# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_658
_database_code_depnum_ccdc_archive 'CCDC 1993548'
loop_
_audit_author_name
_audit_author_address
'Weiqing Weiqing Xie'
;Northwest Agriculture and Forstry University
China
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C31 H23 N O3'
_chemical_formula_sum            'C31 H23 N O3'
_chemical_formula_weight         457.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   14.9496(3)
_cell_length_b                   9.5237(2)
_cell_length_c                   17.4300(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.8310(10)
_cell_angle_gamma                90
_cell_volume                     2303.64(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7420
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      71.31

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            25350
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.337
_diffrn_reflns_theta_max         72.627
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4535
_reflns_number_gt                2994
_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-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0711P)²+0.2703P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4535
_refine_ls_number_parameters     317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1590
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.15978(10) 0.46449(14) 0.50530(9) 0.0519(4) Uani 1 1 d . . . . .
O2 O 0.07102(16) 0.06885(19) 0.62554(12) 0.0832(6) Uani 1 1 d . . . . .
O3 O 0.09951(13) 0.27090(18) 0.69185(10) 0.0669(4) Uani 1 1 d . . . . .
N1 N 0.25945(12) 0.30815(17) 0.46669(11) 0.0494(4) Uani 1 1 d . . . . .
C1 C 0.19963(19) -0.0534(2) 0.50697(16) 0.0657(6) Uani 1 1 d . . . . .
H1A H 0.148155 -0.102325 0.511837 0.079 Uiso 1 1 calc R U . . .
C2 C 0.2833(2) -0.1249(2) 0.51505(19) 0.0763(7) Uani 1 1 d . . . . .
H2A H 0.288424 -0.220883 0.525748 0.092 Uiso 1 1 calc R U . . .
C3 C 0.3586(2) -0.0519(3) 0.50702(17) 0.0732(7) Uani 1 1 d . . . . .
H3A H 0.415236 -0.099021 0.512788 0.088 Uiso 1 1 calc R U . . .
C4 C 0.35163(17) 0.0907(2) 0.49049(15) 0.0601(6) Uani 1 1 d . . . . .
H4A H 0.403131 0.138073 0.484684 0.072 Uiso 1 1 calc R U . . .
C5 C 0.26785(15) 0.1634(2) 0.48251(12) 0.0486(5) Uani 1 1 d . . . . .
C6 C 0.16737(14) 0.3783(2) 0.43727(12) 0.0478(5) Uani 1 1 d . . . . .
C7 C 0.08490(15) 0.2739(2) 0.41164(13) 0.0538(5) Uani 1 1 d . . . . .
H7A H 0.082292 0.223883 0.362385 0.065 Uiso 1 1 calc R U . . .
H7B H 0.024174 0.322574 0.399554 0.065 Uiso 1 1 calc R U . . .
C8 C 0.10190(15) 0.1717(2) 0.48237(13) 0.0516(5) Uani 1 1 d . . . . .
H8A H 0.046700 0.108181 0.469738 0.062 Uiso 1 1 calc R U . . .
C9 C 0.19126(16) 0.0892(2) 0.49181(13) 0.0524(5) Uani 1 1 d . . . . .
C10 C 0.11318(15) 0.2573(2) 0.55817(13) 0.0512(5) Uani 1 1 d . . . . .
C11 C 0.09368(17) 0.1905(3) 0.62440(15) 0.0605(6) Uani 1 1 d . . . . .
C12 C 0.12202(16) 0.4112(3) 0.69656(14) 0.0596(6) Uani 1 1 d . . . . .
C13 C 0.12287(19) 0.4833(3) 0.76556(16) 0.0766(7) Uani 1 1 d . . . . .
H13A H 0.108548 0.437334 0.806658 0.092 Uiso 1 1 calc R U . . .
C14 C 0.1451(2) 0.6240(4) 0.77276(18) 0.0821(8) Uani 1 1 d . . . . .
H14A H 0.144962 0.673285 0.818764 0.099 Uiso 1 1 calc R U . . .
C15 C 0.16770(18) 0.6930(3) 0.71273(18) 0.0758(8) Uani 1 1 d . . . . .
H15A H 0.182908 0.788122 0.718446 0.091 Uiso 1 1 calc R U . . .
C16 C 0.16761(16) 0.6206(2) 0.64430(16) 0.0617(6) Uani 1 1 d . . . . .
H16A H 0.183340 0.666959 0.604054 0.074 Uiso 1 1 calc R U . . .
C17 C 0.14402(14) 0.4778(2) 0.63493(13) 0.0525(5) Uani 1 1 d . . . . .
