# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2010048'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2021-03-03 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         'C26 H18 N2 O2'
_chemical_formula_sum            'C26 H18 N2 O2'
_chemical_formula_weight         390.42

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                   13.8506(3)
_cell_length_b                   8.2078(2)
_cell_length_c                   17.5327(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.5150(10)
_cell_angle_gamma                90
_cell_volume                     1971.20(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8223
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      68.04

_exptl_crystal_description       Prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.670
_shelx_estimated_absorpt_T_min   0.814
_shelx_estimated_absorpt_T_max   0.861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_process_details   '(SADABS; Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12562
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         65.991
_diffrn_reflns_theta_full        65.991
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3427
_reflns_number_gt                3257
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2018) and DIAMOND (Brandenburg, 2010)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, 2018) and and PLATON (Spek, 2009)
;
_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)+(0.0751P)²+0.5299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0033(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3427
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.31171(8) 0.19982(15) 0.48379(6) 0.0462(3) Uani 1 1 d . . . . .
O2 O 0.49746(8) 0.21094(14) 0.50039(6) 0.0441(3) Uani 1 1 d . . . . .
N1 N 0.19786(11) 0.0922(2) 0.54438(8) 0.0546(4) Uani 1 1 d . . . . .
H1A H 0.252703 0.049426 0.569248 0.082 Uiso 1 1 d R U . . .
H1B H 0.153559 0.013875 0.533266 0.082 Uiso 1 1 d R U . . .
N2 N -0.02592(12) 0.1075(3) 0.41836(11) 0.0707(5) Uani 1 1 d . . . . .
C1 C 0.21590(11) 0.1608(2) 0.47895(9) 0.0406(4) Uani 1 1 d . . . . .
C2 C 0.15063(12) 0.1943(2) 0.41522(9) 0.0433(4) Uani 1 1 d . . . . .
C3 C 0.17741(11) 0.2796(2) 0.34464(9) 0.0417(4) Uani 1 1 d . . . . .
H3 H 0.148658 0.388918 0.342380 0.050 Uiso 1 1 calc R U . . .
C4 C 0.28760(11) 0.29810(19) 0.35321(9) 0.0404(4) Uani 1 1 d . . . . .
C5 C 0.34554(11) 0.26518(19) 0.41931(8) 0.0388(3) Uani 1 1 d . . . . .
C6 C 0.44997(11) 0.29527(18) 0.43803(8) 0.0386(3) Uani 1 1 d . . . . .
C7 C 0.51240(11) 0.3932(2) 0.40719(9) 0.0422(4) Uani 1 1 d . . . . .
H7 H 0.497076 0.461965 0.364964 0.051 Uiso 1 1 calc R U . . .
C8 C 0.60684(11) 0.37100(19) 0.45202(9) 0.0410(4) Uani 1 1 d . . . . .
C9 C 0.70057(13) 0.4328(2) 0.45010(11) 0.0553(5) Uani 1 1 d . . . . .
H9 H 0.712383 0.508202 0.412963 0.066 Uiso 1 1 calc R U . . .
C10 C 0.77508(13) 0.3778(3) 0.50548(13) 0.0638(5) Uani 1 1 d . . . . .
H10 H 0.837992 0.417380 0.505471 0.077 Uiso 1 1 calc R U . . .
C11 C 0.75839(15) 0.2655(3) 0.56076(13) 0.0664(5) Uani 1 1 d . . . . .
H11 H 0.810392 0.231445 0.596994 0.080 Uiso 1 1 calc R U . . .
C12 C 0.66729(14) 0.2031(3) 0.56364(12) 0.0591(5) Uani 1 1 d . . . . .
H12 H 0.655828 0.127767 0.600914 0.071 Uiso 1 1 calc R U . . .
C13 C 0.59352(11) 0.2582(2) 0.50808(9) 0.0414(4) Uani 1 1 d . . . . .
C14 C 0.05304(12) 0.1467(2) 0.41628(10) 0.0493(4) Uani 1 1 d . . . . .
C15 C 0.13698(11) 0.1902(2) 0.27005(9) 0.0440(4) Uani 1 1 d . . . . .
C16 C 0.07673(14) 0.2728(3) 0.21275(11) 0.0592(5) Uani 1 1 d . . . . .
H16 H 0.061718 0.381789 0.219474 0.071 Uiso 1 1 calc R U . . .
C17 C 0.03860(16) 0.1922(3) 0.14496(12) 0.0721(6) Uani 1 1 d . . . . .
H17 H -0.001853 0.247529 0.106414 0.086 Uiso 1 1 calc R U . . .
C18 C 0.06055(16) 0.0321(3) 0.13506(12) 0.0713(6) Uani 1 1 d . . . . .
H18 H 0.034588 -0.021633 0.089947 0.086 Uiso 1 1 calc R U . . .
C19 C 0.12111(17) -0.0502(3) 0.19178(13) 0.0707(6) Uani 1 1 d . . . . .
H19 H 0.136176 -0.159118 0.184960 0.085 Uiso 1 1 calc R U . . .
C20 C 0.15929(15) 0.0299(3) 0.25876(11) 0.0591(5) Uani 1 1 d . . . . .
H20 H 0.200650 -0.025525 0.296712 0.071 Uiso 1 1 calc R U . . .
C21 C 0.32902(11) 0.3624(2) 0.28544(9) 0.0419(4) Uani 1 1 d . . . . .
C22 C 0.38384(14) 0.2634(2) 0.24411(10) 0.0522(4) Uani 1 1 d . . . . .
H22 H 0.392975 0.154292 0.257585 0.063 Uiso 1 1 calc R U . . .
C23 C 0.42512(15) 0.3257(3) 0.18289(11) 0.0599(5) Uani 1 1 d . . . . .
H23 H 0.461951 0.258540 0.155644 0.072 Uiso 1 1 calc R U . . .
C24 C 0.41173(15) 0.4864(3) 0.16245(10) 0.0601(5) Uani 1 1 d . . . . .
H24 H 0.440591 0.528910 0.122131 0.072 Uiso 1 1 calc R U . . .
C25 C 0.35564(16) 0.5839(3) 0.20171(12) 0.0633(5) Uani 1 1 d . . . . .
H25 H 0.345729 0.692368 0.187350 0.076 Uiso 1 1 calc R U . . .
C26 C 0.31352(14) 0.5224(2) 0.26260(11) 0.0539(4) Uani 1 1 d . . . . .
H26 H 0.274610 0.589234 0.288213 0.065 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3555(19) . ?
