# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_2020052604_a
_audit_block_doi                 10.5517/ccdc.csd.cc270d9z
_database_code_depnum_ccdc_archive 'CCDC 2055960'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1007/s00706-021-02846-z 2021
loop_
_audit_author_name
_audit_author_address
'Dong-En Wu'
;Changzhou Vocational Institute of Engineering
China
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2023-06-07 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         'C29 H20 N2 O'
_chemical_formula_sum            'C29 H20 N2 O'
_chemical_formula_weight         412.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.1510(3)
_cell_length_b                   32.660(2)
_cell_length_c                   15.7551(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.710(3)
_cell_angle_gamma                90
_cell_volume                     2131.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5319
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.06

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6546
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source.type              microfocus
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15413
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.275
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4884
_reflns_number_gt                2946
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0582P)²+0.6032P] 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         4884
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1450
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.9343(4) 0.25078(5) 0.37443(11) 0.0416(4) Uani 1 1 d . . . . .
C2 C 0.7564(4) 0.22139(5) 0.33001(11) 0.0437(4) Uani 1 1 d . . . . .
H2 H 0.659513 0.227826 0.276799 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7172(4) 0.18177(5) 0.36311(11) 0.0400(4) Uani 1 1 d . . . . .
C4 C 0.5269(5) 0.15162(6) 0.31875(12) 0.0487(5) Uani 1 1 d . . . . .
H4 H 0.423696 0.157905 0.266209 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4941(5) 0.11383(6) 0.35215(13) 0.0511(5) Uani 1 1 d . . . . .
H5 H 0.368281 0.094373 0.322370 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6485(5) 0.10363(6) 0.43163(12) 0.0486(5) Uani 1 1 d . . . . .
C7 C 0.8306(5) 0.13179(5) 0.47692(12) 0.0474(5) Uani 1 1 d . . . . .
H7 H 0.929784 0.124887 0.529596 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8681(4) 0.17165(5) 0.44341(11) 0.0409(4) Uani 1 1 d . . . . .
C9 C 1.0540(5) 0.20217(5) 0.48779(11) 0.0451(5) Uani 1 1 d . . . . .
H9 H 1.157511 0.195954 0.540327 0.054 Uiso 1 1 calc R U . . .
C10 C 1.0837(5) 0.24031(5) 0.45500(11) 0.0451(5) Uani 1 1 d . . . . .
H10 H 1.204152 0.259910 0.485883 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7603(6) 0.05117(6) 0.53451(15) 0.0705(7) Uani 1 1 d . . . . .
H11A H 0.988605 0.054646 0.530869 0.106 Uiso 1 1 calc R U . . .
H11B H 0.713560 0.022810 0.543957 0.106 Uiso 1 1 calc R U . . .
H11C H 0.689391 0.067202 0.580854 0.106 Uiso 1 1 calc R U . . .
C12 C 0.9702(5) 0.29213(5) 0.33823(11) 0.0447(5) Uani 1 1 d . . . . .
C13 C 0.9308(5) 0.32833(6) 0.38954(12) 0.0508(5) Uani 1 1 d . . . . .
H13 H 1.003627 0.352986 0.368328 0.061 Uiso 1 1 calc R U . . .
C14 C 0.7988(5) 0.32948(5) 0.46478(12) 0.0453(5) Uani 1 1 d . . . . .
H14 H 0.735950 0.304594 0.487175 0.054 Uiso 1 1 calc R U . . .
C15 C 0.7444(4) 0.36593(5) 0.51486(11) 0.0417(4) Uani 1 1 d . . . . .
C16 C 0.5817(5) 0.36280(5) 0.58879(12) 0.0511(5) Uani 1 1 d . . . . .
H16 H 0.513454 0.337194 0.606208 0.061 Uiso 1 1 calc R U . . .
C17 C 0.5191(5) 0.39662(5) 0.63687(12) 0.0531(5) Uani 1 1 d . . . . .
H17 H 0.408067 0.393274 0.685808 0.064 Uiso 1 1 calc R U . . .
C18 C 0.6162(4) 0.43559(5) 0.61475(11) 0.0401(4) Uani 1 1 d . . . . .
C19 C 0.5414(4) 0.47241(5) 0.66530(11) 0.0427(4) Uani 1 1 d . . . . .
C20 C 0.3890(6) 0.46914(6) 0.74026(14) 0.0622(6) Uani 1 1 d . . . . .
H20 H 0.334842 0.443331 0.759828 0.075 Uiso 1 1 calc R U . . .
C21 C 0.3151(7) 0.50320(7) 0.78685(16) 0.0754(7) Uani 1 1 d . . . . .
H21 H 0.211459 0.500049 0.837033 0.090 Uiso 1 1 calc R U . . .
C22 C 0.3923(6) 0.54153(7) 0.76012(15) 0.0670(6) Uani 1 1 d . . . . .
H22 H 0.341104 0.564506 0.791404 0.080 Uiso 1 1 calc R U . . .
C23 C 0.5452(7) 0.54542(7) 0.68709(16) 0.0784(8) Uani 1 1 d . . . . .
H23 H 0.602123 0.571311 0.668592 0.094 Uiso 1 1 calc R U . . .
C24 C 0.6174(7) 0.51141(6) 0.63980(15) 0.0712(7) Uani 1 1 d . . . . .
H24 H 0.719875 0.514909 0.589527 0.085 Uiso 1 1 calc R U . . .
C25 C 0.7839(5) 0.43839(6) 0.54172(13) 0.0573(6) Uani 1 1 d . . . . .
H25 H 0.856294 0.463905 0.524953 0.069 Uiso 1 1 calc R U . . .
C26 C 0.8466(6) 0.40481(6) 0.49343(13) 0.0612(6) Uani 1 1 d . . . . .
H26 H 0.960652 0.408156 0.445001 0.073 Uiso 1 1 calc R U . . .