C18 C 0.13867(14) 0.3943(2) 0.56403(13) 0.0481(5) Uani 1 1 d . . . . .
C19 C 0.34511(15) 0.3906(2) 0.47456(14) 0.0527(5) Uani 1 1 d . . . . .
H19A H 0.324834 0.485776 0.456560 0.063 Uiso 1 1 calc R U . . .
H19B H 0.373083 0.351848 0.437095 0.063 Uiso 1 1 calc R U . . .
C20 C 0.42281(15) 0.3971(2) 0.56007(13) 0.0481(5) Uani 1 1 d . . . . .
C21 C 0.40397(17) 0.4501(2) 0.62649(15) 0.0602(6) Uani 1 1 d . . . . .
H21A H 0.341490 0.476333 0.619473 0.072 Uiso 1 1 calc R U . . .
C22 C 0.4770(2) 0.4644(3) 0.70313(16) 0.0697(7) Uani 1 1 d . . . . .
H22A H 0.463583 0.499422 0.747471 0.084 Uiso 1 1 calc R U . . .
C23 C 0.56967(18) 0.4267(3) 0.71370(15) 0.0664(6) Uani 1 1 d . . . . .
H23A H 0.618953 0.437320 0.765101 0.080 Uiso 1 1 calc R U . . .
C24 C 0.58958(17) 0.3736(2) 0.64887(15) 0.0625(6) Uani 1 1 d . . . . .
H24A H 0.652177 0.347395 0.656265 0.075 Uiso 1 1 calc R U . . .
C25 C 0.51662(15) 0.3591(2) 0.57259(14) 0.0550(5) Uani 1 1 d . . . . .
H25A H 0.530615 0.323155 0.528718 0.066 Uiso 1 1 calc R U . . .
C26 C 0.15698(15) 0.4807(2) 0.36748(13) 0.0537(5) Uani 1 1 d . . . . .
C27 C 0.1704(2) 0.4305(3) 0.29798(15) 0.0705(7) Uani 1 1 d . . . . .
H27A H 0.188840 0.337635 0.296395 0.085 Uiso 1 1 calc R U . . .
C28 C 0.1565(2) 0.5170(4) 0.23105(17) 0.0874(9) Uani 1 1 d . . . . .
H28A H 0.164721 0.482194 0.184262 0.105 Uiso 1 1 calc R U . . .
C29 C 0.1304(2) 0.6554(4) 0.2337(2) 0.0930(10) Uani 1 1 d . . . . .
H29A H 0.121652 0.714052 0.188806 0.112 Uiso 1 1 calc R U . . .
C30 C 0.1174(2) 0.7065(3) 0.3024(2) 0.0878(9) Uani 1 1 d . . . . .
H30A H 0.099834 0.799786 0.304215 0.105 Uiso 1 1 calc R U . . .
C31 C 0.13039(18) 0.6191(3) 0.36883(17) 0.0682(6) Uani 1 1 d . . . . .
H31A H 0.121103 0.653906 0.415155 0.082 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 C18 1.354(2) . ?
O1 C6 1.481(2) . ?
O2 C11 1.209(3) . ?
O3 C12 1.373(3) . ?
O3 C11 1.379(3) . ?
N1 C5 1.402(2) . ?
N1 C6 1.442(2) . ?
N1 C19 1.464(2) . ?
C1 C9 1.381(3) . ?
C1 C2 1.384(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.383(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.392(3) . ?
C4 H4A 0.9300 . ?
C5 C9 1.405(3) . ?
C6 C7 1.516(3) . ?
C6 C26 1.521(3) . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.505(3) . ?
C8 C10 1.508(3) . ?
C8 H8A 0.9800 . ?
C10 C18 1.352(3) . ?
C10 C11 1.440(3) . ?
C12 C13 1.381(3) . ?
C12 C17 1.388(3) . ?
C13 C14 1.374(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.380(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.400(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.446(3) . ?
C19 C20 1.512(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.384(3) . ?
C20 C25 1.385(3) . ?
C21 C22 1.383(3) . ?
C21 H21A 0.9300 . ?
C22 C23 1.375(4) . ?
C22 H22A 0.9300 . ?
C23 C24 1.368(4) . ?
C23 H23A 0.9300 . ?
C24 C25 1.378(3) . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9300 . ?
C26 C31 1.379(3) . ?
C26 C27 1.384(3) . ?
C27 C28 1.380(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.379(5) . ?
C28 H28A 0.9300 . ?
C29 C30 1.373(5) . ?
C29 H29A 0.9300 . ?
C30 C31 1.380(4) . ?
C30 H30A 0.9300 . ?