O1 C5 1.3937(18) . ?
O2 C13 1.3731(19) . ?
O2 C6 1.376(2) . ?
N1 C1 1.334(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N2 C14 1.146(2) . ?
C1 C2 1.357(2) . ?
C2 C14 1.410(2) . ?
C2 C3 1.515(2) . ?
C3 C4 1.519(2) . ?
C3 C15 1.531(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.336(2) . ?
C4 C21 1.490(2) . ?
C5 C6 1.456(2) . ?
C6 C7 1.351(2) . ?
C7 C8 1.434(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.382(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9300 . ?
C15 C20 1.373(3) . ?
C15 C16 1.384(3) . ?
C16 C17 1.394(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.380(3) . ?
C21 C22 1.387(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.372(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.385(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
C1 O1 C5 118.93(12) . . ?
C13 O2 C6 106.15(12) . . ?
C1 N1 H1A 109.4 . . ?
C1 N1 H1B 109.1 . . ?
H1A N1 H1B 109.5 . . ?
N1 C1 O1 110.62(13) . . ?
N1 C1 C2 127.34(15) . . ?
O1 C1 C2 122.02(14) . . ?
C1 C2 C14 117.13(14) . . ?
C1 C2 C3 123.52(14) . . ?
C14 C2 C3 119.34(14) . . ?
C2 C3 C4 109.23(13) . . ?
C2 C3 C15 111.93(13) . . ?
C4 C3 C15 111.55(13) . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C15 C3 H3 108.0 . . ?
C5 C4 C21 120.69(14) . . ?
C5 C4 C3 122.10(14) . . ?
C21 C4 C3 117.15(13) . . ?
C4 C5 O1 123.41(14) . . ?
C4 C5 C6 127.62(14) . . ?
O1 C5 C6 108.93(13) . . ?
C7 C6 O2 111.00(14) . . ?
C7 C6 C5 133.16(15) . . ?
O2 C6 C5 115.84(13) . . ?
C6 C7 C8 106.90(14) . . ?
C6 C7 H7 126.5 . . ?
C8 C7 H7 126.5 . . ?
C13 C8 C9 118.82(16) . . ?
C13 C8 C7 105.54(13) . . ?
C9 C8 C7 135.63(16) . . ?
C10 C9 C8 117.58(18) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
C11 C10 C9 121.68(17) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 121.75(19) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 116.19(19) . . ?
C11 C12 H12 121.9 . . ?
C13 C12 H12 121.9 . . ?
O2 C13 C12 125.62(16) . . ?
O2 C13 C8 110.41(14) . . ?
C12 C13 C8 123.98(16) . . ?
N2 C14 C2 178.91(19) . . ?
C20 C15 C16 119.27(17) . . ?
C20 C15 C3 121.38(15) . . ?
C16 C15 C3 119.36(17) . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.1(2) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.2(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 119.7(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 120.8(2) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C26 C21 C22 118.64(15) . . ?
C26 C21 C4 120.43(15) . . ?
C22 C21 C4 120.92(15) . . ?
C23 C22 C21 120.55(18) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.11(19) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.67(17) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.62(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.33(18) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 N1 176.68(14) . . . . ?
C5 O1 C1 C2 -4.9(2) . . . . ?
N1 C1 C2 C14 -2.5(3) . . . . ?
O1 C1 C2 C14 179.38(15) . . . . ?
N1 C1 C2 C3 177.19(17) . . . . ?
O1 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 7.6(2) . . . . ?
C14 C2 C3 C4 -172.66(15) . . . . ?
C1 C2 C3 C15 131.68(17) . . . . ?
C14 C2 C3 C15 -48.6(2) . . . . ?
C2 C3 C4 C5 -9.5(2) . . . . ?
C15 C3 C4 C5 -133.81(16) . . . . ?
C2 C3 C4 C21 173.22(14) . . . . ?
C15 C3 C4 C21 48.95(19) . . . . ?
C21 C4 C5 O1 -177.79(14) . . . . ?
C3 C4 C5 O1 5.1(2) . . . . ?
C21 C4 C5 C6 4.9(3) . . . . ?
C3 C4 C5 C6 -172.28(15) . . . . ?
C1 O1 C5 C4 2.8(2) . . . . ?
C1 O1 C5 C6 -179.37(13) . . . . ?
C13 O2 C6 C7 -0.37(17) . . . . ?
C13 O2 C6 C5 -179.41(12) . . . . ?
C4 C5 C6 C7 18.7(3) . . . . ?
O1 C5 C6 C7 -158.92(17) . . . . ?
C4 C5 C6 O2 -162.49(15) . . . . ?
O1 C5 C6 O2 19.84(18) . . . . ?
O2 C6 C7 C8 0.28(18) . . . . ?
C5 C6 C7 C8 179.09(16) . . . . ?
C6 C7 C8 C13 -0.07(17) . . . . ?
C6 C7 C8 C9 179.09(18) . . . . ?
C13 C8 C9 C10 -0.5(2) . . . . ?
C7 C8 C9 C10 -179.61(18) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C6 O2 C13 C12 -179.96(16) . . . . ?
C6 O2 C13 C8 0.32(17) . . . . ?
C11 C12 C13 O2 179.69(17) . . . . ?
C11 C12 C13 C8 -0.6(3) . . . . ?
C9 C8 C13 O2 -179.48(14) . . . . ?
C7 C8 C13 O2 -0.16(17) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C7 C8 C13 C12 -179.88(17) . . . . ?
C2 C3 C15 C20 -56.9(2) . . . . ?
C4 C3 C15 C20 65.8(2) . . . . ?
C2 C3 C15 C16 123.10(17) . . . . ?
C4 C3 C15 C16 -114.16(17) . . . . ?
C20 C15 C16 C17 0.8(3) . . . . ?
C3 C15 C16 C17 -179.28(17) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C3 C15 C20 C19 178.93(18) . . . . ?
C18 C19 C20 C15 0.7(3) . . . . ?
C5 C4 C21 C26 -108.33(19) . . . . ?
C3 C4 C21 C26 68.9(2) . . . . ?
C5 C4 C21 C22 71.6(2) . . . . ?
C3 C4 C21 C22 -111.11(18) . . . . ?
C26 C21 C22 C23 2.3(3) . . . . ?
C4 C21 C22 C23 -177.62(17) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 -1.4(3) . . . . ?
C23 C24 C25 C26 1.0(3) . . . . ?
C22 C21 C26 C25 -2.8(3) . . . . ?
C4 C21 C26 C25 177.16(17) . . . . ?
C24 C25 C26 C21 1.2(3) . . . . ?