C27 C 1.0355(5) 0.29707(5) 0.25443(12) 0.0509(5) Uani 1 1 d . . . . .
C28 C 1.0976(5) 0.26440(6) 0.19729(12) 0.0518(5) Uani 1 1 d . . . . .
C29 C 1.0500(7) 0.33679(7) 0.21638(14) 0.0735(7) Uani 1 1 d . . . . .
N1 N 1.1534(5) 0.24010(6) 0.14855(11) 0.0729(6) Uani 1 1 d . . . . .
N2 N 1.0607(8) 0.36807(7) 0.18476(15) 0.1179(11) Uani 1 1 d . . . . .
O1 O 0.5960(4) 0.06431(4) 0.45718(9) 0.0629(4) 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 1.375(2) . ?
C1 C10 1.418(3) . ?
C1 C12 1.477(2) . ?
C2 C3 1.409(2) . ?
C2 H2 0.9300 . ?
C3 C8 1.414(3) . ?
C3 C4 1.418(3) . ?
C4 C5 1.352(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.363(3) . ?
C6 O1 1.367(2) . ?
C7 C8 1.417(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(2) . ?
C9 C10 1.357(2) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.423(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C27 1.375(3) . ?
C12 C13 1.447(2) . ?
C13 C14 1.338(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.454(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(2) . ?
C15 C26 1.387(2) . ?
C16 C17 1.374(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9300 . ?
C18 C25 1.386(3) . ?
C18 C19 1.486(2) . ?
C19 C20 1.380(3) . ?
C19 C24 1.378(3) . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.355(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.381(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.369(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C29 1.432(3) . ?
C27 C28 1.430(3) . ?
C28 N1 1.138(2) . ?
C29 N2 1.139(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 118.47(16) . . ?
C2 C1 C12 120.40(17) . . ?
C10 C1 C12 121.12(16) . . ?
C1 C2 C3 121.61(17) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C8 119.40(16) . . ?
C2 C3 C4 121.96(17) . . ?
C8 C3 C4 118.63(17) . . ?
C5 C4 C3 120.59(19) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.67(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 O1 124.98(18) . . ?
C7 C6 C5 120.71(18) . . ?
O1 C6 C5 114.31(17) . . ?
C6 C7 C8 119.71(18) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C3 119.67(17) . . ?
C7 C8 C9 122.13(17) . . ?
C3 C8 C9 118.20(16) . . ?
C10 C9 C8 121.18(17) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C1 121.12(17) . . ?
C9 C10 H10 119.4 . . ?
C1 C10 H10 119.4 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C27 C12 C13 118.50(16) . . ?
C27 C12 C1 120.61(16) . . ?
C13 C12 C1 120.88(15) . . ?
C14 C13 C12 125.82(17) . . ?
C14 C13 H13 117.1 . . ?
C12 C13 H13 117.1 . . ?
C13 C14 C15 126.19(17) . . ?
C13 C14 H14 116.9 . . ?
C15 C14 H14 116.9 . . ?
C16 C15 C26 116.42(16) . . ?
C16 C15 C14 119.75(16) . . ?
C26 C15 C14 123.83(16) . . ?
C17 C16 C15 121.55(17) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C18 122.09(17) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C25 C18 C17 116.03(16) . . ?
C25 C18 C19 121.69(16) . . ?
C17 C18 C19 122.27(16) . . ?
C20 C19 C24 116.58(17) . . ?
C20 C19 C18 121.29(16) . . ?
C24 C19 C18 122.13(17) . . ?
C21 C20 C19 121.6(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.7(2) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C24 120.8(2) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C23 C24 C19 121.6(2) . . ?
C23 C24 H24 119.2 . . ?
C19 C24 H24 119.2 . . ?
C26 C25 C18 122.17(17) . . ?
C26 C25 H25 118.9 . . ?
C18 C25 H25 118.9 . . ?
C25 C26 C15 121.72(18) . . ?
C25 C26 H26 119.1 . . ?
C15 C26 H26 119.1 . . ?
C12 C27 C29 121.64(17) . . ?
C12 C27 C28 124.89(17) . . ?
C29 C27 C28 113.46(16) . . ?
N1 C28 C27 175.9(2) . . ?
N2 C29 C27 178.8(2) . . ?
C6 O1 C11 117.29(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 0.8(3) . . . . ?
C12 C1 C2 C3 -179.78(16) . . . . ?
C1 C2 C3 C8 -1.0(3) . . . . ?
C1 C2 C3 C4 178.24(17) . . . . ?
C2 C3 C4 C5 179.95(17) . . . . ?
C8 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C4 C5 C6 O1 -179.52(17) . . . . ?
O1 C6 C7 C8 179.73(17) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C3 -0.2(3) . . . . ?
C6 C7 C8 C9 179.86(17) . . . . ?
C2 C3 C8 C7 -179.78(16) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
C2 C3 C8 C9 0.1(2) . . . . ?
C4 C3 C8 C9 -179.10(16) . . . . ?
C7 C8 C9 C10 -179.21(17) . . . . ?
C3 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 C1 -1.1(3) . . . . ?
C2 C1 C10 C9 0.3(3) . . . . ?
C12 C1 C10 C9 -179.18(17) . . . . ?
C2 C1 C12 C27 -44.2(3) . . . . ?
C10 C1 C12 C27 135.2(2) . . . . ?
C2 C1 C12 C13 134.47(19) . . . . ?
C10 C1 C12 C13 -46.1(3) . . . . ?
C27 C12 C13 C14 164.3(2) . . . . ?
C1 C12 C13 C14 -14.4(3) . . . . ?
C12 C13 C14 C15 -176.90(19) . . . . ?
C13 C14 C15 C16 175.0(2) . . . . ?
C13 C14 C15 C26 -5.1(3) . . . . ?
C26 C15 C16 C17 1.5(3) . . . . ?
C14 C15 C16 C17 -178.5(2) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 C25 -0.8(3) . . . . ?
C16 C17 C18 C19 178.34(19) . . . . ?
