# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1_a
_audit_block_doi                 10.5517/ccdc.csd.cc2h8vvh
_database_code_depnum_ccdc_archive 'CCDC 2302427'
loop_
_audit_author_name
_audit_author_address
DCz
;wenzhou university
China
;
_audit_update_record             
;
2023-10-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT084_1_a                 
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.40 Report
RESPONSE: This is caused by the weak diffraction of the sample.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H17 N O2'
_chemical_formula_weight         387.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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/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                   8.9223(17)
_cell_length_b                   58.659(12)
_cell_length_c                   7.7793(15)
_cell_angle_alpha                90
_cell_angle_beta                 107.267(10)
_cell_angle_gamma                90
_cell_volume                     3888.0(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3452
_cell_measurement_theta_min      4.52
_cell_measurement_theta_max      59.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.662
_shelx_estimated_absorpt_T_min   0.879
_shelx_estimated_absorpt_T_max   0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22432
_diffrn_reflns_av_unetI/netI     0.1409
_diffrn_reflns_av_R_equivalents  0.1128
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -69
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.523
_diffrn_reflns_theta_max         67.330
_diffrn_reflns_theta_full        67.330
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             6723
_reflns_number_gt                3751
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0100P)²+50.0000P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6723
_refine_ls_number_parameters     445
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2024
_refine_ls_R_factor_gt           0.1541
_refine_ls_wR_factor_ref         0.3972
_refine_ls_wR_factor_gt          0.3238
_refine_ls_goodness_of_fit_ref   0.859
_refine_ls_restrained_S_all      0.859
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2330(5) 0.20648(10) 0.9991(8) 0.066(2) Uani 1 1 d G . . . .
C6 C 1.3062(7) 0.21837(10) 1.1561(7) 0.065(3) Uani 1 1 d G . . . .
C5 C 1.4567(7) 0.22701(10) 1.1839(9) 0.083(3) Uani 1 1 d G . . . .
H5 H 1.5056 0.2350 1.2890 0.100 Uiso 1 1 calc R U . . .
C4 C 1.5338(5) 0.22375(12) 1.0547(12) 0.091(4) Uani 1 1 d G . . . .
H4 H 1.6345 0.2295 1.0734 0.109 Uiso 1 1 calc R U . . .
C3 C 1.4606(8) 0.21186(13) 0.8977(10) 0.097(4) Uani 1 1 d G . . . .
H3 H 1.5123 0.2097 0.8112 0.117 Uiso 1 1 calc R U . . .
C2 C 1.3102(8) 0.20323(11) 0.8698(8) 0.073(3) Uani 1 1 d G . . . .
H2 H 1.2612 0.1953 0.7648 0.087 Uiso 1 1 calc R U . . .
C7 C 1.1930(6) 0.22009(10) 1.2547(8) 0.064(2) Uani 1 1 d G . . . .
C12 C 1.0595(7) 0.20895(10) 1.1500(6) 0.059(2) Uani 1 1 d G . . . .
C11 C 0.9260(6) 0.20793(10) 1.2068(8) 0.068(2) Uani 1 1 d G . . . .
H11 H 0.8367 0.2005 1.1367 0.082 Uiso 1 1 calc R U . . .
C10 C 0.9258(7) 0.21804(12) 1.3683(8) 0.082(3) Uani 1 1 d G . . . .
H10 H 0.8364 0.2174 1.4063 0.099 Uiso 1 1 calc R U . . .
C9 C 1.0592(9) 0.22917(12) 1.4731(7) 0.087(3) Uani 1 1 d G . . . .
H9 H 1.0591 0.2359 1.5812 0.105 Uiso 1 1 calc R U . . .
C8 C 1.1928(7) 0.23020(10) 1.4163(8) 0.079(3) Uani 1 1 d G . . . .
H8 H 1.2821 0.2376 1.4863 0.095 Uiso 1 1 calc R U . . .
C13 C 0.9721(6) 0.18851(9) 0.8534(7) 0.060(2) Uani 1 1 d G . . . .
C14 C 1.0020(5) 0.16620(9) 0.8130(7) 0.061(2) Uani 1 1 d G . . . .
H14 H 1.0954 0.1592 0.8765 0.073 Uiso 1 1 calc R U . . .
C15 C 0.8922(6) 0.15442(7) 0.6777(7) 0.060(2) Uani 1 1 d G . . . .
H15 H 0.9122 0.1395 0.6506 0.072 Uiso 1 1 calc R U . . .
C16 C 0.7526(5) 0.16495(8) 0.5828(6) 0.0534(19) Uani 1 1 d G . . . .
C17 C 0.7228(5) 0.18726(9) 0.6232(7) 0.063(2) Uani 1 1 d G . . . .
H17 H 0.6294 0.1943 0.5597 0.076 Uiso 1 1 calc R U . . .
C18 C 0.8325(6) 0.19904(7) 0.7585(8) 0.063(2) Uani 1 1 d G . . . .
H18 H 0.8125 0.2140 0.7855 0.076 Uiso 1 1 calc R U . . .
C19 C 0.4054(6) 0.12938(8) 0.1722(6) 0.057(2) Uani 1 1 d G . . . .
C20 C 0.4430(6) 0.15182(9) 0.1450(5) 0.063(2) Uani 1 1 d G . . . .
H20 H 0.3908 0.1593 0.0384 0.075 Uiso 1 1 calc R U . . .
C21 C 0.5585(6) 0.16316(7) 0.2771(7) 0.059(2) Uani 1 1 d G . . . .
H21 H 0.5837 0.1782 0.2589 0.070 Uiso 1 1 calc R U . . .
C22 C 0.6365(5) 0.15206(8) 0.4364(6) 0.054(2) Uani 1 1 d G . . . .
C23 C 0.5989(6) 0.12962(8) 0.4636(5) 0.055(2) Uani 1 1 d G . . . .
H23 H 0.6510 0.1222 0.5702 0.067 Uiso 1 1 calc R U . . .
C24 C 0.4833(6) 0.11828(7) 0.3315(7) 0.0512(19) Uani 1 1 d G . . . .
C25 C 0.4360(10) 0.09508(15) 0.3598(12) 0.059(2) Uani 1 1 d . . . . .
C26 C 0.3046(10) 0.08628(16) 0.2168(12) 0.065(2) Uani 1 1 d . . . . .
H26 H 0.2677 0.0717 0.2281 0.078 Uiso 1 1 calc R U . . .
C27 C 0.2367(12) 0.09806(17) 0.0738(13) 0.073(3) Uani 1 1 d . . . . .
H27 H 0.1523 0.0916 -0.0131 0.087 Uiso 1 1 calc R U . . .
C28 C 0.0779(7) 0.11400(8) 0.4602(8) 0.058(2) Uani 1 1 d G . . . .
C33 C 0.0058(6) 0.12743(10) 0.3114(7) 0.062(2) Uani 1 1 d G . . . .