C31 H31A 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
C18 O1 C6 116.15(15) . . ?
C12 O3 C11 121.89(18) . . ?
C5 N1 C6 121.97(16) . . ?
C5 N1 C19 119.84(17) . . ?
C6 N1 C19 118.07(16) . . ?
C9 C1 C2 121.2(2) . . ?
C9 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2A 120.5 . . ?
C1 C2 H2A 120.5 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3A 119.4 . . ?
C4 C3 H3A 119.4 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C5 N1 121.37(19) . . ?
C4 C5 C9 118.64(19) . . ?
N1 C5 C9 119.99(19) . . ?
N1 C6 O1 108.63(15) . . ?
N1 C6 C7 111.40(16) . . ?
O1 C6 C7 107.65(16) . . ?
N1 C6 C26 112.43(17) . . ?
O1 C6 C26 105.64(16) . . ?
C7 C6 C26 110.78(17) . . ?
C6 C7 C8 108.02(16) . . ?
C6 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C10 112.39(17) . . ?
C9 C8 C7 107.31(17) . . ?
C10 C8 C7 107.20(17) . . ?
C9 C8 H8A 110.0 . . ?
C10 C8 H8A 110.0 . . ?
C7 C8 H8A 110.0 . . ?
C1 C9 C5 119.8(2) . . ?
C1 C9 C8 123.2(2) . . ?
C5 C9 C8 116.93(18) . . ?
C18 C10 C11 120.1(2) . . ?
C18 C10 C8 121.63(19) . . ?
C11 C10 C8 118.25(19) . . ?
O2 C11 O3 116.6(2) . . ?
O2 C11 C10 125.3(2) . . ?
O3 C11 C10 118.1(2) . . ?
O3 C12 C13 117.3(2) . . ?
O3 C12 C17 121.4(2) . . ?
C13 C12 C17 121.2(2) . . ?
C14 C13 C12 119.2(3) . . ?
C14 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?
C13 C14 C15 121.0(3) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 119.8(3) . . ?
C16 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16A 119.8 . . ?
C17 C16 H16A 119.8 . . ?
C12 C17 C16 118.4(2) . . ?
C12 C17 C18 117.2(2) . . ?
C16 C17 C18 124.4(2) . . ?
C10 C18 O1 123.87(19) . . ?
C10 C18 C17 121.27(19) . . ?
O1 C18 C17 114.86(18) . . ?
N1 C19 C20 116.03(17) . . ?
N1 C19 H19A 108.3 . . ?
C20 C19 H19A 108.3 . . ?
N1 C19 H19B 108.3 . . ?
C20 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C21 C20 C25 118.2(2) . . ?
C21 C20 C19 121.23(19) . . ?
C25 C20 C19 120.4(2) . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21A 119.7 . . ?
C20 C21 H21A 119.7 . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 H22A 120.1 . . ?
C21 C22 H22A 120.1 . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23A 119.9 . . ?
C22 C23 H23A 119.9 . . ?
C23 C24 C25 119.8(2) . . ?
C23 C24 H24A 120.1 . . ?
C25 C24 H24A 120.1 . . ?
C24 C25 C20 121.2(2) . . ?
C24 C25 H25A 119.4 . . ?
C20 C25 H25A 119.4 . . ?
C31 C26 C27 118.8(2) . . ?
C31 C26 C6 122.9(2) . . ?
C27 C26 C6 118.2(2) . . ?
C28 C27 C26 120.5(3) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C29 C28 C27 119.9(3) . . ?
C29 C28 H28A 120.1 . . ?
C27 C28 H28A 120.1 . . ?
C30 C29 C28 120.1(3) . . ?
C30 C29 H29A 120.0 . . ?
C28 C29 H29A 120.0 . . ?
C29 C30 C31 119.8(3) . . ?
C29 C30 H30A 120.1 . . ?
C31 C30 H30A 120.1 . . ?
C26 C31 C30 120.9(3) . . ?
C26 C31 H31A 119.5 . . ?
C30 C31 H31A 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
C9 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 N1 179.3(2) . . . . ?
C3 C4 C5 C9 0.2(3) . . . . ?
C6 N1 C5 C4 163.6(2) . . . . ?
C19 N1 C5 C4 -12.2(3) . . . . ?
C6 N1 C5 C9 -17.3(3) . . . . ?
C19 N1 C5 C9 166.91(19) . . . . ?
C5 N1 C6 O1 107.8(2) . . . . ?
C19 N1 C6 O1 -76.3(2) . . . . ?
C5 N1 C6 C7 -10.6(3) . . . . ?
C19 N1 C6 C7 165.27(18) . . . . ?