C25 C18 C19 C20 -176.6(2) . . . . ?
C17 C18 C19 C20 4.3(3) . . . . ?
C25 C18 C19 C24 3.9(3) . . . . ?
C17 C18 C19 C24 -175.1(2) . . . . ?
C24 C19 C20 C21 0.4(4) . . . . ?
C18 C19 C20 C21 -179.1(2) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 C23 -0.4(4) . . . . ?
C21 C22 C23 C24 1.0(4) . . . . ?
C22 C23 C24 C19 -0.8(4) . . . . ?
C20 C19 C24 C23 0.2(4) . . . . ?
C18 C19 C24 C23 179.7(2) . . . . ?
C17 C18 C25 C26 0.9(3) . . . . ?
C19 C18 C25 C26 -178.2(2) . . . . ?
C18 C25 C26 C15 0.2(4) . . . . ?
C16 C15 C26 C25 -1.4(3) . . . . ?
C14 C15 C26 C25 178.6(2) . . . . ?
C13 C12 C27 C29 -3.0(3) . . . . ?
C1 C12 C27 C29 175.7(2) . . . . ?
C13 C12 C27 C28 176.5(2) . . . . ?
C1 C12 C27 C28 -4.8(3) . . . . ?
C7 C6 O1 C11 -4.0(3) . . . . ?
C5 C6 O1 C11 176.37(18) . . . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_2020040503_a
_audit_block_doi                 10.5517/ccdc.csd.cc2dy8wj
_database_code_depnum_ccdc_archive 'CCDC 2232678'
loop_
_audit_author_name
_audit_author_address
MNM
;Changzhou Vocational Institute of Engineering
China
;
_audit_update_record             
;
2022-12-24 deposited with the CCDC.	2023-06-07 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         'C16 H12 N2 O'
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.021(6)
_cell_length_b                   7.962(4)
_cell_length_c                   15.851(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.442(17)
_cell_angle_gamma                90
_cell_volume                     1352.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4636
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.88

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6759
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source.type              microfocus
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13108
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.554
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3095
_reflns_number_gt                1928
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²+0.1169P] 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         3095
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1379
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 0.27706(14) 0.44340(18) 0.71453(10) 0.0485(4) Uani 1 1 d . . . . .
C2 C 0.32825(15) 0.41323(19) 0.80374(10) 0.0525(4) Uani 1 1 d . . . . .
H2 H 0.277346 0.372558 0.838411 0.063 Uiso 1 1 calc R U . . .
C3 C 0.45088(15) 0.44301(19) 0.83930(10) 0.0525(4) Uani 1 1 d . . . . .
H3 H 0.482700 0.419573 0.897742 0.063 Uiso 1 1 calc R U . . .
C4 C 0.53156(14) 0.50878(17) 0.78975(9) 0.0464(4) Uani 1 1 d . . . . .
C5 C 0.65823(14) 0.54696(19) 0.82689(10) 0.0522(4) Uani 1 1 d . . . . .
H5 H 0.691523 0.525968 0.885414 0.063 Uiso 1 1 calc R U . . .
C6 C 0.73155(15) 0.6144(2) 0.77714(11) 0.0548(4) Uani 1 1 d . . . . .
C7 C 0.68308(16) 0.6434(2) 0.68814(11) 0.0616(5) Uani 1 1 d . . . . .
H7 H 0.734375 0.687137 0.654517 0.074 Uiso 1 1 calc R U . . .
C8 C 0.56195(15) 0.6080(2) 0.65098(10) 0.0571(4) Uani 1 1 d . . . . .
H8 H 0.531147 0.628365 0.592110 0.069 Uiso 1 1 calc R U . . .
C9 C 0.48146(14) 0.54046(18) 0.70058(10) 0.0478(4) Uani 1 1 d . . . . .
C10 C 0.35448(13) 0.50619(19) 0.66481(9) 0.0499(4) Uani 1 1 d . . . . .
H10 H 0.321833 0.526375 0.606129 0.060 Uiso 1 1 calc R U . . .
C11 C 0.14397(14) 0.41471(18) 0.67577(11) 0.0519(4) Uani 1 1 d . . . . .
C12 C 0.05019(16) 0.4748(2) 0.72431(13) 0.0718(5) Uani 1 1 d . . . . .
H12A H -0.032090 0.442865 0.693287 0.108 Uiso 1 1 calc R U . . .
H12B H 0.054790 0.594917 0.729601 0.108 Uiso 1 1 calc R U . . .
H12C H 0.067972 0.425168 0.781039 0.108 Uiso 1 1 calc R U . . .
C13 C 0.90634(18) 0.6411(3) 0.89685(14) 0.0885(7) Uani 1 1 d . . . . .
H13A H 0.857031 0.702450 0.928968 0.133 Uiso 1 1 calc R U . . .
H13B H 0.989933 0.684395 0.910176 0.133 Uiso 1 1 calc R U . . .
H13C H 0.907741 0.524486 0.912384 0.133 Uiso 1 1 calc R U . . .
C14 C 0.10606(14) 0.3389(2) 0.59748(11) 0.0551(4) Uani 1 1 d . . . . .
C15 C 0.18994(16) 0.2624(2) 0.55226(11) 0.0639(5) Uani 1 1 d . . . . .
C16 C -0.02341(18) 0.3248(2) 0.55335(12) 0.0666(5) Uani 1 1 d . . . . .
N1 N 0.25346(17) 0.1952(3) 0.51534(12) 0.0916(6) Uani 1 1 d . . . . .
N2 N -0.12566(16) 0.3152(2) 0.51605(12) 0.0909(6) Uani 1 1 d . . . . .
O1 O 0.85370(10) 0.65889(17) 0.80690(8) 0.0728(4) 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 C10 1.383(2) . ?
C1 C2 1.416(2) . ?
C1 C11 1.470(2) . ?
C2 C3 1.359(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(2) . ?
C3 H3 0.9300 . ?