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
N1 H1B N2 0.89 2.30 3.041(2) 140.8 3_556 yes

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.045



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

data_mo_dd18296_0m
_database_code_depnum_ccdc_archive 'CCDC 2010049'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H18 N2 O S'
_chemical_formula_weight         406.48

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'
S S 0.1246 0.1234 '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                   13.9040(12)
_cell_length_b                   8.1180(7)
_cell_length_c                   18.1962(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.813(3)
_cell_angle_gamma                90
_cell_volume                     2029.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3351
_cell_measurement_theta_min      5.506
_cell_measurement_theta_max      48.572

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6283
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15234
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.753
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3766
_reflns_number_gt                2455
_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)+(0.0415P)²+1.2327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3766
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
S1 S 0.51710(6) 0.41570(11) 0.38851(5) 0.0497(3) Uani 1 1 d . . . . .
O1 O 0.31198(14) 0.1888(3) 0.47922(11) 0.0479(6) Uani 1 1 d . . . . .
N1 N 0.1995(2) 0.0847(4) 0.53884(16) 0.0540(8) Uani 1 1 d . . . . .
H1A H 0.251(3) 0.057(5) 0.573(2) 0.081(14) Uiso 1 1 d . . . . .
H1B H 0.147(3) 0.043(4) 0.544(2) 0.070(13) Uiso 1 1 d . . . . .
N2 N -0.0257(2) 0.1008(4) 0.41827(18) 0.0705(10) Uani 1 1 d . . . . .
C1 C 0.6214(2) 0.3795(4) 0.45090(17) 0.0414(8) Uani 1 1 d . . . . .
C2 C 0.7140(2) 0.4450(4) 0.4479(2) 0.0564(10) Uani 1 1 d . . . . .
H2 H 0.7245 0.5172 0.4103 0.068 Uiso 1 1 calc R U . . .
C3 C 0.7881(3) 0.3994(5) 0.5021(2) 0.0654(11) Uani 1 1 d . . . . .
H3 H 0.8501 0.4419 0.5013 0.079 Uiso 1 1 calc R U . . .
C4 C 0.7737(3) 0.2917(5) 0.5581(2) 0.0671(11) Uani 1 1 d . . . . .
H4 H 0.8257 0.2633 0.5944 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6839(2) 0.2266(5) 0.56070(19) 0.0590(10) Uani 1 1 d . . . . .
H5 H 0.6747 0.1538 0.5985 0.071 Uiso 1 1 calc R U . . .
C6 C 0.6063(2) 0.2696(4) 0.50661(16) 0.0405(8) Uani 1 1 d . . . . .
C7 C 0.5061(2) 0.2144(4) 0.49942(16) 0.0378(7) Uani 1 1 d . . . . .
H7 H 0.4825 0.1417 0.5319 0.045 Uiso 1 1 calc R U . . .
C8 C 0.4500(2) 0.2845(4) 0.43750(16) 0.0365(7) Uani 1 1 d . . . . .
C9 C 0.3447(2) 0.2591(4) 0.41685(16) 0.0384(7) Uani 1 1 d . . . . .
C10 C 0.2859(2) 0.2933(4) 0.35440(16) 0.0386(7) Uani 1 1 d . . . . .
C11 C 0.1757(2) 0.2714(4) 0.34566(16) 0.0417(8) Uani 1 1 d . . . . .
H11 H 0.1461 0.3812 0.3435 0.050 Uiso 1 1 calc R U . . .
C12 C 0.1503(2) 0.1846(4) 0.41379(17) 0.0428(8) Uani 1 1 d . . . . .
C13 C 0.2159(2) 0.1512(4) 0.47469(17) 0.0405(8) Uani 1 1 d . . . . .
C14 C 0.0526(2) 0.1388(4) 0.41571(18) 0.0482(9) Uani 1 1 d . . . . .
C15 C 0.1367(2) 0.1822(4) 0.27382(17) 0.0424(8) Uani 1 1 d . . . . .
C16 C 0.1532(3) 0.0169(5) 0.2658(2) 0.0581(10) Uani 1 1 d . . . . .
H16 H 0.1891 -0.0412 0.3047 0.070 Uiso 1 1 calc R U . . .
C17 C 0.1172(3) -0.0641(5) 0.2006(2) 0.0699(11) Uani 1 1 d . . . . .
H17 H 0.1286 -0.1763 0.1960 0.084 Uiso 1 1 calc R U . . .
C18 C 0.0646(3) 0.0206(6) 0.1425(2) 0.0700(12) Uani 1 1 d . . . . .
H18 H 0.0401 -0.0341 0.0988 0.084 Uiso 1 1 calc R U . . .
C19 C 0.0483(3) 0.1853(6) 0.1493(2) 0.0700(12) Uani 1 1 d . . . . .
H19 H 0.0132 0.2430 0.1099 0.084 Uiso 1 1 calc R U . . .
C20 C 0.0843(2) 0.2672(5) 0.2152(2) 0.0575(10) Uani 1 1 d . . . . .
H20 H 0.0729 0.3794 0.2196 0.069 Uiso 1 1 calc R U . . .
C21 C 0.3241(2) 0.3629(4) 0.28860(16) 0.0395(7) Uani 1 1 d . . . . .
C22 C 0.3071(2) 0.5241(4) 0.26798(18) 0.0510(9) Uani 1 1 d . . . . .
H22 H 0.2687 0.5890 0.2940 0.061 Uiso 1 1 calc R U . . .
C23 C 0.3458(3) 0.5917(5) 0.20981(19) 0.0590(10) Uani 1 1 d . . . . .
H23 H 0.3342 0.7017 0.1973 0.071 Uiso 1 1 calc R U . . .
C24 C 0.4013(2) 0.4972(5) 0.17012(18) 0.0540(9) Uani 1 1 d . . . . .
H24 H 0.4282 0.5433 0.1311 0.065 Uiso 1 1 calc R U . . .
C25 C 0.4170(2) 0.3348(5) 0.18813(18) 0.0542(9) Uani 1 1 d . . . . .
H25 H 0.4539 0.2700 0.1608 0.065 Uiso 1 1 calc R U . . .
C26 C 0.3781(2) 0.2666(4) 0.24700(17) 0.0477(8) Uani 1 1 d . . . . .