C5 N1 C6 C26 -135.63(19) . . . . ?
C19 N1 C6 C26 40.2(2) . . . . ?
C18 O1 C6 N1 -77.90(19) . . . . ?
C18 O1 C6 C7 42.9(2) . . . . ?
C18 O1 C6 C26 161.26(16) . . . . ?
N1 C6 C7 C8 51.7(2) . . . . ?
O1 C6 C7 C8 -67.3(2) . . . . ?
C26 C6 C7 C8 177.64(17) . . . . ?
C6 C7 C8 C9 -65.7(2) . . . . ?
C6 C7 C8 C10 55.2(2) . . . . ?
C2 C1 C9 C5 1.4(4) . . . . ?
C2 C1 C9 C8 179.9(2) . . . . ?
C4 C5 C9 C1 -1.2(3) . . . . ?
N1 C5 C9 C1 179.7(2) . . . . ?
C4 C5 C9 C8 -179.76(19) . . . . ?
N1 C5 C9 C8 1.1(3) . . . . ?
C10 C8 C9 C1 103.7(2) . . . . ?
C7 C8 C9 C1 -138.7(2) . . . . ?
C10 C8 C9 C5 -77.8(2) . . . . ?
C7 C8 C9 C5 39.8(2) . . . . ?
C9 C8 C10 C18 96.0(2) . . . . ?
C7 C8 C10 C18 -21.7(3) . . . . ?
C9 C8 C10 C11 -85.6(2) . . . . ?
C7 C8 C10 C11 156.74(19) . . . . ?
C12 O3 C11 O2 -178.2(2) . . . . ?
C12 O3 C11 C10 0.8(3) . . . . ?
C18 C10 C11 O2 -179.5(2) . . . . ?
C8 C10 C11 O2 2.0(4) . . . . ?
C18 C10 C11 O3 1.6(3) . . . . ?
C8 C10 C11 O3 -176.90(18) . . . . ?
C11 O3 C12 C13 177.9(2) . . . . ?
C11 O3 C12 C17 -2.7(3) . . . . ?
O3 C12 C13 C14 179.9(2) . . . . ?
C17 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
O3 C12 C17 C16 -179.1(2) . . . . ?
C13 C12 C17 C16 0.2(3) . . . . ?
O3 C12 C17 C18 2.3(3) . . . . ?
C13 C12 C17 C18 -178.4(2) . . . . ?
C15 C16 C17 C12 -0.8(3) . . . . ?
C15 C16 C17 C18 177.7(2) . . . . ?
C11 C10 C18 O1 178.85(18) . . . . ?
C8 C10 C18 O1 -2.7(3) . . . . ?
C11 C10 C18 C17 -2.0(3) . . . . ?
C8 C10 C18 C17 176.45(18) . . . . ?
C6 O1 C18 C10 -8.4(3) . . . . ?
C6 O1 C18 C17 172.33(16) . . . . ?
C12 C17 C18 C10 0.1(3) . . . . ?
C16 C17 C18 C10 -178.4(2) . . . . ?
C12 C17 C18 O1 179.33(17) . . . . ?
C16 C17 C18 O1 0.8(3) . . . . ?
C5 N1 C19 C20 -63.2(3) . . . . ?
C6 N1 C19 C20 120.9(2) . . . . ?
N1 C19 C20 C21 -58.9(3) . . . . ?
N1 C19 C20 C25 125.6(2) . . . . ?
C25 C20 C21 C22 0.0(3) . . . . ?
C19 C20 C21 C22 -175.6(2) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C21 C22 C23 C24 -0.7(4) . . . . ?
C22 C23 C24 C25 0.6(4) . . . . ?
C23 C24 C25 C20 -0.1(3) . . . . ?
C21 C20 C25 C24 -0.1(3) . . . . ?
C19 C20 C25 C24 175.44(19) . . . . ?
N1 C6 C26 C31 -127.5(2) . . . . ?
O1 C6 C26 C31 -9.2(3) . . . . ?
C7 C6 C26 C31 107.1(2) . . . . ?
N1 C6 C26 C27 55.7(3) . . . . ?
O1 C6 C26 C27 174.02(19) . . . . ?
C7 C6 C26 C27 -69.7(3) . . . . ?
C31 C26 C27 C28 -0.6(4) . . . . ?
C6 C26 C27 C28 176.4(2) . . . . ?
C26 C27 C28 C29 0.9(4) . . . . ?
C27 C28 C29 C30 -0.6(5) . . . . ?
C28 C29 C30 C31 0.0(5) . . . . ?
C27 C26 C31 C30 -0.1(4) . . . . ?