C4 C9 1.416(2) . ?
C4 C5 1.416(2) . ?
C5 C6 1.363(2) . ?
C5 H5 0.9300 . ?
C6 O1 1.366(2) . ?
C6 C7 1.407(2) . ?
C7 C8 1.358(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.421(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(2) . ?
C10 H10 0.9300 . ?
C11 C14 1.356(2) . ?
C11 C12 1.503(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O1 1.416(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.431(3) . ?
C14 C16 1.440(2) . ?
C15 N1 1.145(2) . ?
C16 N2 1.147(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 118.37(14) . . ?
C10 C1 C11 120.38(14) . . ?
C2 C1 C11 121.21(13) . . ?
C3 C2 C1 120.77(14) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 121.77(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C9 C4 C5 119.65(14) . . ?
C9 C4 C3 118.05(14) . . ?
C5 C4 C3 122.28(14) . . ?
C6 C5 C4 120.24(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 O1 124.86(15) . . ?
C5 C6 C7 120.45(15) . . ?
O1 C6 C7 114.69(14) . . ?
C8 C7 C6 120.46(15) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.06(15) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C4 119.18(13) . . ?
C10 C9 C8 122.69(14) . . ?
C4 C9 C8 118.12(14) . . ?
C1 C10 C9 121.83(14) . . ?
C1 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C14 C11 C1 121.12(14) . . ?
C14 C11 C12 120.54(15) . . ?
C1 C11 C12 118.32(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 C15 123.40(15) . . ?
C11 C14 C16 122.61(16) . . ?
C15 C14 C16 113.97(16) . . ?
N1 C15 C14 176.9(2) . . ?
N2 C16 C14 178.02(19) . . ?
C6 O1 C13 117.52(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -0.9(2) . . . . ?
C11 C1 C2 C3 -178.80(14) . . . . ?
C1 C2 C3 C4 1.6(2) . . . . ?
C2 C3 C4 C9 -1.2(2) . . . . ?
C2 C3 C4 C5 177.28(14) . . . . ?
C9 C4 C5 C6 0.2(2) . . . . ?
C3 C4 C5 C6 -178.21(14) . . . . ?
C4 C5 C6 O1 178.57(14) . . . . ?
C4 C5 C6 C7 -1.4(2) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
O1 C6 C7 C8 -178.52(15) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C5 C4 C9 C10 -178.32(12) . . . . ?
C3 C4 C9 C10 0.2(2) . . . . ?
C5 C4 C9 C8 0.9(2) . . . . ?
C3 C4 C9 C8 179.37(13) . . . . ?
C7 C8 C9 C10 178.32(15) . . . . ?
C7 C8 C9 C4 -0.8(2) . . . . ?
C2 C1 C10 C9 -0.1(2) . . . . ?
C11 C1 C10 C9 177.83(13) . . . . ?
C4 C9 C10 C1 0.4(2) . . . . ?
C8 C9 C10 C1 -178.75(14) . . . . ?
C10 C1 C11 C14 45.0(2) . . . . ?
C2 C1 C11 C14 -137.20(16) . . . . ?
C10 C1 C11 C12 -133.79(16) . . . . ?
C2 C1 C11 C12 44.0(2) . . . . ?
C1 C11 C14 C15 8.3(2) . . . . ?
C12 C11 C14 C15 -172.92(15) . . . . ?
C1 C11 C14 C16 -173.18(14) . . . . ?
C12 C11 C14 C16 5.6(2) . . . . ?
C5 C6 O1 C13 -3.2(3) . . . . ?
C7 C6 O1 C13 176.76(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C5 H5 N1 0.93 2.67 3.505(3) 149.0 4_666 yes

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_2021102512_a
_audit_block_doi                 10.5517/ccdc.csd.cc2dy8xk
_database_code_depnum_ccdc_archive 'CCDC 2232679'
loop_
_audit_author_name
_audit_author_address
m-BMNM
;Changzhou Vocational Institute of Engineering
China
;
_audit_update_record             
;
2022-12-24 deposited with the CCDC.	2023-06-07 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         'C29 H20 N2 O'
_chemical_formula_sum            'C29 H20 N2 O'
_chemical_formula_weight         412.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   25.2179(13)
_cell_length_b                   11.4889(6)
_cell_length_c                   7.5967(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.619(2)
_cell_angle_gamma                90
_cell_volume                     2190.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5147
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.56

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6850
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            21542
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4947
_reflns_number_gt                2565
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0510P)²+0.4260P] 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         4947
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1549
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.73924(7) 0.49807(17) 0.7526(3) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.77510(7) 0.59015(18) 0.8167(3) 0.0480(5) Uani 1 1 d . . . . .
H2 H 0.806308 0.570080 0.885415 0.058 Uiso 1 1 calc R U . . .
C3 C 0.76568(8) 0.70260(18) 0.7821(3) 0.0488(5) Uani 1 1 d . . . . .
H3 H 0.733568 0.719133 0.715911 0.059 Uiso 1 1 calc R U . . .
C4 C 0.79878(7) 0.80239(17) 0.8338(3) 0.0444(5) Uani 1 1 d . . . . .
C5 C 0.84865(7) 0.79445(18) 0.9299(3) 0.0460(5) Uani 1 1 d . . . . .
H5 H 0.862287 0.721362 0.961510 0.055 Uiso 1 1 calc R U . . .
C6 C 0.87852(7) 0.89263(17) 0.9798(3) 0.0453(5) Uani 1 1 d . . . . .
C7 C 0.93245(8) 0.88371(17) 1.0757(3) 0.0466(5) Uani 1 1 d . . . . .
C8 C 0.96583(8) 0.79127(19) 1.0465(3) 0.0543(6) Uani 1 1 d . . . . .
H8 H 0.953665 0.732143 0.969234 0.065 Uiso 1 1 calc R U . . .
C9 C 1.01673(8) 0.7857(2) 1.1302(3) 0.0623(6) Uani 1 1 d . . . . .