C32 C 0.0624(8) 0.14918(9) 0.2965(7) 0.078(3) Uani 1 1 d G . . . .
H32 H 0.0142 0.1582 0.1969 0.093 Uiso 1 1 calc R U . . .
C31 C 0.1912(8) 0.15750(8) 0.4303(9) 0.078(3) Uani 1 1 d G . . . .
H31 H 0.2291 0.1721 0.4203 0.094 Uiso 1 1 calc R U . . .
C30 C 0.2633(6) 0.14407(10) 0.5791(8) 0.072(3) Uani 1 1 d G . . . .
H30 H 0.3495 0.1496 0.6686 0.086 Uiso 1 1 calc R U . . .
C29 C 0.2067(7) 0.12232(10) 0.5940(7) 0.065(2) Uani 1 1 d G . . . .
H29 H 0.2549 0.1133 0.6936 0.078 Uiso 1 1 calc R U . . .
C34 C -0.1218(7) 0.11417(9) 0.1976(8) 0.064(2) Uani 1 1 d G . . . .
C39 C -0.1231(6) 0.09389(10) 0.2895(6) 0.062(2) Uani 1 1 d G . . . .
C38 C -0.2355(8) 0.07736(9) 0.2158(9) 0.074(3) Uani 1 1 d G . . . .
H38 H -0.2364 0.0638 0.2773 0.088 Uiso 1 1 calc R U . . .
C37 C -0.3464(7) 0.08112(12) 0.0501(9) 0.086(3) Uani 1 1 d G . . . .
H37 H -0.4216 0.0701 0.0008 0.103 Uiso 1 1 calc R U . . .
C36 C -0.3451(7) 0.10140(13) -0.0418(7) 0.089(3) Uani 1 1 d G . . . .
H36 H -0.4193 0.1039 -0.1527 0.107 Uiso 1 1 calc R U . . .
C35 C -0.2327(8) 0.11792(10) 0.0319(8) 0.078(3) Uani 1 1 d G . . . .
H35 H -0.2318 0.1315 -0.0296 0.093 Uiso 1 1 calc R U . . .
C40 C 0.0262(6) 0.07670(9) 0.5876(6) 0.060(2) Uani 1 1 d G . . . .
C41 C -0.0902(5) 0.07154(9) 0.6671(7) 0.062(2) Uani 1 1 d G . . . .
H41 H -0.1880 0.0785 0.6260 0.074 Uiso 1 1 calc R U . . .
C42 C -0.0604(5) 0.05598(10) 0.8079(7) 0.058(2) Uani 1 1 d G . . . .
H42 H -0.1382 0.0525 0.8611 0.070 Uiso 1 1 calc R U . . .
C43 C 0.0858(6) 0.04557(9) 0.8694(6) 0.056(2) Uani 1 1 d G . . . .
C44 C 0.2022(5) 0.05073(9) 0.7899(7) 0.062(2) Uani 1 1 d G . . . .
H44 H 0.3000 0.0438 0.8310 0.074 Uiso 1 1 calc R U . . .
C45 C 0.1723(6) 0.06629(10) 0.6490(7) 0.065(2) Uani 1 1 d G . . . .
H45 H 0.2502 0.0697 0.5959 0.078 Uiso 1 1 calc R U . . .
C46 C 0.2070(8) 0.00309(12) 1.3383(8) 0.098(4) Uani 1 1 d G . . . .
C51 C 0.2741(7) -0.00088(9) 1.2011(11) 0.088(4) Uani 1 1 d G . . . .
C50 C 0.2305(6) 0.01234(10) 1.0459(9) 0.073(3) Uani 1 1 d G . . . .
H50 H 0.2754 0.0097 0.9541 0.088 Uiso 1 1 calc R U . . .
C49 C 0.1197(6) 0.02954(9) 1.0279(7) 0.061(2) Uani 1 1 d G . . . .
C48 C 0.0526(7) 0.03351(10) 1.1651(9) 0.073(3) Uani 1 1 d G . . . .
H48 H -0.0216 0.0450 1.1530 0.087 Uiso 1 1 calc R U . . .
C47 C 0.0962(8) 0.02028(13) 1.3203(7) 0.088(3) Uani 1 1 d G . . . .
H47 H 0.0513 0.0229 1.4121 0.105 Uiso 1 1 calc R U . . .
C52 C 0.3872(15) -0.0197(3) 1.219(3) 0.130(7) Uani 1 1 d . . . . .
C53 C 0.4290(18) -0.0295(3) 1.406(3) 0.148(9) Uani 1 1 d . . . . .
H53 H 0.5081 -0.0404 1.4368 0.177 Uiso 1 1 calc R U . . .
C54 C 0.362(2) -0.0239(4) 1.526(3) 0.170(11) Uani 1 1 d . U . . .
H54 H 0.3944 -0.0312 1.6374 0.203 Uiso 1 1 calc R U . . .
N1 N 1.0830(8) 0.20043(12) 0.9928(9) 0.0599(18) Uani 1 1 d . . . . .
N2 N -0.0035(8) 0.09355(13) 0.4457(9) 0.0619(19) Uani 1 1 d . . . . .
O1 O 0.2839(7) 0.11966(11) 0.0449(8) 0.0684(17) Uani 1 1 d . . . . .
O2 O 0.5036(8) 0.08398(11) 0.5019(9) 0.0739(18) Uani 1 1 d . . . . .
O3 O 0.4394(12) -0.02522(18) 1.095(2) 0.159(6) Uani 1 1 d . . . . .
O4 O 0.2473(10) -0.00771(16) 1.4995(12) 0.126(4) Uani 1 1 d . 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
C1 N1 1.371(8) . ?
C1 C6 1.3900 . ?
C1 C2 1.3900 . ?
C6 C5 1.3900 . ?
C6 C7 1.442(8) . ?
C5 C4 1.3900 . ?
C5 H5 0.9300 . ?
C4 C3 1.3900 . ?
C4 H4 0.9300 . ?
C3 C2 1.3900 . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 C12 1.3900 . ?
C7 C8 1.3900 . ?
C12 N1 1.393(8) . ?
C12 C11 1.3900 . ?
C11 C10 1.3900 . ?
C11 H11 0.9300 . ?
C10 C9 1.3900 . ?
C10 H10 0.9300 . ?
C9 C8 1.3900 . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C13 C14 1.3900 . ?
C13 C18 1.3900 . ?
C13 N1 1.417(7) . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 C17 1.3900 . ?
C16 C22 1.497(5) . ?
C17 C18 1.3900 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.358(6) . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C20 H20 0.9300 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 C25 1.461(10) . ?
C25 O2 1.271(10) . ?
C25 C26 1.451(11) . ?
C26 C27 1.297(12) . ?
C26 H26 0.9300 . ?
C27 O1 1.375(11) . ?
C27 H27 0.9300 . ?
C28 N2 1.389(9) . ?
C28 C33 1.3900 . ?
C28 C29 1.3900 . ?
C33 C32 1.3900 . ?
C33 C34 1.444(7) . ?