C6 C26 C31 C30 -176.9(2) . . . . ?
C29 C30 C31 C26 0.4(4) . . . . ?

_refine_diff_density_max         0.203
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_660
_database_code_depnum_ccdc_archive 'CCDC 1993549'
loop_
_audit_author_name
_audit_author_address
'Weiqing Weiqing Xie'
;Northwest Agriculture and Forstry University
China
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-05-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H23 N O2'
_chemical_formula_sum            'C28 H23 N O2'
_chemical_formula_weight         405.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   10.1842(6)
_cell_length_b                   20.0153(11)
_cell_length_c                   10.5231(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.242(4)
_cell_angle_gamma                90
_cell_volume                     2136.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2054
_cell_measurement_theta_min      4.42
_cell_measurement_theta_max      44.90

_exptl_crystal_description       sheet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.620
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            17833
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_av_R_equivalents  0.1281
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.418
_diffrn_reflns_theta_max         73.078
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.963
_reflns_number_total             4023
_reflns_number_gt                1318
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.1483P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0059(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4023
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2382
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.3359
_refine_ls_wR_factor_gt          0.2222
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_restrained_S_all      0.948
_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 0.4041(4) 0.7290(2) 0.4474(5) 0.0869(14) Uani 1 1 d . . . . .
O2 O 0.1920(6) 0.5291(4) 0.5329(9) 0.128(3) Uani 1 1 d . . . . .
N1 N 0.5933(5) 0.7378(2) 0.3333(6) 0.0770(15) Uani 1 1 d . . . . .
C1 C 0.8504(6) 0.6303(3) 0.4995(7) 0.0788(18) Uani 1 1 d . . . . .
H1A H 0.874950 0.613761 0.580861 0.095 Uiso 1 1 calc R U . . .
C2 C 0.9234(6) 0.6140(3) 0.3988(8) 0.090(2) Uani 1 1 d . . . . .
H2B H 0.995298 0.585400 0.412582 0.108 Uiso 1 1 calc R U . . .
C3 C 0.8906(6) 0.6397(3) 0.2788(8) 0.095(2) Uani 1 1 d . . . . .
H3A H 0.940158 0.628789 0.211733 0.114 Uiso 1 1 calc R U . . .
C4 C 0.7841(6) 0.6814(3) 0.2594(7) 0.0825(19) Uani 1 1 d . . . . .
H4A H 0.763490 0.699273 0.178461 0.099 Uiso 1 1 calc R U . . .
C5 C 0.7067(6) 0.6979(3) 0.3549(6) 0.0737(17) Uani 1 1 d . . . . .
C6 C 0.5255(6) 0.7660(3) 0.4360(7) 0.0774(18) Uani 1 1 d . . . . .
C7 C 0.6114(6) 0.7618(3) 0.5628(6) 0.0813(18) Uani 1 1 d . . . . .
H7A H 0.688734 0.789942 0.560611 0.098 Uiso 1 1 calc R U . . .
H7B H 0.562209 0.776450 0.632396 0.098 Uiso 1 1 calc R U . . .
C8 C 0.6521(6) 0.6887(3) 0.5810(7) 0.0804(18) Uani 1 1 d . . . . .
H8A H 0.700637 0.682929 0.665016 0.096 Uiso 1 1 calc R U . . .
C9 C 0.7405(6) 0.6714(3) 0.4784(6) 0.0732(17) Uani 1 1 d . . . . .
C10 C 0.5315(6) 0.6443(3) 0.5708(6) 0.0763(17) Uani 1 1 d . . . . .
C11 C 0.5315(7) 0.5812(3) 0.6212(6) 0.0832(19) Uani 1 1 d . . . . .
H11A H 0.609086 0.564768 0.663307 0.100 Uiso 1 1 calc R U . . .
C12 C 0.4197(7) 0.5407(3) 0.6117(7) 0.088(2) Uani 1 1 d . . . . .
H12A H 0.421823 0.498005 0.646619 0.105 Uiso 1 1 calc R U . . .
C13 C 0.3050(7) 0.5664(4) 0.5482(8) 0.091(2) Uani 1 1 d . . . . .
C14 C 0.3029(6) 0.6286(3) 0.4965(7) 0.090(2) Uani 1 1 d . . . . .
H14A H 0.225528 0.645007 0.453918 0.108 Uiso 1 1 calc R U . . .
C15 C 0.4145(6) 0.6673(3) 0.5070(7) 0.0816(19) Uani 1 1 d . . . . .
C16 C 0.5396(8) 0.7514(3) 0.2020(7) 0.093(2) Uani 1 1 d . . . . .