H9 H 1.038483 0.722826 1.109244 0.075 Uiso 1 1 calc R U . . .
C10 C 1.03557(9) 0.8719(2) 1.2441(3) 0.0644(7) Uani 1 1 d . . . . .
H10 H 1.069714 0.867186 1.302226 0.077 Uiso 1 1 calc R U . . .
C11 C 1.00373(10) 0.9646(2) 1.2712(3) 0.0690(7) Uani 1 1 d . . . . .
H11 H 1.016685 1.024639 1.345537 0.083 Uiso 1 1 calc R U . . .
C12 C 0.95252(9) 0.97043(19) 1.1898(3) 0.0617(6) Uani 1 1 d . . . . .
H12 H 0.931111 1.033644 1.211869 0.074 Uiso 1 1 calc R U . . .
C13 C 0.85661(8) 1.00106(18) 0.9311(3) 0.0568(6) Uani 1 1 d . . . . .
H13 H 0.875429 1.068339 0.964996 0.068 Uiso 1 1 calc R U . . .
C14 C 0.80812(9) 1.01023(19) 0.8348(3) 0.0613(7) Uani 1 1 d . . . . .
H14 H 0.794555 1.083334 0.802901 0.074 Uiso 1 1 calc R U . . .
C15 C 0.77940(8) 0.91279(19) 0.7851(3) 0.0533(6) Uani 1 1 d . . . . .
H15 H 0.746659 0.920083 0.718200 0.064 Uiso 1 1 calc R U . . .
C16 C 0.68503(7) 0.52946(16) 0.6736(3) 0.0429(5) Uani 1 1 d . . . . .
C17 C 0.66893(7) 0.50313(16) 0.5018(3) 0.0443(5) Uani 1 1 d . . . . .
H17 H 0.691521 0.460823 0.436148 0.053 Uiso 1 1 calc R U . . .
C18 C 0.61850(7) 0.53882(16) 0.4208(3) 0.0409(5) Uani 1 1 d . . . . .
C19 C 0.60241(7) 0.51687(18) 0.2417(3) 0.0505(6) Uani 1 1 d . . . . .
H19 H 0.625092 0.477377 0.172914 0.061 Uiso 1 1 calc R U . . .
C20 C 0.55401(8) 0.55287(18) 0.1685(3) 0.0521(6) Uani 1 1 d . . . . .
H20 H 0.544135 0.538797 0.049204 0.063 Uiso 1 1 calc R U . . .
C21 C 0.51856(7) 0.61100(17) 0.2694(3) 0.0444(5) Uani 1 1 d . . . . .
C22 C 0.53255(7) 0.63485(16) 0.4427(3) 0.0461(5) Uani 1 1 d . . . . .
H22 H 0.509028 0.673951 0.508881 0.055 Uiso 1 1 calc R U . . .
C23 C 0.58360(7) 0.59955(16) 0.5227(3) 0.0403(5) Uani 1 1 d . . . . .
C24 C 0.60060(8) 0.62361(18) 0.7009(3) 0.0519(6) Uani 1 1 d . . . . .
H24 H 0.577831 0.662543 0.770042 0.062 Uiso 1 1 calc R U . . .
C25 C 0.64978(7) 0.59092(19) 0.7737(3) 0.0524(6) Uani 1 1 d . . . . .
H25 H 0.660374 0.609262 0.891177 0.063 Uiso 1 1 calc R U . . .
C26 C 0.43190(8) 0.6983(2) 0.2681(3) 0.0653(7) Uani 1 1 d . . . . .
H26A H 0.423162 0.650455 0.364710 0.098 Uiso 1 1 calc R U . . .
H26B H 0.400507 0.711130 0.188340 0.098 Uiso 1 1 calc R U . . .
H26C H 0.445529 0.771708 0.312835 0.098 Uiso 1 1 calc R U . . .
C27 C 0.75508(7) 0.38468(17) 0.7613(3) 0.0484(5) Uani 1 1 d . . . . .
C28 C 0.80719(9) 0.35106(19) 0.8360(3) 0.0618(6) Uani 1 1 d . . . . .
C29 C 0.72157(8) 0.2901(2) 0.6978(3) 0.0540(6) Uani 1 1 d . . . . .
N1 N 0.84819(9) 0.3239(2) 0.8964(4) 0.0972(8) Uani 1 1 d . . . . .
N2 N 0.69682(8) 0.21148(18) 0.6477(3) 0.0737(6) Uani 1 1 d . . . . .
O1 O 0.47118(5) 0.64156(13) 0.17678(19) 0.0585(4) 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 C27 1.362(3) . ?
C1 C2 1.445(3) . ?
C1 C16 1.483(3) . ?
C2 C3 1.335(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.449(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 C15 1.396(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C13 1.398(3) . ?
C6 C7 1.482(3) . ?
C7 C12 1.384(3) . ?
C7 C8 1.386(3) . ?
C8 C9 1.377(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.362(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.363(3) . ?
C16 C25 1.414(3) . ?
C17 C18 1.418(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.404(3) . ?
C18 C23 1.412(3) . ?
C19 C20 1.355(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.357(3) . ?
C21 O1 1.372(2) . ?
C22 C23 1.428(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.407(3) . ?
C24 C25 1.361(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 O1 1.422(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C29 1.431(3) . ?
C27 C28 1.432(3) . ?
C28 N1 1.133(3) . ?
C29 N2 1.142(3) . ?

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
C27 C1 C2 120.86(17) . . ?
C27 C1 C16 120.44(17) . . ?
C2 C1 C16 118.69(17) . . ?
C3 C2 C1 123.29(18) . . ?
C3 C2 H2 118.4 . . ?
C1 C2 H2 118.4 . . ?
C2 C3 C4 128.72(19) . . ?
C2 C3 H3 115.6 . . ?
C4 C3 H3 115.6 . . ?
C5 C4 C15 118.20(18) . . ?