C32 C31 1.3900 . ?
C32 H32 0.9300 . ?
C31 C30 1.3900 . ?
C31 H31 0.9300 . ?
C30 C29 1.3900 . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
C34 C39 1.3900 . ?
C34 C35 1.3900 . ?
C39 N2 1.359(8) . ?
C39 C38 1.3900 . ?
C38 C37 1.3900 . ?
C38 H38 0.9300 . ?
C37 C36 1.3900 . ?
C37 H37 0.9300 . ?
C36 C35 1.3900 . ?
C36 H36 0.9300 . ?
C35 H35 0.9300 . ?
C40 C41 1.3900 . ?
C40 C45 1.3900 . ?
C40 N2 1.447(8) . ?
C41 C42 1.3900 . ?
C41 H41 0.9300 . ?
C42 C43 1.3900 . ?
C42 H42 0.9300 . ?
C43 C44 1.3900 . ?
C43 C49 1.508(6) . ?
C44 C45 1.3900 . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C46 O4 1.355(9) . ?
C46 C51 1.3900 . ?
C46 C47 1.3900 . ?
C51 C50 1.3900 . ?
C51 C52 1.473(17) . ?
C50 C49 1.3900 . ?
C50 H50 0.9300 . ?
C49 C48 1.3900 . ?
C48 C47 1.3900 . ?
C48 H48 0.9300 . ?
C47 H47 0.9300 . ?
C52 O3 1.23(2) . ?
C52 C53 1.50(3) . ?
C53 C54 1.29(3) . ?
C53 H53 0.9300 . ?
C54 O4 1.37(2) . ?
C54 H54 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
N1 C1 C6 111.1(5) . . ?
N1 C1 C2 128.8(5) . . ?
C6 C1 C2 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 133.5(5) . . ?
C1 C6 C7 106.4(5) . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C12 C7 C8 120.0 . . ?
C12 C7 C6 105.6(4) . . ?
C8 C7 C6 134.4(4) . . ?
N1 C12 C7 110.9(5) . . ?
N1 C12 C11 129.1(5) . . ?
C7 C12 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C14 C13 C18 120.0 . . ?
C14 C13 N1 120.0(4) . . ?
C18 C13 N1 120.0(4) . . ?
C13 C14 C15 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 C22 119.2(4) . . ?
C17 C16 C22 120.8(4) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.0 . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
O1 C19 C20 117.6(4) . . ?
O1 C19 C24 122.2(4) . . ?
C20 C19 C24 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 C16 119.4(4) . . ?
C23 C22 C16 120.4(4) . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 C25 121.2(5) . . ?
C19 C24 C25 118.7(5) . . ?
O2 C25 C26 123.5(8) . . ?
O2 C25 C24 121.6(7) . . ?
C26 C25 C24 114.8(8) . . ?
C27 C26 C25 122.3(9) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C26 C27 O1 122.9(8) . . ?
C26 C27 H27 118.6 . . ?
O1 C27 H27 118.6 . . ?
N2 C28 C33 108.7(4) . . ?
N2 C28 C29 131.3(5) . . ?
C33 C28 C29 120.0 . . ?
C32 C33 C28 120.0 . . ?
C32 C33 C34 133.1(4) . . ?
C28 C33 C34 106.9(4) . . ?
C33 C32 C31 120.0 . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C29 C30 C31 120.0 . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C29 C28 120.0 . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C39 C34 C35 120.0 . . ?
C39 C34 C33 105.7(4) . . ?
C35 C34 C33 134.2(4) . . ?
N2 C39 C34 110.3(5) . . ?
N2 C39 C38 129.6(5) . . ?
C34 C39 C38 120.0 . . ?
C37 C38 C39 120.0 . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C36 C35 120.0 . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C41 C40 C45 120.0 . . ?
C41 C40 N2 119.8(5) . . ?
C45 C40 N2 120.2(5) . . ?
C40 C41 C42 120.0 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C43 C42 C41 120.0 . . ?
C43 C42 H42 120.0 . . ?
C41 C42 H42 120.0 . . ?
C42 C43 C44 120.0 . . ?
C42 C43 C49 119.7(4) . . ?
C44 C43 C49 120.3(4) . . ?
C45 C44 C43 120.0 . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C40 120.0 . . ?
C44 C45 H45 120.0 . . ?
C40 C45 H45 120.0 . . ?
O4 C46 C51 125.2(8) . . ?
O4 C46 C47 114.7(8) . . ?
C51 C46 C47 120.0 . . ?
C50 C51 C46 120.0 . . ?
C50 C51 C52 120.6(10) . . ?
C46 C51 C52 119.4(10) . . ?
C51 C50 C49 120.0 . . ?
C51 C50 H50 120.0 . . ?
C49 C50 H50 120.0 . . ?
C48 C49 C50 120.0 . . ?
C48 C49 C43 119.7(4) . . ?
C50 C49 C43 119.9(4) . . ?
C49 C48 C47 120.0 . . ?
C49 C48 H48 120.0 . . ?
C47 C48 H48 120.0 . . ?
C48 C47 C46 120.0 . . ?
C48 C47 H47 120.0 . . ?
C46 C47 H47 120.0 . . ?
O3 C52 C53 127.8(16) . . ?
O3 C52 C51 121.9(15) . . ?
C53 C52 C51 110.3(17) . . ?
C54 C53 C52 124.5(17) . . ?
C54 C53 H53 117.8 . . ?
C52 C53 H53 117.8 . . ?
C53 C54 O4 123.6(18) . . ?
C53 C54 H54 118.2 . . ?
O4 C54 H54 118.2 . . ?
C1 N1 C12 106.0(5) . . ?
C1 N1 C13 127.4(7) . . ?
C12 N1 C13 126.6(6) . . ?
C39 N2 C28 108.2(6) . . ?
C39 N2 C40 127.5(6) . . ?
C28 N2 C40 123.8(6) . . ?
C27 O1 C19 119.0(6) . . ?
C46 O4 C54 116.6(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C6 C5 -176.8(6) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
N1 C1 C6 C7 -0.6(6) . . . . ?
C2 C1 C6 C7 176.2(5) . . . . ?
C1 C6 C5 C4 0.0 . . . . ?
C7 C6 C5 C4 -175.0(7) . . . . ?
C6 C5 C4 C3 0.0 . . . . ?
C5 C4 C3 C2 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
N1 C1 C2 C3 176.2(7) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C5 C6 C7 C12 175.8(4) . . . . ?
C1 C6 C7 C12 0.3(4) . . . . ?
C5 C6 C7 C8 -2.7(9) . . . . ?
C1 C6 C7 C8 -178.2(5) . . . . ?
C8 C7 C12 N1 178.9(6) . . . . ?
C6 C7 C12 N1 0.1(6) . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C6 C7 C12 C11 -178.8(5) . . . . ?
N1 C12 C11 C10 -178.6(7) . . . . ?
C7 C12 C11 C10 0.0 . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C6 C7 C8 C9 178.4(7) . . . . ?