H16A H 0.605676 0.775204 0.158919 0.111 Uiso 1 1 calc R U . . .
H16B H 0.464023 0.780716 0.204331 0.111 Uiso 1 1 calc R U . . .
C17 C 0.4976(6) 0.6904(3) 0.1239(7) 0.0751(17) Uani 1 1 d . . . . .
C18 C 0.4642(7) 0.6316(3) 0.1768(7) 0.091(2) Uani 1 1 d . . . . .
H18A H 0.470657 0.627651 0.265208 0.109 Uiso 1 1 calc R U . . .
C19 C 0.4213(8) 0.5780(4) 0.1032(9) 0.103(2) Uani 1 1 d . . . . .
H19A H 0.399035 0.538076 0.141233 0.124 Uiso 1 1 calc R U . . .
C20 C 0.4117(8) 0.5839(4) -0.0265(9) 0.106(2) Uani 1 1 d . . . . .
H20A H 0.383056 0.547612 -0.076735 0.127 Uiso 1 1 calc R U . . .
C21 C 0.4433(8) 0.6419(4) -0.0838(8) 0.104(2) Uani 1 1 d . . . . .
H21A H 0.434994 0.645491 -0.172261 0.125 Uiso 1 1 calc R U . . .
C22 C 0.4878(7) 0.6954(4) -0.0088(7) 0.0864(19) Uani 1 1 d . . . . .
H22A H 0.511288 0.734964 -0.047098 0.104 Uiso 1 1 calc R U . . .
C23 C 0.4822(6) 0.8370(3) 0.4062(7) 0.0787(18) Uani 1 1 d . . . . .
C24 C 0.3559(6) 0.8588(3) 0.4232(7) 0.087(2) Uani 1 1 d . . . . .
H24A H 0.293999 0.829280 0.450861 0.104 Uiso 1 1 calc R U . . .
C25 C 0.3223(8) 0.9257(4) 0.3985(7) 0.093(2) Uani 1 1 d . . . . .
H25A H 0.237782 0.940032 0.411674 0.112 Uiso 1 1 calc R U . . .
C26 C 0.4085(8) 0.9704(4) 0.3560(8) 0.109(3) Uani 1 1 d . . . . .
H26A H 0.383674 1.014416 0.338317 0.131 Uiso 1 1 calc R U . . .
C27 C 0.5343(8) 0.9483(4) 0.3402(8) 0.108(3) Uani 1 1 d . . . . .
H27A H 0.595894 0.978016 0.312427 0.129 Uiso 1 1 calc R U . . .
C28 C 0.5699(7) 0.8825(3) 0.3650(7) 0.093(2) Uani 1 1 d . . . . .
H28A H 0.655295 0.868756 0.353502 0.111 Uiso 1 1 calc R U . . .
H2A H 0.212(12) 0.498(6) 0.539(13) 0.20(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C15 1.384(7) . ?
O1 C6 1.456(7) . ?
O2 C13 1.369(9) . ?
O2 H2A 0.65(11) . ?
N1 C5 1.405(7) . ?
N1 C6 1.449(8) . ?
N1 C16 1.465(8) . ?
C1 C2 1.388(9) . ?
C1 C9 1.391(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.376(9) . ?
C2 H2B 0.9300 . ?
C3 C4 1.370(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(8) . ?
C4 H4A 0.9300 . ?
C5 C9 1.417(8) . ?
C6 C23 1.512(8) . ?
C6 C7 1.530(8) . ?
C7 C8 1.528(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.508(8) . ?
C8 C10 1.512(8) . ?
C8 H8A 0.9800 . ?
C10 C11 1.369(8) . ?
C10 C15 1.392(8) . ?
C11 C12 1.393(9) . ?
C11 H11A 0.9300 . ?
C12 C13 1.391(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.358(9) . ?
C14 C15 1.372(8) . ?
C14 H14A 0.9300 . ?
C16 C17 1.512(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.358(9) . ?
C17 C22 1.394(9) . ?
C18 C19 1.372(9) . ?
C18 H18A 0.9300 . ?
C19 C20 1.365(10) . ?
C19 H19A 0.9300 . ?
C20 C21 1.359(10) . ?
C20 H20A 0.9300 . ?
C21 C22 1.381(9) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C28 1.373(8) . ?
C23 C24 1.386(8) . ?
C24 C25 1.400(8) . ?
C24 H24A 0.9300 . ?
C25 C26 1.358(10) . ?
C25 H25A 0.9300 . ?
C26 C27 1.379(10) . ?
C26 H26A 0.9300 . ?
C27 C28 1.386(9) . ?
