -178.60(14) . . . . ?
N1 C8 C9 C10 -178.87(15) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
O1 C9 C10 C11 179.47(14) . . . . ?
C8 C9 C10 C11 1.5(2) . . . . ?
O1 C9 C10 C15 1.0(2) . . . . ?
C8 C9 C10 C15 -176.95(13) . . . . ?
C9 C10 C11 C12 -1.8(2) . . . . ?
C15 C10 C11 C12 176.65(14) . . . . ?
C9 C10 C11 C22 176.53(14) . . . . ?
C15 C10 C11 C22 -5.1(2) . . . . ?
C10 C11 C12 C7 1.0(2) . . . . ?
C22 C11 C12 C7 -177.27(14) . . . . ?
C10 C11 C12 C13 179.22(14) . . . . ?
C22 C11 C12 C13 1.0(2) . . . . ?
C8 C7 C12 C11 0.0(2) . . . . ?
C6 C7 C12 C11 176.99(16) . . . . ?
C8 C7 C12 C13 -178.36(14) . . . . ?
C6 C7 C12 C13 -1.3(3) . . . . ?
C9 C10 C15 O2 -71.54(19) . . . . ?
C11 C10 C15 O2 109.97(17) . . . . ?
C9 C10 C15 C16 102.89(16) . . . . ?
C11 C10 C15 C16 -75.61(18) . . . . ?
O2 C15 C16 C17 -177.25(14) . . . . ?
C10 C15 C16 C17 8.4(2) . . . . ?
O2 C15 C16 C21 6.3(2) . . . . ?
C10 C15 C16 C21 -168.00(14) . . . . ?
C21 C16 C17 C18 0.0(2) . . . . ?
C15 C16 C17 C18 -176.46(14) . . . . ?
C16 C17 C18 C19 0.0(2) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C16 0.3(3) . . . . ?
C17 C16 C21 C20 -0.1(3) . . . . ?
C15 C16 C21 C20 176.42(16) . . . . ?
C12 C11 C22 C27 129.11(16) . . . . ?
C10 C11 C22 C27 -49.1(2) . . . . ?
C12 C11 C22 C23 -51.0(2) . . . . ?
C10 C11 C22 C23 130.77(16) . . . . ?
C27 C22 C23 C24 0.4(2) . . . . ?
C11 C22 C23 C24 -179.44(14) . . . . ?
C22 C23 C24 C25 -0.4(2) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C25 C26 C27 C22 0.5(2) . . . . ?
C23 C22 C27 C26 -0.5(2) . . . . ?
C11 C22 C27 C26 179.37(14) . . . . ?

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
C14 H14A O1 0.98 2.32 2.925(2) 118.7 .
O1 H1 O2 0.84 2.45 3.0963(16) 134.2 .
O1 H1 N2 0.84 2.09 2.8059(18) 142.7 3_455
O1 H1 N2 0.84 2.09 2.8059(18) 142.7 3_455
O1 H1 O2 0.84 2.45 3.0963(16) 134.2 .
C14 H14A O1 0.98 2.32 2.925(2) 118.7 .

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-4