C18 C13 C14 C15 0.0 . . . . ?
N1 C13 C14 C15 179.2(6) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C14 C15 C16 C22 179.5(5) . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C22 C16 C17 C18 -179.5(5) . . . . ?
C16 C17 C18 C13 0.0 . . . . ?
C14 C13 C18 C17 0.0 . . . . ?
N1 C13 C18 C17 -179.2(6) . . . . ?
O1 C19 C20 C21 175.3(6) . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C20 C21 C22 C16 -175.8(5) . . . . ?
C15 C16 C22 C21 -139.0(4) . . . . ?
C17 C16 C22 C21 40.4(6) . . . . ?
C15 C16 C22 C23 45.2(6) . . . . ?
C17 C16 C22 C23 -135.3(4) . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C16 C22 C23 C24 175.7(5) . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C22 C23 C24 C25 -177.0(6) . . . . ?
O1 C19 C24 C23 -175.0(6) . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
O1 C19 C24 C25 2.1(7) . . . . ?
C20 C19 C24 C25 177.1(6) . . . . ?
C23 C24 C25 O2 -3.5(11) . . . . ?
C19 C24 C25 O2 179.4(7) . . . . ?
C23 C24 C25 C26 174.7(6) . . . . ?
C19 C24 C25 C26 -2.4(9) . . . . ?
O2 C25 C26 C27 179.3(10) . . . . ?
C24 C25 C26 C27 1.2(14) . . . . ?
C25 C26 C27 O1 0.6(16) . . . . ?
N2 C28 C33 C32 178.1(6) . . . . ?
C29 C28 C33 C32 0.0 . . . . ?
N2 C28 C33 C34 -2.3(6) . . . . ?
C29 C28 C33 C34 179.6(5) . . . . ?
C28 C33 C32 C31 0.0 . . . . ?
C34 C33 C32 C31 -179.5(7) . . . . ?
C33 C32 C31 C30 0.0 . . . . ?
C32 C31 C30 C29 0.0 . . . . ?
C31 C30 C29 C28 0.0 . . . . ?
N2 C28 C29 C30 -177.6(7) . . . . ?
C33 C28 C29 C30 0.0 . . . . ?
C32 C33 C34 C39 -177.7(5) . . . . ?
C28 C33 C34 C39 2.8(5) . . . . ?
C32 C33 C34 C35 1.1(9) . . . . ?
C28 C33 C34 C35 -178.5(5) . . . . ?
C35 C34 C39 N2 178.8(6) . . . . ?
C33 C34 C39 N2 -2.3(6) . . . . ?
C35 C34 C39 C38 0.0 . . . . ?
C33 C34 C39 C38 179.0(5) . . . . ?
N2 C39 C38 C37 -178.5(7) . . . . ?
C34 C39 C38 C37 0.0 . . . . ?
C39 C38 C37 C36 0.0 . . . . ?
C38 C37 C36 C35 0.0 . . . . ?
C37 C36 C35 C34 0.0 . . . . ?
C39 C34 C35 C36 0.0 . . . . ?
C33 C34 C35 C36 -178.6(7) . . . . ?
C45 C40 C41 C42 0.0 . . . . ?
N2 C40 C41 C42 -177.6(6) . . . . ?
C40 C41 C42 C43 0.0 . . . . ?
C41 C42 C43 C44 0.0 . . . . ?
C41 C42 C43 C49 177.2(5) . . . . ?
C42 C43 C44 C45 0.0 . . . . ?
C49 C43 C44 C45 -177.1(5) . . . . ?
C43 C44 C45 C40 0.0 . . . . ?
C41 C40 C45 C44 0.0 . . . . ?
N2 C40 C45 C44 177.6(6) . . . . ?
O4 C46 C51 C50 -175.6(7) . . . . ?
C47 C46 C51 C50 0.0 . . . . ?
O4 C46 C51 C52 6.5(9) . . . . ?
C47 C46 C51 C52 -177.9(8) . . . . ?
C46 C51 C50 C49 0.0 . . . . ?
C52 C51 C50 C49 177.8(8) . . . . ?
C51 C50 C49 C48 0.0 . . . . ?
C51 C50 C49 C43 173.1(5) . . . . ?
C42 C43 C49 C48 -33.5(6) . . . . ?
C44 C43 C49 C48 143.7(4) . . . . ?
C42 C43 C49 C50 153.4(4) . . . . ?
C44 C43 C49 C50 -29.5(6) . . . . ?
C50 C49 C48 C47 0.0 . . . . ?
C43 C49 C48 C47 -173.1(5) . . . . ?
C49 C48 C47 C46 0.0 . . . . ?
O4 C46 C47 C48 176.1(6) . . . . ?
C51 C46 C47 C48 0.0 . . . . ?
C50 C51 C52 O3 -4.5(18) . . . . ?
C46 C51 C52 O3 173.4(12) . . . . ?
C50 C51 C52 C53 173.5(8) . . . . ?
C46 C51 C52 C53 -8.7(13) . . . . ?
O3 C52 C53 C54 -175(2) . . . . ?
C51 C52 C53 C54 7(2) . . . . ?
C52 C53 C54 O4 -2(3) . . . . ?
C6 C1 N1 C12 0.6(7) . . . . ?
C2 C1 N1 C12 -175.9(5) . . . . ?
C6 C1 N1 C13 179.0(6) . . . . ?
C2 C1 N1 C13 2.5(11) . . . . ?
C7 C12 N1 C1 -0.4(7) . . . . ?
C11 C12 N1 C1 178.3(5) . . . . ?
C7 C12 N1 C13 -178.8(6) . . . . ?
C11 C12 N1 C13 -0.1(11) . . . . ?
C14 C13 N1 C1 63.9(9) . . . . ?
C18 C13 N1 C1 -116.9(7) . . . . ?
C14 C13 N1 C12 -118.0(7) . . . . ?
C18 C13 N1 C12 61.2(9) . . . . ?
C34 C39 N2 C28 0.9(7) . . . . ?
C38 C39 N2 C28 179.5(5) . . . . ?
C34 C39 N2 C40 173.1(6) . . . . ?
C38 C39 N2 C40 -8.3(11) . . . . ?
C33 C28 N2 C39 0.9(7) . . . . ?
C29 C28 N2 C39 178.7(5) . . . . ?
C33 C28 N2 C40 -171.7(6) . . . . ?
C29 C28 N2 C40 6.1(11) . . . . ?
C41 C40 N2 C39 -55.1(9) . . . . ?
C45 C40 N2 C39 127.3(7) . . . . ?
C41 C40 N2 C28 116.1(7) . . . . ?
C45 C40 N2 C28 -61.5(9) . . . . ?
C26 C27 O1 C19 -1.1(14) . . . . ?
C20 C19 O1 C27 -175.5(7) . . . . ?
C24 C19 O1 C27 -0.3(10) . . . . ?
C51 C46 O4 C54 -0.6(13) . . . . ?