C27 H27A 0.9300 . ?
C28 H28A 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
C15 O1 C6 117.4(5) . . ?
C13 O2 H2A 105(10) . . ?
C5 N1 C6 122.8(6) . . ?
C5 N1 C16 119.3(6) . . ?
C6 N1 C16 118.0(5) . . ?
C2 C1 C9 119.7(7) . . ?
C2 C1 H1A 120.1 . . ?
C9 C1 H1A 120.1 . . ?
C3 C2 C1 120.8(7) . . ?
C3 C2 H2B 119.6 . . ?
C1 C2 H2B 119.6 . . ?
C4 C3 C2 119.1(7) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 122.5(7) . . ?
C3 C4 H4A 118.7 . . ?
C5 C4 H4A 118.7 . . ?
C4 C5 N1 122.5(6) . . ?
C4 C5 C9 118.2(6) . . ?
N1 C5 C9 119.3(6) . . ?
N1 C6 O1 109.2(5) . . ?
N1 C6 C23 111.2(6) . . ?
O1 C6 C23 105.2(5) . . ?
N1 C6 C7 110.8(5) . . ?
O1 C6 C7 108.8(5) . . ?
C23 C6 C7 111.4(5) . . ?
C8 C7 C6 106.8(5) . . ?
C8 C7 H7A 110.4 . . ?
C6 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
C6 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C9 C8 C10 110.4(5) . . ?
C9 C8 C7 107.7(5) . . ?
C10 C8 C7 110.2(5) . . ?
C9 C8 H8A 109.5 . . ?
C10 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C1 C9 C5 119.6(6) . . ?
C1 C9 C8 123.1(6) . . ?
C5 C9 C8 117.3(5) . . ?
C11 C10 C15 117.6(6) . . ?
C11 C10 C8 122.9(6) . . ?
C15 C10 C8 119.5(6) . . ?
C10 C11 C12 122.5(7) . . ?
C10 C11 H11A 118.8 . . ?
C12 C11 H11A 118.8 . . ?
C13 C12 C11 117.7(6) . . ?
C13 C12 H12A 121.2 . . ?
C11 C12 H12A 121.2 . . ?
C14 C13 O2 118.1(7) . . ?
C14 C13 C12 120.9(6) . . ?
O2 C13 C12 121.0(7) . . ?
C13 C14 C15 120.2(7) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C14 C15 O1 116.0(6) . . ?
C14 C15 C10 121.2(6) . . ?
O1 C15 C10 122.8(6) . . ?
N1 C16 C17 115.2(6) . . ?
N1 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
N1 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C18 C17 C22 118.4(6) . . ?
C18 C17 C16 123.1(7) . . ?
C22 C17 C16 118.5(6) . . ?
C17 C18 C19 121.7(8) . . ?
C17 C18 H18A 119.1 . . ?
C19 C18 H18A 119.1 . . ?
C20 C19 C18 119.1(8) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C21 C20 C19 121.3(8) . . ?
C21 C20 H20A 119.3 . . ?
C19 C20 H20A 119.3 . . ?
C20 C21 C22 119.1(8) . . ?
C20 C21 H21A 120.4 . . ?
C22 C21 H21A 120.4 . . ?
C21 C22 C17 120.4(7) . . ?
C21 C22 H22A 119.8 . . ?
C17 C22 H22A 119.8 . . ?
C28 C23 C24 118.1(6) . . ?
C28 C23 C6 120.2(6) . . ?
C24 C23 C6 121.7(6) . . ?
C23 C24 C25 119.4(6) . . ?
C23 C24 H24A 120.3 . . ?
C25 C24 H24A 120.3 . . ?
C26 C25 C24 122.5(7) . . ?
C26 C25 H25A 118.7 . . ?
C24 C25 H25A 118.7 . . ?
C25 C26 C27 117.6(7) . . ?
C25 C26 H26A 121.2 . . ?
C27 C26 H26A 121.2 . . ?
C26 C27 C28 120.8(7) . . ?
C26 C27 H27A 119.6 . . ?
C28 C27 H27A 119.6 . . ?
C23 C28 C27 121.6(7) . . ?
C23 C28 H28A 119.2 . . ?
C27 C28 H28A 119.2 . . ?

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
C9 C1 C2 C3 2.0(10) . . . . ?
C1 C2 C3 C4 -0.4(10) . . . . ?
C2 C3 C4 C5 -1.2(10) . . . . ?
C3 C4 C5 N1 -176.4(6) . . . . ?
C3 C4 C5 C9 1.1(10) . . . . ?
C6 N1 C5 C4 -167.8(6) . . . . ?