H26 H 0.3882 0.1558 0.2586 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.724(3) . ?
S1 C8 1.747(3) . ?
O1 C13 1.360(3) . ?
O1 C9 1.407(3) . ?
N1 C13 1.337(4) . ?
N1 H1A 0.90(4) . ?
N1 H1B 0.82(4) . ?
N2 C14 1.139(4) . ?
C1 C6 1.390(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.364(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(4) . ?
C7 C8 1.390(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.469(4) . ?
C9 C10 1.324(4) . ?
C10 C21 1.493(4) . ?
C10 C11 1.528(4) . ?
C11 C12 1.514(4) . ?
C11 C15 1.520(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.351(4) . ?
C12 C14 1.413(4) . ?
C15 C16 1.373(5) . ?
C15 C20 1.382(4) . ?
C16 C17 1.382(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.372(4) . ?
C21 C26 1.386(4) . ?
C22 C23 1.372(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.367(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(4) . ?
C25 H25 0.9300 . ?
C26 H26 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
C1 S1 C8 91.19(15) . . ?
C13 O1 C9 118.6(2) . . ?
C13 N1 H1A 119(2) . . ?
C13 N1 H1B 123(3) . . ?
H1A N1 H1B 116(4) . . ?
C6 C1 C2 120.9(3) . . ?
C6 C1 S1 112.6(2) . . ?
C2 C1 S1 126.5(3) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 128.2(3) . . ?
C1 C6 C7 112.5(3) . . ?
C8 C7 C6 111.0(3) . . ?
C8 C7 H7 124.5 . . ?
C6 C7 H7 124.5 . . ?
C7 C8 C9 124.3(2) . . ?
C7 C8 S1 112.7(2) . . ?
C9 C8 S1 122.9(2) . . ?
C10 C9 O1 123.0(2) . . ?
C10 C9 C8 130.6(3) . . ?
O1 C9 C8 106.5(2) . . ?
C9 C10 C21 121.3(3) . . ?
C9 C10 C11 122.9(2) . . ?
C21 C10 C11 115.8(3) . . ?
C12 C11 C15 112.7(3) . . ?
C12 C11 C10 109.0(2) . . ?
C15 C11 C10 111.4(2) . . ?
C12 C11 H11 107.9 . . ?
C15 C11 H11 107.9 . . ?
C10 C11 H11 107.9 . . ?
C13 C12 C14 117.2(3) . . ?
C13 C12 C11 123.5(3) . . ?
C14 C12 C11 119.2(3) . . ?
N1 C13 C12 127.8(3) . . ?
N1 C13 O1 109.6(3) . . ?
C12 C13 O1 122.6(3) . . ?
N2 C14 C12 179.0(4) . . ?
C16 C15 C20 118.9(3) . . ?
C16 C15 C11 120.9(3) . . ?
C20 C15 C11 120.2(3) . . ?
C15 C16 C17 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.2(4) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C26 118.3(3) . . ?
C22 C21 C10 120.8(3) . . ?
C26 C21 C10 120.9(3) . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.2(3) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 120.3(3) . . ?
C21 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 S1 C1 C6 0.8(2) . . . . ?
C8 S1 C1 C2 178.9(3) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
S1 C1 C2 C3 -178.9(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
S1 C1 C6 C5 179.3(2) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
S1 C1 C6 C7 -1.0(3) . . . . ?
C5 C6 C7 C8 -179.6(3) . . . . ?
C1 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C9 -177.1(3) . . . . ?
C6 C7 C8 S1 -0.1(3) . . . . ?
C1 S1 C8 C7 -0.4(2) . . . . ?
C1 S1 C8 C9 176.7(2) . . . . ?
C13 O1 C9 C10 1.3(4) . . . . ?
C13 O1 C9 C8 -179.5(2) . . . . ?
C7 C8 C9 C10 -166.9(3) . . . . ?
S1 C8 C9 C10 16.3(5) . . . . ?
C7 C8 C9 O1 14.0(4) . . . . ?
S1 C8 C9 O1 -162.7(2) . . . . ?
O1 C9 C10 C21 -178.0(3) . . . . ?
C8 C9 C10 C21 3.1(5) . . . . ?
O1 C9 C10 C11 4.5(5) . . . . ?
C8 C9 C10 C11 -174.4(3) . . . . ?
C9 C10 C11 C12 -7.9(4) . . . . ?
C21 C10 C11 C12 174.4(3) . . . . ?
C9 C10 C11 C15 -132.9(3) . . . . ?
C21 C10 C11 C15 49.5(4) . . . . ?
C15 C11 C12 C13 130.9(3) . . . . ?
C10 C11 C12 C13 6.7(4) . . . . ?
C15 C11 C12 C14 -50.7(4) . . . . ?
C10 C11 C12 C14 -175.0(3) . . . . ?
C14 C12 C13 N1 -2.8(5) . . . . ?
C11 C12 C13 N1 175.5(3) . . . . ?
C14 C12 C13 O1 179.7(3) . . . . ?
C11 C12 C13 O1 -1.9(5) . . . . ?
C9 O1 C13 N1 179.4(3) . . . . ?
C9 O1 C13 C12 -2.7(4) . . . . ?
C12 C11 C15 C16 -50.7(4) . . . . ?
C10 C11 C15 C16 72.2(4) . . . . ?
C12 C11 C15 C20 129.7(3) . . . . ?
C10 C11 C15 C20 -107.4(3) . . . . ?
C20 C15 C16 C17 -0.8(5) . . . . ?
C11 C15 C16 C17 179.6(3) . . . . ?
C15 C16 C17 C18 0.4(5) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C18 C19 C20 -0.6(6) . . . . ?
C16 C15 C20 C19 0.5(5) . . . . ?
C11 C15 C20 C19 -179.9(3) . . . . ?
C18 C19 C20 C15 0.1(5) . . . . ?
C9 C10 C21 C22 -108.0(4) . . . . ?
C11 C10 C21 C22 69.7(4) . . . . ?
C9 C10 C21 C26 71.7(4) . . . . ?
C11 C10 C21 C26 -110.6(3) . . . . ?
C26 C21 C22 C23 -2.8(5) . . . . ?
C10 C21 C22 C23 176.8(3) . . . . ?
C21 C22 C23 C24 1.1(5) . . . . ?
C22 C23 C24 C25 0.9(6) . . . . ?
C23 C24 C25 C26 -1.0(5) . . . . ?
C22 C21 C26 C25 2.7(5) . . . . ?
C10 C21 C26 C25 -177.0(3) . . . . ?
C24 C25 C26 C21 -0.9(5) . . . . ?