C47 C46 O4 C54 -176.5(10) . . . . ?
C53 C54 O4 C46 -2(3) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.132



####################################################################### 
# 
# 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_dmj8v23135_0m
_database_code_depnum_ccdc_archive 'CCDC 2302429'
loop_
_audit_author_name
_audit_author_address
BCz
;wenzhou university
China
;
_audit_update_record             
;
2023-10-20 deposited with the CCDC.	2024-12-09 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 H17 N O2'
_chemical_formula_weight         387.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   9.1866(3)
_cell_length_b                   16.3981(5)
_cell_length_c                   12.9389(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.972(2)
_cell_angle_gamma                90
_cell_volume                     1854.05(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      7.816
_cell_measurement_theta_max      109.828

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.442
_shelx_estimated_absorpt_T_min   0.937
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5283
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\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            18287
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.907
_diffrn_reflns_theta_max         55.000
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3504
_reflns_number_gt                3068
_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)+(0.0483P)²+0.5298P] 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       0.0146(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3504
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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 0.90621(16) -0.10667(8) 0.82488(13) 0.0841(5) Uani 1 1 d . . . . .
O2 O 1.06352(11) 0.12635(6) 0.82931(8) 0.0397(3) Uani 1 1 d . . . . .
N1 N 0.39832(12) 0.37529(6) 0.27730(9) 0.0297(3) Uani 1 1 d . . . . .
C1 C 1.14220(17) 0.06772(9) 0.89777(13) 0.0428(4) Uani 1 1 d . . . . .
H1 H 1.2364 0.0824 0.9481 0.051 Uiso 1 1 calc R U . . .
C2 C 1.09656(18) -0.00847(10) 0.89912(14) 0.0497(4) Uani 1 1 d . . . . .
H2 H 1.1596 -0.0454 0.9487 0.060 Uiso 1 1 calc R U . . .
C3 C 0.95218(18) -0.03656(9) 0.82641(14) 0.0476(4) Uani 1 1 d . . . . .
C4 C 0.86474(15) 0.02735(8) 0.75323(11) 0.0341(3) Uani 1 1 d . . . . .
C5 C 0.72134(16) 0.01235(8) 0.67807(12) 0.0380(3) Uani 1 1 d . . . . .
H5 H 0.6760 -0.0393 0.6756 0.046 Uiso 1 1 calc R U . . .
C6 C 0.64622(15) 0.07212(8) 0.60799(11) 0.0354(3) Uani 1 1 d . . . . .
H6 H 0.5497 0.0607 0.5582 0.042 Uiso 1 1 calc R U . . .
C7 C 0.71001(14) 0.15046(8) 0.60865(10) 0.0296(3) Uani 1 1 d . . . . .
C8 C 0.85079(15) 0.16656(8) 0.68504(11) 0.0322(3) Uani 1 1 d . . . . .
H8 H 0.8953 0.2185 0.6889 0.039 Uiso 1 1 calc R U . . .
C9 C 0.92534(14) 0.10498(8) 0.75584(10) 0.0306(3) Uani 1 1 d . . . . .
C10 C 0.62989(14) 0.21215(7) 0.52666(10) 0.0291(3) Uani 1 1 d . . . . .
C11 C 0.47156(14) 0.20837(8) 0.47890(11) 0.0301(3) Uani 1 1 d . . . . .
H11 H 0.4154 0.1681 0.5019 0.036 Uiso 1 1 calc R U . . .
C12 C 0.39551(14) 0.26252(8) 0.39851(11) 0.0302(3) Uani 1 1 d . . . . .
H12 H 0.2885 0.2595 0.3685 0.036 Uiso 1 1 calc R U . . .
C13 C 0.47642(14) 0.32137(7) 0.36190(10) 0.0281(3) Uani 1 1 d . . . . .
C14 C 0.63448(15) 0.32627(8) 0.40873(11) 0.0309(3) Uani 1 1 d . . . . .
H14 H 0.6904 0.3660 0.3846 0.037 Uiso 1 1 calc R U . . .
C15 C 0.70942(14) 0.27289(8) 0.49059(11) 0.0317(3) Uani 1 1 d . . . . .
H15 H 0.8159 0.2775 0.5226 0.038 Uiso 1 1 calc R U . . .
C16 C 0.28985(14) 0.35217(8) 0.17947(10) 0.0289(3) Uani 1 1 d . . . . .
C17 C 0.23736(15) 0.27456(8) 0.14248(11) 0.0334(3) Uani 1 1 d . . . . .
H17 H 0.2721 0.2280 0.1853 0.040 Uiso 1 1 calc R U . . .
C18 C 0.13186(15) 0.26901(9) 0.03995(12) 0.0374(3) Uani 1 1 d . . . . .
H18 H 0.0932 0.2175 0.0132 0.045 Uiso 1 1 calc R U . . .
C19 C 0.08128(16) 0.33755(9) -0.02481(12) 0.0398(4) Uani 1 1 d . . . . .
H19 H 0.0115 0.3314 -0.0948 0.048 Uiso 1 1 calc R U . . .
C20 C 0.13270(15) 0.41449(9) 0.01279(11) 0.0365(3) Uani 1 1 d . . . . .
H20 H 0.0978 0.4607 -0.0308 0.044 Uiso 1 1 calc R U . . .
C21 C 0.23743(14) 0.42242(8) 0.11679(11) 0.0302(3) Uani 1 1 d . . . . .
C22 C 0.31329(14) 0.49152(8) 0.18042(10) 0.0305(3) Uani 1 1 d . . . . .
C23 C 0.30278(16) 0.57543(8) 0.16435(12) 0.0377(3) Uani 1 1 d . . . . .
H23 H 0.2386 0.5972 0.0989 0.045 Uiso 1 1 calc R U . . .
C24 C 0.38777(18) 0.62638(9) 0.24566(13) 0.0431(4) Uani 1 1 d . . . . .
H24 H 0.3808 0.6832 0.2356 0.052 Uiso 1 1 calc R U . . .
C25 C 0.48370(17) 0.59434(9) 0.34247(13) 0.0408(4) Uani 1 1 d . . . . .
H25 H 0.5399 0.6301 0.3970 0.049 Uiso 1 1 calc R U . . .
C26 C 0.49838(16) 0.51104(8) 0.36049(11) 0.0339(3) Uani 1 1 d . . . . .
H26 H 0.5643 0.4898 0.4256 0.041 Uiso 1 1 calc R U . . .
C27 C 0.41187(14) 0.46016(7) 0.27856(10) 0.0290(3) Uani 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 C3 1.2227(19) . ?
O2 C1 1.3550(17) . ?
O2 C9 1.3760(15) . ?
N1 C27 1.3968(16) . ?
N1 C16 1.4003(16) . ?
N1 C13 1.4178(16) . ?
C1 C2 1.320(2) . ?
C1 H1 0.9400 . ?
C2 C3 1.445(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.4733(19) . ?