C5 C4 C3 123.79(18) . . ?
C15 C4 C3 118.01(18) . . ?
C6 C5 C4 121.83(18) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C13 117.52(18) . . ?
C5 C6 C7 121.68(17) . . ?
C13 C6 C7 120.77(18) . . ?
C12 C7 C8 117.47(19) . . ?
C12 C7 C6 121.33(19) . . ?
C8 C7 C6 121.11(18) . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C14 C13 C6 121.3(2) . . ?
C14 C13 H13 119.3 . . ?
C6 C13 H13 119.3 . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C4 120.59(19) . . ?
C14 C15 H15 119.7 . . ?
C4 C15 H15 119.7 . . ?
C17 C16 C25 118.83(17) . . ?
C17 C16 C1 120.68(18) . . ?
C25 C16 C1 120.45(19) . . ?
C16 C17 C18 121.46(18) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C23 118.91(17) . . ?
C19 C18 C17 122.03(18) . . ?
C23 C18 C17 119.05(19) . . ?
C20 C19 C18 120.41(19) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 121.1(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 O1 125.22(18) . . ?
C22 C21 C20 120.50(18) . . ?
O1 C21 C20 114.27(18) . . ?
C21 C22 C23 119.58(18) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C18 118.49(17) . . ?
C24 C23 C22 122.08(18) . . ?
C18 C23 C22 119.43(18) . . ?
C25 C24 C23 121.13(19) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C24 C25 C16 121.0(2) . . ?
C24 C25 H25 119.5 . . ?
C16 C25 H25 119.5 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 C27 C29 123.31(18) . . ?
C1 C27 C28 122.03(18) . . ?
C29 C27 C28 114.66(18) . . ?
N1 C28 C27 179.3(3) . . ?
N2 C29 C27 176.9(2) . . ?
C21 O1 C26 118.71(16) . . ?

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
C27 C1 C2 C3 167.0(2) . . . . ?
C16 C1 C2 C3 -11.8(3) . . . . ?
C1 C2 C3 C4 -178.15(19) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C2 C3 C4 C15 -178.3(2) . . . . ?
C15 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C6 -178.62(18) . . . . ?
C4 C5 C6 C13 0.5(3) . . . . ?
C4 C5 C6 C7 -177.49(18) . . . . ?
C5 C6 C7 C12 -151.4(2) . . . . ?
C13 C6 C7 C12 30.7(3) . . . . ?
C5 C6 C7 C8 32.3(3) . . . . ?
C13 C6 C7 C8 -145.5(2) . . . . ?
C12 C7 C8 C9 0.9(3) . . . . ?
C6 C7 C8 C9 177.26(19) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C9 C10 C11 C12 2.0(4) . . . . ?
C10 C11 C12 C7 -1.3(4) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C6 C7 C12 C11 -176.5(2) . . . . ?
C5 C6 C13 C14 -1.4(3) . . . . ?
C7 C6 C13 C14 176.6(2) . . . . ?
C6 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C4 0.9(3) . . . . ?
C5 C4 C15 C14 -1.7(3) . . . . ?
C3 C4 C15 C14 177.97(19) . . . . ?
C27 C1 C16 C17 -60.4(3) . . . . ?
C2 C1 C16 C17 118.3(2) . . . . ?
C27 C1 C16 C25 121.8(2) . . . . ?
C2 C1 C16 C25 -59.4(3) . . . . ?
C25 C16 C17 C18 1.8(3) . . . . ?
C1 C16 C17 C18 -176.01(16) . . . . ?
C16 C17 C18 C19 177.06(18) . . . . ?
C16 C17 C18 C23 -2.2(3) . . . . ?
C23 C18 C19 C20 -0.4(3) . . . . ?
C17 C18 C19 C20 -179.62(18) . . . . ?
C18 C19 C20 C21 -1.0(3) . . . . ?
C19 C20 C21 C22 1.5(3) . . . . ?
C19 C20 C21 O1 -179.82(18) . . . . ?
O1 C21 C22 C23 -179.04(17) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C19 C18 C23 C24 -178.48(18) . . . . ?
C17 C18 C23 C24 0.8(3) . . . . ?
C19 C18 C23 C22 1.3(3) . . . . ?
C17 C18 C23 C22 -179.41(16) . . . . ?
C21 C22 C23 C24 178.92(19) . . . . ?
C21 C22 C23 C18 -0.9(3) . . . . ?
C18 C23 C24 C25 0.9(3) . . . . ?
C22 C23 C24 C25 -178.87(19) . . . . ?
C23 C24 C25 C16 -1.3(3) . . . . ?
C17 C16 C25 C24 0.0(3) . . . . ?
C1 C16 C25 C24 177.78(18) . . . . ?
C2 C1 C27 C29 -179.13(19) . . . . ?
C16 C1 C27 C29 -0.4(3) . . . . ?
C2 C1 C27 C28 1.0(3) . . . . ?
C16 C1 C27 C28 179.74(19) . . . . ?
C22 C21 O1 C26 -3.0(3) . . . . ?
C20 C21 O1 C26 178.44(17) . . . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_2021102510_a
_audit_block_doi                 10.5517/ccdc.csd.cc2dy90p
_database_code_depnum_ccdc_archive 'CCDC 2232682'
loop_
_audit_author_name
_audit_author_address
'You Wu'
;Changzhou Vocational Institute of Engineering
China
;
_audit_update_record             
;
2022-12-24 deposited with the CCDC.	2023-06-07 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         'C29 H20 N2 O'
_chemical_formula_sum            'C29 H20 N2 O'
_chemical_formula_weight         412.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6109(5)
_cell_length_b                   10.0070(4)
_cell_length_c                   23.2959(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.533(2)
_cell_angle_gamma                90
_cell_volume                     2239.71(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4728
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      26.60

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6589
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            17698
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5072
_reflns_number_gt                2594
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0597P)²+0.3787P] 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       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5072
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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 0.6222(2) 0.45785(19) 0.59486(8) 0.0534(5) Uani 1 1 d . . . . .