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
N1 H1B N2 0.82(4) 2.25(4) 3.049(4) 166(3) 3_556
N1 H1B N2 0.82(4) 2.25(4) 3.049(4) 166(3) 3_556

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.047

_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_mo_dd19319_0m
_database_code_depnum_ccdc_archive 'CCDC 2010052'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H17 N O S'
_chemical_formula_weight         391.46

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'
S S 0.1246 0.1234 '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                   5.9742(2)
_cell_length_b                   20.6532(6)
_cell_length_c                   16.5404(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.6610(10)
_cell_angle_gamma                90
_cell_volume                     2017.59(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6420
_cell_measurement_theta_min      4.665
_cell_measurement_theta_max      49.929

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6597
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20471
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.491
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3953
_reflns_number_gt                2900
_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)+(0.0482P)²+0.4398P] 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       0.021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3953
_refine_ls_number_parameters     281
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.047
_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
S1 S 0.12184(12) 0.44052(3) 0.45117(5) 0.0626(2) Uani 0.85 1 d . U P A 1
C7 C 0.3571(7) 0.33712(15) 0.4608(2) 0.0689(8) Uani 0.85 1 d . U P A 1
H7 H 0.4707 0.3076 0.4545 0.083 Uiso 0.85 1 calc R U P A 1
S1' S 0.3615(10) 0.3050(2) 0.4525(3) 0.0703(11) Uani 0.15 1 d D U P A 2
C7' C 0.192(3) 0.4232(7) 0.4657(12) 0.070(2) Uani 0.15 1 d D U P A 2
H7' H 0.1762 0.4680 0.4656 0.084 Uiso 0.15 1 calc R U P A 2
O1 O 0.4561(3) 0.48896(6) 0.36756(8) 0.0742(4) Uani 1 1 d . . . . .
N1 N 0.9793(4) 0.56885(10) 0.20184(15) 0.1075(7) Uani 1 1 d . . . . .
C1 C 0.5936(4) 0.52345(10) 0.32654(13) 0.0701(5) Uani 1 1 d . . . . .
H1 H 0.6033 0.5678 0.3359 0.084 Uiso 1 1 calc R U . . .
C2 C 0.7155(3) 0.49865(9) 0.27394(12) 0.0606(5) Uani 1 1 d . . . . .
C3 C 0.7034(3) 0.42805(8) 0.25065(11) 0.0553(4) Uani 1 1 d . . . . .
H3 H 0.8584 0.4113 0.2564 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5784(3) 0.39110(8) 0.30921(10) 0.0510(4) Uani 1 1 d . . . . .
C5 C 0.4663(3) 0.42107(8) 0.36219(11) 0.0567(4) Uani 1 1 d . . . . .
C6 C 0.3374(3) 0.39289(9) 0.42183(11) 0.0569(5) Uani 1 1 d D . . . .
C8 C 0.1905(3) 0.32462(10) 0.51411(11) 0.0665(5) Uani 1 1 d D . . . .
C9 C 0.1506(5) 0.27120(12) 0.56135(15) 0.0942(8) Uani 1 1 d . . . . .
H9 H 0.2394 0.2342 0.5616 0.113 Uiso 1 1 calc R U . . .
C10 C -0.0219(5) 0.27399(14) 0.60755(15) 0.0954(8) Uani 1 1 d . . . . .
H10 H -0.0506 0.2383 0.6386 0.114 Uiso 1 1 calc R U . . .
C11 C -0.1530(4) 0.32856(13) 0.60876(14) 0.0866(7) Uani 1 1 d . . . . .
H11 H -0.2670 0.3295 0.6413 0.104 Uiso 1 1 calc R U . . .
C12 C -0.1178(4) 0.38130(11) 0.56282(13) 0.0779(6) Uani 1 1 d . . . . .
H12 H -0.2076 0.4180 0.5632 0.093 Uiso 1 1 calc R U . . .
C13 C 0.0553(3) 0.37898(9) 0.51534(11) 0.0592(5) Uani 1 1 d . . . . .
C14 C 0.8599(4) 0.53916(10) 0.23490(14) 0.0747(6) Uani 1 1 d . . . . .
C15 C 0.5953(3) 0.41892(9) 0.16217(11) 0.0615(5) Uani 1 1 d . . . . .
C16 C 0.3831(4) 0.44129(14) 0.13483(15) 0.0947(8) Uani 1 1 d . . . . .
H16 H 0.3008 0.4624 0.1704 0.114 Uiso 1 1 calc R U . . .
C17 C 0.2887(6) 0.43231(17) 0.0522(2) 0.1203(10) Uani 1 1 d . . . . .
H17 H 0.1439 0.4474 0.0330 0.144 Uiso 1 1 calc R U . . .
C18 C 0.4109(8) 0.40134(19) 0.00060(18) 0.1267(12) Uani 1 1 d . . . . .
H18 H 0.3489 0.3950 -0.0538 0.152 Uiso 1 1 calc R U . . .
C19 C 0.6189(8) 0.3802(2) 0.0281(2) 0.1471(14) Uani 1 1 d . . . . .
H19 H 0.7016 0.3592 -0.0074 0.177 Uiso 1 1 calc R U . . .
C20 C 0.7122(5) 0.38907(13) 0.10777(15) 0.1024(8) Uani 1 1 d . . . . .
H20 H 0.8586 0.3744 0.1255 0.123 Uiso 1 1 calc R U . . .
C21 C 0.5896(3) 0.31917(8) 0.30541(10) 0.0488(4) Uani 1 1 d . . . . .
C22 C 0.4039(3) 0.28233(9) 0.27492(12) 0.0640(5) Uani 1 1 d . . . . .
H22 H 0.2695 0.3027 0.2530 0.077 Uiso 1 1 calc R U . . .
C23 C 0.4148(4) 0.21562(9) 0.27644(13) 0.0723(6) Uani 1 1 d . . . . .
H23 H 0.2871 0.1914 0.2565 0.087 Uiso 1 1 calc R U . . .
C24 C 0.6121(4) 0.18501(9) 0.30707(12) 0.0675(5) Uani 1 1 d . . . . .
H24 H 0.6186 0.1400 0.3088 0.081 Uiso 1 1 calc R U . . .
C25 C 0.8007(3) 0.22100(9) 0.33524(12) 0.0669(5) Uani 1 1 d . . . . .
H25 H 0.9360 0.2003 0.3553 0.080 Uiso 1 1 calc R U . . .
C26 C 0.7904(3) 0.28765(9) 0.33398(11) 0.0589(5) Uani 1 1 d . . . . .
H26 H 0.9197 0.3117 0.3525 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C13 1.740(2) . ?
S1 C6 1.7464(18) . ?
C7 C6 1.316(4) . ?
C7 C8 1.449(4) . ?
C7 H7 0.9300 . ?
S1' C8 1.601(5) . ?
S1' C6 1.885(5) . ?
C7' C6 1.365(19) . ?
C7' C13 1.542(17) . ?
C7' H7' 0.9300 . ?
O1 C1 1.345(2) . ?
O1 C5 1.407(2) . ?
N1 C14 1.141(3) . ?
C1 C2 1.320(3) . ?
C1 H1 0.9300 . ?
C2 C14 1.424(3) . ?
C2 C3 1.507(2) . ?
C3 C4 1.515(2) . ?
C3 C15 1.520(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.333(2) . ?
C4 C21 1.489(2) . ?
C5 C6 1.461(2) . ?
C8 C13 1.385(3) . ?
C8 C9 1.393(3) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C15 C16 1.361(3) . ?
C15 C20 1.366(3) . ?
C16 C17 1.410(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.331(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.377(2) . ?
C21 C26 1.384(2) . ?
C22 C23 1.379(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(3) . ?
C25 H25 0.9300 . ?
C26 H26 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
C13 S1 C6 90.22(9) . . ?
C6 C7 C8 115.8(3) . . ?
C6 C7 H7 122.1 . . ?
C8 C7 H7 122.1 . . ?
C8 S1' C6 84.1(2) . . ?
C6 C7' C13 116.2(10) . . ?
C6 C7' H7' 121.9 . . ?
C13 C7' H7' 121.9 . . ?
C1 O1 C5 117.40(14) . . ?
C2 C1 O1 124.52(18) . . ?
C2 C1 H1 117.7 . . ?
O1 C1 H1 117.7 . . ?
C1 C2 C14 120.21(18) . . ?
C1 C2 C3 122.27(17) . . ?
C14 C2 C3 117.49(17) . . ?
C2 C3 C4 109.47(14) . . ?
C2 C3 C15 111.30(15) . . ?
C4 C3 C15 111.98(14) . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C15 C3 H3 108.0 . . ?
C5 C4 C21 121.41(16) . . ?
C5 C4 C3 122.08(16) . . ?
C21 C4 C3 116.50(14) . . ?
C4 C5 O1 122.36(16) . . ?
C4 C5 C6 128.84(17) . . ?
O1 C5 C6 108.80(14) . . ?
C7 C6 C5 131.5(2) . . ?
C7' C6 C5 128.2(6) . . ?
C7 C6 S1 111.8(2) . . ?
C5 C6 S1 116.68(13) . . ?
C7' C6 S1' 109.2(7) . . ?
C5 C6 S1' 122.6(2) . . ?
C13 C8 C9 119.0(2) . . ?
C13 C8 C7 108.7(2) . . ?
C9 C8 C7 132.4(2) . . ?
C13 C8 S1' 130.1(2) . . ?
C9 C8 S1' 109.6(3) . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.3(2) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 118.5(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C8 C13 C12 121.42(19) . . ?
C8 C13 C7' 96.7(6) . . ?
C12 C13 C7' 141.2(6) . . ?
C8 C13 S1 113.32(15) . . ?
C12 C13 S1 125.24(16) . . ?
N1 C14 C2 176.5(2) . . ?
C16 C15 C20 118.5(2) . . ?
C16 C15 C3 121.15(18) . . ?
C20 C15 C3 120.3(2) . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 121.5(3) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
C22 C21 C26 118.32(16) . . ?
C22 C21 C4 121.90(15) . . ?
C26 C21 C4 119.78(15) . . ?
C21 C22 C23 120.81(18) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.31(19) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.60(18) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.28(18) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.60(18) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?