C4 C9 1.3856(19) . ?
C4 C5 1.3968(19) . ?
C5 C6 1.3685(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4109(18) . ?
C6 H6 0.9400 . ?
C7 C8 1.3894(18) . ?
C7 C10 1.4862(17) . ?
C8 C9 1.3932(18) . ?
C8 H8 0.9400 . ?
C10 C11 1.3953(17) . ?
C10 C15 1.3979(18) . ?
C11 C12 1.3821(18) . ?
C11 H11 0.9400 . ?
C12 C13 1.3876(18) . ?
C12 H12 0.9400 . ?
C13 C14 1.3925(18) . ?
C14 C15 1.3827(18) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 C17 1.3924(18) . ?
C16 C21 1.4056(18) . ?
C17 C18 1.3835(19) . ?
C17 H17 0.9400 . ?
C18 C19 1.393(2) . ?
C18 H18 0.9400 . ?
C19 C20 1.382(2) . ?
C19 H19 0.9400 . ?
C20 C21 1.3980(18) . ?
C20 H20 0.9400 . ?
C21 C22 1.4469(18) . ?
C22 C23 1.3904(19) . ?
C22 C27 1.4098(18) . ?
C23 C24 1.381(2) . ?
C23 H23 0.9400 . ?
C24 C25 1.393(2) . ?
C24 H24 0.9400 . ?
C25 C26 1.3852(19) . ?
C25 H25 0.9400 . ?
C26 C27 1.3898(18) . ?
C26 H26 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 O2 C9 117.59(11) . . ?
C27 N1 C16 108.44(10) . . ?
C27 N1 C13 126.17(10) . . ?
C16 N1 C13 125.35(10) . . ?
C2 C1 O2 124.95(13) . . ?
C2 C1 H1 117.5 . . ?
O2 C1 H1 117.5 . . ?
C1 C2 C3 121.66(14) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
O1 C3 C2 123.61(14) . . ?
O1 C3 C4 122.77(14) . . ?
C2 C3 C4 113.62(13) . . ?
C9 C4 C5 117.66(12) . . ?
C9 C4 C3 120.17(12) . . ?
C5 C4 C3 122.16(13) . . ?
C6 C5 C4 120.64(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.63(12) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 118.10(12) . . ?
C8 C7 C10 121.71(12) . . ?
C6 C7 C10 120.14(11) . . ?
C7 C8 C9 119.39(12) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O2 C9 C4 121.93(12) . . ?
O2 C9 C8 115.54(11) . . ?
C4 C9 C8 122.53(12) . . ?
C11 C10 C15 117.69(11) . . ?
C11 C10 C7 120.32(11) . . ?
C15 C10 C7 121.91(11) . . ?
C12 C11 C10 121.37(12) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.28(12) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 119.21(11) . . ?
C12 C13 N1 120.03(11) . . ?
C14 C13 N1 120.75(11) . . ?
C15 C14 C13 120.18(12) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 121.25(12) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C17 C16 N1 129.24(12) . . ?
C17 C16 C21 122.01(12) . . ?
N1 C16 C21 108.74(11) . . ?
C18 C17 C16 117.10(13) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
C17 C18 C19 121.91(13) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C20 C19 C18 120.69(13) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 118.87(13) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C16 119.38(12) . . ?
C20 C21 C22 133.49(12) . . ?
C16 C21 C22 107.12(11) . . ?
C23 C22 C27 119.43(12) . . ?
C23 C22 C21 133.70(12) . . ?
C27 C22 C21 106.83(11) . . ?
C24 C23 C22 119.20(13) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 120.58(13) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 121.67(13) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C27 117.42(13) . . ?
C25 C26 H26 121.3 . . ?
C27 C26 H26 121.3 . . ?
C26 C27 N1 129.42(12) . . ?
C26 C27 C22 121.68(12) . . ?
N1 C27 C22 108.83(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O2 C1 C2 0.2(2) . . . . ?
O2 C1 C2 C3 -1.2(3) . . . . ?
C1 C2 C3 O1 179.7(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
O1 C3 C4 C9 -177.51(18) . . . . ?
C2 C3 C4 C9 2.2(2) . . . . ?
O1 C3 C4 C5 1.2(3) . . . . ?
C2 C3 C4 C5 -179.09(15) . . . . ?
C9 C4 C5 C6 1.6(2) . . . . ?
C3 C4 C5 C6 -177.07(15) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 -1.8(2) . . . . ?
C5 C6 C7 C10 176.01(13) . . . . ?
C6 C7 C8 C9 1.59(19) . . . . ?
C10 C7 C8 C9 -176.14(12) . . . . ?
C1 O2 C9 C4 2.11(19) . . . . ?
C1 O2 C9 C8 -178.17(12) . . . . ?
C5 C4 C9 O2 177.90(13) . . . . ?
C3 C4 C9 O2 -3.4(2) . . . . ?
C5 C4 C9 C8 -1.8(2) . . . . ?
C3 C4 C9 C8 176.93(14) . . . . ?
C7 C8 C9 O2 -179.54(12) . . . . ?
C7 C8 C9 C4 0.2(2) . . . . ?
C8 C7 C10 C11 -156.33(13) . . . . ?
C6 C7 C10 C11 25.99(19) . . . . ?
C8 C7 C10 C15 26.99(19) . . . . ?
C6 C7 C10 C15 -150.69(13) . . . . ?
C15 C10 C11 C12 0.15(19) . . . . ?
C7 C10 C11 C12 -176.68(12) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C11 C12 C13 C14 -1.36(19) . . . . ?
C11 C12 C13 N1 178.23(11) . . . . ?
C27 N1 C13 C12 129.94(14) . . . . ?
C16 N1 C13 C12 -47.61(18) . . . . ?
C27 N1 C13 C14 -50.48(18) . . . . ?
C16 N1 C13 C14 131.97(13) . . . . ?
C12 C13 C14 C15 0.10(19) . . . . ?
N1 C13 C14 C15 -179.49(12) . . . . ?
C13 C14 C15 C10 1.3(2) . . . . ?
C11 C10 C15 C14 -1.43(19) . . . . ?
C7 C10 C15 C14 175.34(12) . . . . ?
C27 N1 C16 C17 -179.30(13) . . . . ?
C13 N1 C16 C17 -1.4(2) . . . . ?
C27 N1 C16 C21 1.73(14) . . . . ?
C13 N1 C16 C21 179.65(11) . . . . ?
N1 C16 C17 C18 -178.06(13) . . . . ?
C21 C16 C17 C18 0.8(2) . . . . ?
C16 C17 C18 C19 0.9(2) . . . . ?
C17 C18 C19 C20 -1.6(2) . . . . ?
C18 C19 C20 C21 0.5(2) . . . . ?
C19 C20 C21 C16 1.2(2) . . . . ?
C19 C20 C21 C22 179.99(14) . . . . ?
C17 C16 C21 C20 -1.87(19) . . . . ?
N1 C16 C21 C20 177.19(11) . . . . ?