C16 N1 C5 C4 12.7(9) . . . . ?
C6 N1 C5 C9 14.6(9) . . . . ?
C16 N1 C5 C9 -164.9(6) . . . . ?
C5 N1 C6 O1 -105.4(6) . . . . ?
C16 N1 C6 O1 74.1(7) . . . . ?
C5 N1 C6 C23 139.0(6) . . . . ?
C16 N1 C6 C23 -41.5(7) . . . . ?
C5 N1 C6 C7 14.5(8) . . . . ?
C16 N1 C6 C7 -166.0(5) . . . . ?
C15 O1 C6 N1 77.4(7) . . . . ?
C15 O1 C6 C23 -163.2(5) . . . . ?
C15 O1 C6 C7 -43.8(7) . . . . ?
N1 C6 C7 C8 -54.1(6) . . . . ?
O1 C6 C7 C8 66.0(6) . . . . ?
C23 C6 C7 C8 -178.5(5) . . . . ?
C6 C7 C8 C9 66.2(6) . . . . ?
C6 C7 C8 C10 -54.3(7) . . . . ?
C2 C1 C9 C5 -2.0(9) . . . . ?
C2 C1 C9 C8 176.9(6) . . . . ?
C4 C5 C9 C1 0.5(9) . . . . ?
N1 C5 C9 C1 178.1(5) . . . . ?
C4 C5 C9 C8 -178.5(5) . . . . ?
N1 C5 C9 C8 -0.8(8) . . . . ?
C10 C8 C9 C1 -98.1(7) . . . . ?
C7 C8 C9 C1 141.6(6) . . . . ?
C10 C8 C9 C5 80.9(7) . . . . ?
C7 C8 C9 C5 -39.5(7) . . . . ?
C9 C8 C10 C11 82.4(8) . . . . ?
C7 C8 C10 C11 -158.8(6) . . . . ?
C9 C8 C10 C15 -97.0(7) . . . . ?
C7 C8 C10 C15 21.8(9) . . . . ?
C15 C10 C11 C12 -0.7(10) . . . . ?
C8 C10 C11 C12 179.8(6) . . . . ?
C10 C11 C12 C13 0.0(10) . . . . ?
C11 C12 C13 C14 0.5(11) . . . . ?
C11 C12 C13 O2 178.7(7) . . . . ?
O2 C13 C14 C15 -178.6(7) . . . . ?
C12 C13 C14 C15 -0.4(12) . . . . ?
C13 C14 C15 O1 177.8(7) . . . . ?
C13 C14 C15 C10 -0.4(11) . . . . ?
C6 O1 C15 C14 -168.9(6) . . . . ?
C6 O1 C15 C10 9.3(9) . . . . ?
C11 C10 C15 C14 0.9(10) . . . . ?
C8 C10 C15 C14 -179.6(6) . . . . ?
C11 C10 C15 O1 -177.1(6) . . . . ?
C8 C10 C15 O1 2.4(10) . . . . ?
C5 N1 C16 C17 60.3(8) . . . . ?
C6 N1 C16 C17 -119.2(6) . . . . ?
N1 C16 C17 C18 23.7(9) . . . . ?
N1 C16 C17 C22 -158.9(6) . . . . ?
C22 C17 C18 C19 -0.2(10) . . . . ?
C16 C17 C18 C19 177.3(7) . . . . ?
C17 C18 C19 C20 -0.1(12) . . . . ?
C18 C19 C20 C21 -0.3(13) . . . . ?
C19 C20 C21 C22 1.0(12) . . . . ?
C20 C21 C22 C17 -1.3(10) . . . . ?
C18 C17 C22 C21 0.9(10) . . . . ?
C16 C17 C22 C21 -176.7(6) . . . . ?
N1 C6 C23 C28 -49.2(8) . . . . ?
O1 C6 C23 C28 -167.3(6) . . . . ?
C7 C6 C23 C28 75.0(8) . . . . ?
N1 C6 C23 C24 133.0(6) . . . . ?
O1 C6 C23 C24 14.9(9) . . . . ?
C7 C6 C23 C24 -102.9(7) . . . . ?
C28 C23 C24 C25 -0.1(11) . . . . ?
C6 C23 C24 C25 177.7(6) . . . . ?
C23 C24 C25 C26 1.1(12) . . . . ?
C24 C25 C26 C27 -1.5(13) . . . . ?
C25 C26 C27 C28 1.0(13) . . . . ?
C24 C23 C28 C27 -0.4(11) . . . . ?
C6 C23 C28 C27 -178.3(7) . . . . ?
C26 C27 C28 C23 -0.1(13) . . . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.058