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
C5 O1 C1 C2 8.9(3) . . . . ?
O1 C1 C2 C14 -178.66(19) . . . . ?
O1 C1 C2 C3 3.4(3) . . . . ?
C1 C2 C3 C4 -12.5(2) . . . . ?
C14 C2 C3 C4 169.43(17) . . . . ?
C1 C2 C3 C15 111.8(2) . . . . ?
C14 C2 C3 C15 -66.2(2) . . . . ?
C2 C3 C4 C5 10.8(2) . . . . ?
C15 C3 C4 C5 -113.15(19) . . . . ?
C2 C3 C4 C21 -168.47(15) . . . . ?
C15 C3 C4 C21 67.60(19) . . . . ?
C21 C4 C5 O1 179.15(16) . . . . ?
C3 C4 C5 O1 -0.1(3) . . . . ?
C21 C4 C5 C6 -1.2(3) . . . . ?
C3 C4 C5 C6 179.61(17) . . . . ?
C1 O1 C5 C4 -10.5(3) . . . . ?
C1 O1 C5 C6 169.80(17) . . . . ?
C8 C7 C6 C7' 14.4(9) . . . . ?
C8 C7 C6 C5 -177.8(2) . . . . ?
C8 C7 C6 S1 4.3(3) . . . . ?
C8 C7 C6 S1' -124.4(15) . . . . ?
C13 C7' C6 C7 -19.8(14) . . . . ?
C13 C7' C6 C5 171.9(6) . . . . ?
C13 C7' C6 S1 124(4) . . . . ?
C13 C7' C6 S1' -10.3(15) . . . . ?
C4 C5 C6 C7 27.8(4) . . . . ?
O1 C5 C6 C7 -152.5(3) . . . . ?
C4 C5 C6 C7' -167.6(11) . . . . ?
O1 C5 C6 C7' 12.1(11) . . . . ?
C4 C5 C6 S1 -154.36(17) . . . . ?
O1 C5 C6 S1 25.34(19) . . . . ?
C4 C5 C6 S1' 14.9(3) . . . . ?
O1 C5 C6 S1' -165.4(2) . . . . ?
C13 S1 C6 C7 -2.3(2) . . . . ?
C13 S1 C6 C7' -41(3) . . . . ?
C13 S1 C6 C5 179.46(14) . . . . ?
C13 S1 C6 S1' 9.9(2) . . . . ?
C8 S1' C6 C7 42.5(12) . . . . ?
C8 S1' C6 C7' -1.0(10) . . . . ?
C8 S1' C6 C5 176.95(18) . . . . ?
C8 S1' C6 S1 -14.1(3) . . . . ?
C6 C7 C8 C13 -4.4(3) . . . . ?
C6 C7 C8 C9 176.6(2) . . . . ?
C6 C7 C8 S1' 147.5(10) . . . . ?
C6 S1' C8 C13 15.9(4) . . . . ?
C6 S1' C8 C9 -177.41(19) . . . . ?
C6 S1' C8 C7 -19.9(6) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 179.1(3) . . . . ?
S1' C8 C9 C10 -168.3(3) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C9 C8 C13 C12 0.3(3) . . . . ?
C7 C8 C13 C12 -178.9(2) . . . . ?
S1' C8 C13 C12 166.0(3) . . . . ?
C9 C8 C13 C7' 172.2(8) . . . . ?
C7 C8 C13 C7' -6.9(8) . . . . ?
S1' C8 C13 C7' -22.1(9) . . . . ?
C9 C8 C13 S1 -178.40(17) . . . . ?
C7 C8 C13 S1 2.5(2) . . . . ?
S1' C8 C13 S1 -12.7(4) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C11 C12 C13 C7' -167.2(12) . . . . ?
C11 C12 C13 S1 178.49(17) . . . . ?
C6 C7' C13 C8 17.4(14) . . . . ?
C6 C7' C13 C12 -173.6(4) . . . . ?
C6 C7' C13 S1 -135(3) . . . . ?
C6 S1 C13 C8 -0.26(15) . . . . ?
C6 S1 C13 C12 -178.86(18) . . . . ?
C6 S1 C13 C7' 30(2) . . . . ?
C2 C3 C15 C16 -57.8(2) . . . . ?
C4 C3 C15 C16 65.1(2) . . . . ?
C2 C3 C15 C20 120.8(2) . . . . ?
C4 C3 C15 C20 -116.3(2) . . . . ?
C20 C15 C16 C17 1.0(4) . . . . ?
C3 C15 C16 C17 179.6(2) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 0.2(6) . . . . ?
C18 C19 C20 C15 0.9(6) . . . . ?
C16 C15 C20 C19 -1.4(4) . . . . ?
C3 C15 C20 C19 179.9(3) . . . . ?
C5 C4 C21 C22 71.1(2) . . . . ?
C3 C4 C21 C22 -109.67(19) . . . . ?
C5 C4 C21 C26 -108.2(2) . . . . ?
C3 C4 C21 C26 71.1(2) . . . . ?
C26 C21 C22 C23 3.1(3) . . . . ?
C4 C21 C22 C23 -176.17(18) . . . . ?
C21 C22 C23 C24 -1.2(3) . . . . ?
C22 C23 C24 C25 -1.0(3) . . . . ?
C23 C24 C25 C26 1.1(3) . . . . ?
C24 C25 C26 C21 0.9(3) . . . . ?
C22 C21 C26 C25 -3.0(3) . . . . ?
C4 C21 C26 C25 176.32(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12 S1 0.93 2.98 3.687(2) 133.9 3_566
C12 H12 S1 0.93 2.98 3.687(2) 133.9 3_566
C12 H12 S1 0.93 2.98 3.687(2) 133.9 3_566