C17 C16 C21 C22 179.04(12) . . . . ?
N1 C16 C21 C22 -1.90(14) . . . . ?
C20 C21 C22 C23 4.8(3) . . . . ?
C16 C21 C22 C23 -176.31(15) . . . . ?
C20 C21 C22 C27 -177.54(14) . . . . ?
C16 C21 C22 C27 1.36(14) . . . . ?
C27 C22 C23 C24 -0.9(2) . . . . ?
C21 C22 C23 C24 176.58(14) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C23 C24 C25 C26 0.5(2) . . . . ?
C24 C25 C26 C27 -0.8(2) . . . . ?
C25 C26 C27 N1 -176.27(13) . . . . ?
C25 C26 C27 C22 0.3(2) . . . . ?
C16 N1 C27 C26 176.10(13) . . . . ?
C13 N1 C27 C26 -1.8(2) . . . . ?
C16 N1 C27 C22 -0.85(14) . . . . ?
C13 N1 C27 C22 -178.75(11) . . . . ?
C23 C22 C27 C26 0.52(19) . . . . ?
C21 C22 C27 C26 -177.55(12) . . . . ?
C23 C22 C27 N1 177.74(12) . . . . ?
C21 C22 C27 N1 -0.32(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
C17 H17 O1 0.94 2.55 3.1372(18) 120.5 3_656

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.034

_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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2302428'
loop_
_audit_author_name
_audit_author_address
CTPA
;wenzhou university
China
;
_audit_update_record             
;
2023-10-20 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 N O2'
_chemical_formula_weight         389.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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/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                   13.484(3)
_cell_length_b                   14.809(3)
_cell_length_c                   10.7013(18)
_cell_angle_alpha                90
_cell_angle_beta                 110.737(10)
_cell_angle_gamma                90
_cell_volume                     1998.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4074
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      66.45

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.645
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15905
_diffrn_reflns_av_unetI/netI     0.0976
_diffrn_reflns_av_R_equivalents  0.1375
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.505
_diffrn_reflns_theta_max         67.719
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3543
_reflns_number_gt                2098
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1786P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3543
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0896
_refine_ls_wR_factor_ref         0.2854
_refine_ls_wR_factor_gt          0.2321
_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
C1 C 0.8623(3) 0.3952(2) 0.7152(3) 0.0572(8) Uani 1 1 d . . . . .
C2 C 0.9234(3) 0.3306(2) 0.6838(3) 0.0667(10) Uani 1 1 d . . . . .
H2 H 0.9590 0.3448 0.6262 0.080 Uiso 1 1 calc R U . . .
C3 C 0.9319(4) 0.2449(3) 0.7379(3) 0.0752(11) Uani 1 1 d . . . . .
H3 H 0.9721 0.2014 0.7149 0.090 Uiso 1 1 calc R U . . .
C4 C 0.8819(4) 0.2236(3) 0.8247(3) 0.0736(11) Uani 1 1 d . . . . .
H4 H 0.8881 0.1658 0.8606 0.088 Uiso 1 1 calc R U . . .
C5 C 0.8224(3) 0.2876(3) 0.8589(4) 0.0738(11) Uani 1 1 d . . . . .
H5 H 0.7885 0.2731 0.9183 0.089 Uiso 1 1 calc R U . . .
C6 C 0.8127(3) 0.3733(3) 0.8055(3) 0.0673(10) Uani 1 1 d . . . . .
H6 H 0.7730 0.4166 0.8297 0.081 Uiso 1 1 calc R U . . .
C7 C 0.8434(3) 0.5600(2) 0.7227(3) 0.0598(9) Uani 1 1 d . . . . .
C8 C 0.9052(3) 0.5676(3) 0.8568(3) 0.0710(10) Uani 1 1 d . . . . .
H8 H 0.9518 0.5213 0.8982 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8990(4) 0.6425(3) 0.9301(4) 0.0812(12) Uani 1 1 d . . . . .
H9 H 0.9406 0.6458 1.0203 0.097 Uiso 1 1 calc R U . . .
C10 C 0.8322(4) 0.7118(3) 0.8714(4) 0.0831(13) Uani 1 1 d . . . . .
H10 H 0.8272 0.7618 0.9213 0.100 Uiso 1 1 calc R U . . .
C11 C 0.7719(4) 0.7069(3) 0.7364(4) 0.0797(12) Uani 1 1 d . . . . .
H11 H 0.7277 0.7547 0.6952 0.096 Uiso 1 1 calc R U . . .
C12 C 0.7769(3) 0.6314(2) 0.6625(3) 0.0657(9) Uani 1 1 d . . . . .
H12 H 0.7356 0.6286 0.5721 0.079 Uiso 1 1 calc R U . . .
C13 C 0.8020(3) 0.4809(2) 0.5085(3) 0.0591(9) Uani 1 1 d . . . . .
C14 C 0.8439(3) 0.5324(2) 0.4310(3) 0.0671(10) Uani 1 1 d . . . . .
H14 H 0.9036 0.5678 0.4722 0.080 Uiso 1 1 calc R U . . .
C15 C 0.7983(3) 0.5317(2) 0.2938(3) 0.0666(10) Uani 1 1 d . . . . .
H15 H 0.8268 0.5677 0.2438 0.080 Uiso 1 1 calc R U . . .
C16 C 0.7100(3) 0.4781(2) 0.2286(3) 0.0600(9) Uani 1 1 d . . . . .
C17 C 0.6693(3) 0.4260(2) 0.3070(3) 0.0591(9) Uani 1 1 d . . . . .
H17 H 0.6105 0.3897 0.2659 0.071 Uiso 1 1 calc R U . . .
C18 C 0.7142(3) 0.4270(2) 0.4445(3) 0.0605(9) Uani 1 1 d . . . . .
H18 H 0.6856 0.3913 0.4947 0.073 Uiso 1 1 calc R U . . .
C19 C 0.5740(3) 0.4677(2) -0.1979(3) 0.0557(9) Uani 1 1 d . . . . .
C20 C 0.6193(3) 0.5474(2) -0.1361(3) 0.0640(9) Uani 1 1 d . . . . .
H20 H 0.6211 0.5981 -0.1865 0.077 Uiso 1 1 calc R U . . .
C21 C 0.6614(3) 0.5503(3) 0.0008(3) 0.0638(9) Uani 1 1 d . . . . .
H21 H 0.6910 0.6040 0.0425 0.077 Uiso 1 1 calc R U . . .
C22 C 0.6613(3) 0.4747(2) 0.0801(3) 0.0585(9) Uani 1 1 d . . . . .
C23 C 0.6138(3) 0.3968(2) 0.0149(3) 0.0602(9) Uani 1 1 d . . . . .
H23 H 0.6116 0.3462 0.0653 0.072 Uiso 1 1 calc R U . . .
C24 C 0.5692(3) 0.3916(2) -0.1243(3) 0.0570(9) Uani 1 1 d . . . . .