C2 C 0.5593(2) 0.3288(2) 0.58260(9) 0.0620(6) Uani 1 1 d . . . . .
H2 H 0.586565 0.285429 0.549426 0.074 Uiso 1 1 calc R U . . .
C3 C 0.4665(2) 0.26687(19) 0.61437(9) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.444232 0.306180 0.649116 0.067 Uiso 1 1 calc R U . . .
C4 C 0.3962(2) 0.1412(2) 0.59891(9) 0.0631(6) Uani 1 1 d . . . . .
C5 C 0.3694(3) 0.1120(2) 0.54107(11) 0.0948(9) Uani 1 1 d . . . . .
H5 H 0.403569 0.168740 0.513138 0.114 Uiso 1 1 calc R U . . .
C6 C 0.2936(4) 0.0013(3) 0.52438(14) 0.1179(11) Uani 1 1 d . . . . .
H6 H 0.277181 -0.016787 0.485625 0.141 Uiso 1 1 calc R U . . .
C7 C 0.2424(4) -0.0823(3) 0.56554(17) 0.1178(12) Uani 1 1 d . . . . .
H7 H 0.189300 -0.156203 0.554686 0.141 Uiso 1 1 calc R U . . .
C8 C 0.2694(3) -0.0570(2) 0.62259(13) 0.0905(8) Uani 1 1 d . . . . .
H8 H 0.235652 -0.115726 0.649861 0.109 Uiso 1 1 calc R U . . .
C9 C 0.3455(2) 0.05354(19) 0.64080(10) 0.0648(6) Uani 1 1 d . . . . .
C10 C 0.3734(2) 0.07349(19) 0.70294(10) 0.0583(6) Uani 1 1 d . . . . .
C11 C 0.2682(3) 0.0538(3) 0.74205(14) 0.0875(8) Uani 1 1 d . . . . .
H11 H 0.180003 0.028338 0.728823 0.105 Uiso 1 1 calc R U . . .
C12 C 0.2931(3) 0.0714(3) 0.79996(14) 0.1010(10) Uani 1 1 d . . . . .
H12 H 0.221388 0.058117 0.825388 0.121 Uiso 1 1 calc R U . . .
C13 C 0.4215(3) 0.1080(2) 0.82051(11) 0.0846(8) Uani 1 1 d . . . . .
H13 H 0.436809 0.122145 0.859620 0.102 Uiso 1 1 calc R U . . .
C14 C 0.5274(3) 0.1238(2) 0.78328(10) 0.0664(6) Uani 1 1 d . . . . .
H14 H 0.615915 0.146453 0.797196 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5038(2) 0.10627(18) 0.72485(9) 0.0572(5) Uani 1 1 d . . . . .
H15 H 0.577061 0.116757 0.699958 0.069 Uiso 1 1 calc R U . . .
C16 C 0.6046(2) 0.52523(18) 0.65093(8) 0.0501(5) Uani 1 1 d . . . . .
C17 C 0.5577(2) 0.65974(19) 0.65248(9) 0.0586(5) Uani 1 1 d . . . . .
H17 H 0.536541 0.704119 0.618269 0.070 Uiso 1 1 calc R U . . .
C18 C 0.5432(2) 0.72454(19) 0.70328(9) 0.0596(6) Uani 1 1 d . . . . .
H18 H 0.511948 0.812500 0.703169 0.072 Uiso 1 1 calc R U . . .
C19 C 0.57431(19) 0.66170(18) 0.75573(8) 0.0504(5) Uani 1 1 d . . . . .
C20 C 0.5551(2) 0.7259(2) 0.80953(9) 0.0619(6) Uani 1 1 d . . . . .
H20 H 0.523269 0.813582 0.810615 0.074 Uiso 1 1 calc R U . . .
C21 C 0.5831(2) 0.6593(2) 0.85902(9) 0.0682(6) Uani 1 1 d . . . . .
C22 C 0.6326(3) 0.5279(2) 0.85827(9) 0.0755(7) Uani 1 1 d . . . . .
H22 H 0.652660 0.483887 0.892669 0.091 Uiso 1 1 calc R U . . .
C23 C 0.6513(2) 0.4647(2) 0.80799(9) 0.0657(6) Uani 1 1 d . . . . .
H23 H 0.684455 0.377389 0.808208 0.079 Uiso 1 1 calc R U . . .
C24 C 0.62188(19) 0.52805(18) 0.75525(8) 0.0483(5) Uani 1 1 d . . . . .
C25 C 0.63528(19) 0.46296(18) 0.70173(8) 0.0513(5) Uani 1 1 d . . . . .
H25 H 0.666021 0.374855 0.701220 0.062 Uiso 1 1 calc R U . . .
C26 C 0.4841(3) 0.8215(3) 0.92006(12) 0.1089(10) Uani 1 1 d . . . . .
H26A H 0.527841 0.897033 0.902679 0.163 Uiso 1 1 calc R U . . .
H26B H 0.472561 0.838626 0.960200 0.163 Uiso 1 1 calc R U . . .
H26C H 0.394659 0.806533 0.901840 0.163 Uiso 1 1 calc R U . . .
C27 C 0.6977(2) 0.5188(2) 0.55397(8) 0.0594(6) Uani 1 1 d . . . . .
C28 C 0.7760(3) 0.6381(2) 0.56445(8) 0.0664(6) Uani 1 1 d . . . . .
C29 C 0.7110(3) 0.4660(2) 0.49719(10) 0.0720(7) Uani 1 1 d . . . . .
N1 N 0.8422(3) 0.7313(2) 0.57092(9) 0.0965(7) Uani 1 1 d . . . . .
N2 N 0.7223(3) 0.4274(2) 0.45161(10) 0.1018(8) Uani 1 1 d . . . . .