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.031

_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_mo_dd19348_0m
_database_code_depnum_ccdc_archive 'CCDC 2010050'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H17 N O2'
_chemical_formula_weight         375.40

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                   5.8562(2)
_cell_length_b                   20.4312(6)
_cell_length_c                   16.4731(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.0920(10)
_cell_angle_gamma                90
_cell_volume                     1946.23(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6441
_cell_measurement_theta_min      5.009
_cell_measurement_theta_max      48.408

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6988
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23860
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.504
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3813
_reflns_number_gt                2715
_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)+(0.0522P)²+0.4070P] 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       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3813
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.5313(2) 0.52289(6) 0.62597(8) 0.0699(4) Uani 1 1 d . . . . .
O2 O 0.8293(2) 0.57934(6) 0.55058(8) 0.0634(4) Uani 1 1 d . . . . .
N1 N -0.0027(4) 0.44477(9) 0.79269(14) 0.1020(7) Uani 1 1 d . . . . .
C1 C 0.3847(3) 0.48938(9) 0.66605(12) 0.0662(5) Uani 1 1 d . . . . .
H1 H 0.3640 0.4451 0.6541 0.079 Uiso 1 1 calc R U . . .
C2 C 0.2685(3) 0.51481(8) 0.72099(11) 0.0579(5) Uani 1 1 d . . . . .
C3 C 0.2948(3) 0.58531(7) 0.74789(11) 0.0531(4) Uani 1 1 d . . . . .
H3 H 0.1402 0.6048 0.7419 0.064 Uiso 1 1 calc R U . . .
C4 C 0.4316(3) 0.62169(8) 0.69156(10) 0.0492(4) Uani 1 1 d . . . . .
C5 C 0.5387(3) 0.59100(8) 0.63687(11) 0.0537(4) Uani 1 1 d . . . . .
C6 C 0.6705(3) 0.62050(8) 0.57858(10) 0.0536(4) Uani 1 1 d . . . . .
C7 C 0.6734(3) 0.68000(9) 0.54414(11) 0.0608(5) Uani 1 1 d . . . . .
H7 H 0.5816 0.7155 0.5533 0.073 Uiso 1 1 calc R U . . .
C8 C 0.8432(3) 0.67868(9) 0.49085(10) 0.0556(4) Uani 1 1 d . . . . .
C9 C 0.9330(4) 0.72377(10) 0.44045(12) 0.0742(6) Uani 1 1 d . . . . .
H9 H 0.8785 0.7666 0.4357 0.089 Uiso 1 1 calc R U . . .
C10 C 1.1036(4) 0.70310(11) 0.39827(12) 0.0774(6) Uani 1 1 d . . . . .
H10 H 1.1658 0.7325 0.3647 0.093 Uiso 1 1 calc R U . . .
C11 C 1.1852(4) 0.63965(11) 0.40448(12) 0.0749(6) Uani 1 1 d . . . . .
H11 H 1.2986 0.6272 0.3740 0.090 Uiso 1 1 calc R U . . .
C12 C 1.1039(3) 0.59463(10) 0.45421(13) 0.0718(5) Uani 1 1 d . . . . .
H12 H 1.1600 0.5520 0.4591 0.086 Uiso 1 1 calc R U . . .
C13 C 0.9340(3) 0.61622(8) 0.49671(10) 0.0557(4) Uani 1 1 d . . . . .
C14 C 0.1184(4) 0.47466(9) 0.75971(14) 0.0720(6) Uani 1 1 d . . . . .
C15 C 0.4044(3) 0.59111(8) 0.83756(11) 0.0565(4) Uani 1 1 d . . . . .
C16 C 0.2937(4) 0.62254(12) 0.89324(14) 0.0913(7) Uani 1 1 d . . . . .
H16 H 0.1484 0.6406 0.8759 0.110 Uiso 1 1 calc R U . . .
C17 C 0.3915(7) 0.62806(18) 0.97362(19) 0.1304(11) Uani 1 1 d . . . . .
H17 H 0.3129 0.6504 1.0099 0.157 Uiso 1 1 calc R U . . .
C18 C 0.5993(7) 0.60181(17) 1.00138(17) 0.1162(10) Uani 1 1 d . . . . .
H18 H 0.6632 0.6053 1.0566 0.139 Uiso 1 1 calc R U . . .
C19 C 0.7160(5) 0.56993(15) 0.94746(18) 0.1107(9) Uani 1 1 d . . . . .
H19 H 0.8605 0.5517 0.9659 0.133 Uiso 1 1 calc R U . . .
C20 C 0.6182(4) 0.56474(12) 0.86480(14) 0.0886(7) Uani 1 1 d . . . . .
H20 H 0.6982 0.5434 0.8281 0.106 Uiso 1 1 calc R U . . .
C21 C 0.4340(3) 0.69434(7) 0.69878(9) 0.0454(4) Uani 1 1 d . . . . .
C22 C 0.2351(3) 0.72902(8) 0.66951(11) 0.0564(4) Uani 1 1 d . . . . .
H22 H 0.1014 0.7065 0.6476 0.068 Uiso 1 1 calc R U . . .
C23 C 0.2321(3) 0.79631(9) 0.67233(12) 0.0629(5) Uani 1 1 d . . . . .
H23 H 0.0969 0.8189 0.6524 0.075 Uiso 1 1 calc R U . . .
C24 C 0.4269(3) 0.83006(9) 0.70430(11) 0.0633(5) Uani 1 1 d . . . . .