C25 C 0.5197(3) 0.3087(3) -0.1940(3) 0.0695(10) Uani 1 1 d . . . . .
C26 C 0.4848(4) 0.3143(3) -0.3384(3) 0.0757(11) Uani 1 1 d . . . . .
H26 H 0.4538 0.2640 -0.3895 0.091 Uiso 1 1 calc R U . . .
C27 C 0.4960(3) 0.3894(3) -0.3988(3) 0.0721(11) Uani 1 1 d . . . . .
H27 H 0.4736 0.3888 -0.4916 0.087 Uiso 1 1 calc R U . . .
N1 N 0.8494(3) 0.48110(19) 0.6515(2) 0.0647(8) Uani 1 1 d . . . . .
O1 O 0.5378(2) 0.46730(17) -0.33556(19) 0.0668(7) Uani 1 1 d . . . . .
O2 O 0.5090(3) 0.2403(2) -0.1345(2) 0.0877(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(5) . ?
C1 C6 1.394(4) . ?
C1 N1 1.425(4) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.386(5) . ?
C7 C12 1.389(5) . ?
C7 N1 1.413(4) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.387(4) . ?
C13 C18 1.390(5) . ?
C13 N1 1.434(4) . ?
C14 C15 1.376(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.395(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(4) . ?
C16 C22 1.490(4) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.378(3) . ?
C19 C20 1.384(5) . ?
C19 C24 1.390(4) . ?
C20 C21 1.372(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.405(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.383(5) . ?
C23 C24 1.397(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.469(5) . ?
C25 O2 1.232(4) . ?
C25 C26 1.449(4) . ?
C26 C27 1.323(5) . ?
C26 H26 0.9300 . ?
C27 O1 1.354(4) . ?
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
C2 C1 C6 118.8(3) . . ?
C2 C1 N1 119.0(3) . . ?
C6 C1 N1 122.2(3) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C12 118.1(3) . . ?
C8 C7 N1 119.9(3) . . ?
C12 C7 N1 122.0(3) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.3(4) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C14 C13 C18 118.5(3) . . ?
C14 C13 N1 121.0(3) . . ?
C18 C13 N1 120.5(3) . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 117.6(3) . . ?
C17 C16 C22 120.4(3) . . ?
C15 C16 C22 122.0(3) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 120.5(3) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O1 C19 C20 116.4(3) . . ?
O1 C19 C24 122.1(3) . . ?
C20 C19 C24 121.4(3) . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 122.1(3) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C23 C22 C21 117.4(3) . . ?
C23 C22 C16 121.1(3) . . ?
C21 C22 C16 121.5(3) . . ?
C22 C23 C24 122.1(3) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C19 C24 C23 118.1(3) . . ?
C19 C24 C25 119.6(3) . . ?
C23 C24 C25 122.3(3) . . ?
O2 C25 C26 123.0(4) . . ?
O2 C25 C24 122.7(3) . . ?
C26 C25 C24 114.3(3) . . ?
C27 C26 C25 121.2(4) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 O1 124.9(3) . . ?
C26 C27 H27 117.6 . . ?
O1 C27 H27 117.6 . . ?
C7 N1 C1 120.1(2) . . ?
C7 N1 C13 119.2(3) . . ?
C1 N1 C13 116.2(3) . . ?
C27 O1 C19 117.7(3) . . ?

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 2.2(6) . . . . ?
N1 C1 C2 C3 -176.0(4) . . . . ?
C1 C2 C3 C4 -1.3(6) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 C6 0.2(6) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C2 C1 C6 C5 -1.9(5) . . . . ?
N1 C1 C6 C5 176.2(4) . . . . ?
C12 C7 C8 C9 1.9(5) . . . . ?
N1 C7 C8 C9 -178.1(4) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C8 C9 C10 C11 -1.1(6) . . . . ?
C9 C10 C11 C12 1.8(6) . . . . ?
C10 C11 C12 C7 -0.6(6) . . . . ?
C8 C7 C12 C11 -1.2(5) . . . . ?
N1 C7 C12 C11 178.8(3) . . . . ?
C18 C13 C14 C15 1.4(6) . . . . ?
N1 C13 C14 C15 179.8(3) . . . . ?
C13 C14 C15 C16 -1.3(6) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C14 C15 C16 C22 -178.4(3) . . . . ?
C15 C16 C17 C18 0.0(5) . . . . ?
C22 C16 C17 C18 179.0(3) . . . . ?
C16 C17 C18 C13 0.2(5) . . . . ?
C14 C13 C18 C17 -0.9(5) . . . . ?
N1 C13 C18 C17 -179.3(3) . . . . ?
O1 C19 C20 C21 -176.8(3) . . . . ?
C24 C19 C20 C21 0.9(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 C23 -1.9(5) . . . . ?
C20 C21 C22 C16 178.3(3) . . . . ?
C17 C16 C22 C23 -31.1(5) . . . . ?
C15 C16 C22 C23 147.8(4) . . . . ?
C17 C16 C22 C21 148.8(3) . . . . ?
C15 C16 C22 C21 -32.3(5) . . . . ?
C21 C22 C23 C24 1.2(5) . . . . ?
C16 C22 C23 C24 -178.9(3) . . . . ?
O1 C19 C24 C23 176.1(3) . . . . ?
C20 C19 C24 C23 -1.6(5) . . . . ?
O1 C19 C24 C25 -2.8(5) . . . . ?
C20 C19 C24 C25 179.5(3) . . . . ?
C22 C23 C24 C19 0.5(5) . . . . ?
C22 C23 C24 C25 179.3(3) . . . . ?
C19 C24 C25 O2 -176.9(4) . . . . ?
C23 C24 C25 O2 4.3(6) . . . . ?
C19 C24 C25 C26 3.1(5) . . . . ?
C23 C24 C25 C26 -175.7(3) . . . . ?
O2 C25 C26 C27 178.8(4) . . . . ?
C24 C25 C26 C27 -1.2(6) . . . . ?
C25 C26 C27 O1 -1.4(7) . . . . ?
C8 C7 N1 C1 37.0(5) . . . . ?
C12 C7 N1 C1 -143.0(4) . . . . ?
C8 C7 N1 C13 -167.7(3) . . . . ?
C12 C7 N1 C13 12.3(5) . . . . ?
C2 C1 N1 C7 -144.3(3) . . . . ?
C6 C1 N1 C7 37.6(5) . . . . ?
C2 C1 N1 C13 59.7(5) . . . . ?
C6 C1 N1 C13 -118.4(3) . . . . ?
C14 C13 N1 C7 68.8(4) . . . . ?
C18 C13 N1 C7 -112.8(4) . . . . ?
C14 C13 N1 C1 -135.0(4) . . . . ?
C18 C13 N1 C1 43.4(5) . . . . ?
C26 C27 O1 C19 1.9(6) . . . . ?
C20 C19 O1 C27 178.0(3) . . . . ?
C24 C19 O1 C27 0.3(5) . . . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.080