O1 O 0.5667(2) 0.70907(18) 0.91350(7) 0.0995(6) 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 C27 1.357(3) . ?
C1 C2 1.451(3) . ?
C1 C16 1.484(3) . ?
C2 C3 1.328(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.467(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(3) . ?
C4 C9 1.409(3) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.479(3) . ?
C10 C15 1.380(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.364(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C25 1.363(2) . ?
C16 C17 1.420(3) . ?
C17 C18 1.360(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.399(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.414(3) . ?
C19 C20 1.425(3) . ?
C20 C21 1.352(3) . ?
C20 H20 0.9300 . ?
C21 O1 1.376(2) . ?
C21 C22 1.399(3) . ?
C22 C23 1.348(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.405(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.416(2) . ?
C25 H25 0.9300 . ?
C26 O1 1.388(3) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.429(3) . ?
C27 C29 1.434(3) . ?
C28 N1 1.137(3) . ?
C29 N2 1.138(3) . ?

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
C27 C1 C2 119.30(18) . . ?
C27 C1 C16 119.30(17) . . ?
C2 C1 C16 121.39(18) . . ?
C3 C2 C1 126.03(19) . . ?
C3 C2 H2 117.0 . . ?
C1 C2 H2 117.0 . . ?
C2 C3 C4 125.1(2) . . ?
C2 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
C5 C4 C9 118.7(2) . . ?
C5 C4 C3 119.2(2) . . ?
C9 C4 C3 121.94(19) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C7 C6 C5 119.3(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.9(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C8 C9 C4 118.3(2) . . ?
C8 C9 C10 119.2(2) . . ?
C4 C9 C10 122.47(19) . . ?
C15 C10 C11 117.3(2) . . ?
C15 C10 C9 122.2(2) . . ?
C11 C10 C9 120.4(2) . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 121.1(2) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C25 C16 C17 118.22(17) . . ?
C25 C16 C1 121.97(17) . . ?
C17 C16 C1 119.79(16) . . ?
C18 C17 C16 120.93(18) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.41(18) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C24 118.68(17) . . ?
C18 C19 C20 122.40(18) . . ?
C24 C19 C20 118.88(17) . . ?
C21 C20 C19 120.04(19) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 O1 125.7(2) . . ?
C20 C21 C22 120.82(19) . . ?
O1 C21 C22 113.5(2) . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 121.3(2) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 118.54(17) . . ?
C23 C24 C25 122.81(17) . . ?
C19 C24 C25 118.65(16) . . ?
C16 C25 C24 122.12(17) . . ?
C16 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
O1 C26 H26A 109.5 . . ?
O1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 C27 C28 122.98(18) . . ?
C1 C27 C29 122.99(19) . . ?
C28 C27 C29 113.96(18) . . ?
N1 C28 C27 176.9(3) . . ?
N2 C29 C27 178.2(2) . . ?
C21 O1 C26 118.3(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
C27 C1 C2 C3 -169.1(2) . . . . ?
C16 C1 C2 C3 10.2(3) . . . . ?
C1 C2 C3 C4 175.02(19) . . . . ?
C2 C3 C4 C5 -31.1(3) . . . . ?
C2 C3 C4 C9 153.7(2) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C5 C6 -174.5(3) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -1.5(5) . . . . ?
C6 C7 C8 C9 1.4(5) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C5 C4 C9 C8 -0.9(3) . . . . ?
C3 C4 C9 C8 174.3(2) . . . . ?
C5 C4 C9 C10 177.6(2) . . . . ?
C3 C4 C9 C10 -7.2(3) . . . . ?
C8 C9 C10 C15 133.6(2) . . . . ?
C4 C9 C10 C15 -44.9(3) . . . . ?
C8 C9 C10 C11 -43.6(3) . . . . ?
C4 C9 C10 C11 137.9(2) . . . . ?
C15 C10 C11 C12 2.4(3) . . . . ?
C9 C10 C11 C12 179.7(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C11 C10 C15 C14 -2.4(3) . . . . ?
C9 C10 C15 C14 -179.69(18) . . . . ?
C13 C14 C15 C10 0.4(3) . . . . ?
C27 C1 C16 C25 -127.3(2) . . . . ?
C2 C1 C16 C25 53.3(3) . . . . ?
C27 C1 C16 C17 51.1(3) . . . . ?
C2 C1 C16 C17 -128.3(2) . . . . ?
C25 C16 C17 C18 -0.3(3) . . . . ?
C1 C16 C17 C18 -178.74(18) . . . . ?
C16 C17 C18 C19 0.2(3) . . . . ?
C17 C18 C19 C24 0.1(3) . . . . ?
C17 C18 C19 C20 -177.63(19) . . . . ?
C18 C19 C20 C21 178.1(2) . . . . ?
C24 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 O1 -178.9(2) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C20 C21 C22 C23 -1.0(4) . . . . ?
O1 C21 C22 C23 178.7(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C19 1.3(3) . . . . ?
C22 C23 C24 C25 -177.5(2) . . . . ?
C18 C19 C24 C23 -179.20(18) . . . . ?
C20 C19 C24 C23 -1.4(3) . . . . ?
C18 C19 C24 C25 -0.4(3) . . . . ?
C20 C19 C24 C25 177.41(17) . . . . ?
C17 C16 C25 C24 -0.1(3) . . . . ?
C1 C16 C25 C24 178.39(18) . . . . ?
C23 C24 C25 C16 179.14(19) . . . . ?
C19 C24 C25 C16 0.4(3) . . . . ?
C2 C1 C27 C28 -172.7(2) . . . . ?
C16 C1 C27 C28 7.9(3) . . . . ?
C2 C1 C27 C29 4.3(3) . . . . ?
C16 C1 C27 C29 -175.02(19) . . . . ?
C20 C21 O1 C26 17.1(4) . . . . ?
C22 C21 O1 C26 -162.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C22 H22 N1 0.93 2.67 3.401(3) 136.4 2_646 yes

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030