H24 H 0.4260 0.8756 0.7050 0.076 Uiso 1 1 calc R U . . .
C25 C 0.6234(3) 0.79643(9) 0.73536(12) 0.0676(5) Uani 1 1 d . . . . .
H25 H 0.7555 0.8193 0.7581 0.081 Uiso 1 1 calc R U . . .
C26 C 0.6276(3) 0.72891(8) 0.73329(11) 0.0593(5) Uani 1 1 d . . . . .
H26 H 0.7616 0.7066 0.7553 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.349(2) . ?
O1 C5 1.4027(19) . ?
O2 C13 1.379(2) . ?
O2 C6 1.3859(19) . ?
N1 C14 1.137(2) . ?
C1 C2 1.322(2) . ?
C1 H1 0.9300 . ?
C2 C14 1.424(3) . ?
C2 C3 1.508(2) . ?
C3 C4 1.513(2) . ?
C3 C15 1.519(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.333(2) . ?
C4 C21 1.489(2) . ?
C5 C6 1.454(2) . ?
C6 C7 1.343(2) . ?
C7 C8 1.427(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.380(2) . ?
C8 C9 1.397(3) . ?
C9 C10 1.371(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C15 C16 1.364(3) . ?
C15 C20 1.372(3) . ?
C16 C17 1.362(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.343(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.395(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.380(2) . ?
C21 C22 1.383(2) . ?
C22 C23 1.376(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.365(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.368(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.380(2) . ?
C25 H25 0.9300 . ?
C26 H26 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
C1 O1 C5 116.75(13) . . ?
C13 O2 C6 105.81(13) . . ?
C2 C1 O1 124.88(16) . . ?
C2 C1 H1 117.6 . . ?
O1 C1 H1 117.6 . . ?
C1 C2 C14 120.09(16) . . ?
C1 C2 C3 122.46(16) . . ?
C14 C2 C3 117.40(16) . . ?
C2 C3 C4 109.18(14) . . ?
C2 C3 C15 111.60(14) . . ?
C4 C3 C15 112.01(13) . . ?
C2 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C15 C3 H3 108.0 . . ?
C5 C4 C21 121.56(15) . . ?
C5 C4 C3 122.31(14) . . ?
C21 C4 C3 116.10(13) . . ?
C4 C5 O1 123.00(15) . . ?
C4 C5 C6 127.35(15) . . ?
O1 C5 C6 109.61(14) . . ?
C7 C6 O2 110.77(15) . . ?
C7 C6 C5 134.25(16) . . ?
O2 C6 C5 114.98(14) . . ?
C6 C7 C8 107.43(16) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 H7 126.3 . . ?
C13 C8 C9 118.31(17) . . ?
C13 C8 C7 105.83(15) . . ?
C9 C8 C7 135.84(17) . . ?
C10 C9 C8 118.10(19) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 121.8(2) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 115.94(19) . . ?
C11 C12 H12 122.0 . . ?
C13 C12 H12 122.0 . . ?
C12 C13 O2 125.62(17) . . ?
C12 C13 C8 124.21(18) . . ?
O2 C13 C8 110.16(15) . . ?
N1 C14 C2 177.1(2) . . ?
C16 C15 C20 118.1(2) . . ?
C16 C15 C3 121.18(18) . . ?
C20 C15 C3 120.72(17) . . ?
C15 C16 C17 121.4(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 119.2(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.1(2) . . ?
C15 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C26 C21 C22 118.25(15) . . ?
C26 C21 C4 122.68(14) . . ?
C22 C21 C4 119.07(14) . . ?
C23 C22 C21 120.96(16) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 120.23(16) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 119.51(16) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 120.66(16) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C21 C26 C25 120.34(16) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 C2 -7.7(3) . . . . ?
O1 C1 C2 C14 -179.87(18) . . . . ?
O1 C1 C2 C3 -2.5(3) . . . . ?
C1 C2 C3 C4 10.7(2) . . . . ?
C14 C2 C3 C4 -171.81(16) . . . . ?
C1 C2 C3 C15 -113.6(2) . . . . ?
C14 C2 C3 C15 63.8(2) . . . . ?
C2 C3 C4 C5 -9.9(2) . . . . ?
C15 C3 C4 C5 114.24(17) . . . . ?
C2 C3 C4 C21 168.29(13) . . . . ?
C15 C3 C4 C21 -67.58(17) . . . . ?
C21 C4 C5 O1 -177.09(14) . . . . ?
C3 C4 C5 O1 1.0(2) . . . . ?
C21 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 178.62(15) . . . . ?
C1 O1 C5 C4 8.4(2) . . . . ?
C1 O1 C5 C6 -169.57(15) . . . . ?
C13 O2 C6 C7 0.28(18) . . . . ?
C13 O2 C6 C5 179.92(13) . . . . ?
C4 C5 C6 C7 -22.8(3) . . . . ?
O1 C5 C6 C7 155.07(19) . . . . ?
C4 C5 C6 O2 157.66(16) . . . . ?
O1 C5 C6 O2 -24.5(2) . . . . ?
O2 C6 C7 C8 -0.30(19) . . . . ?
C5 C6 C7 C8 -179.84(18) . . . . ?
C6 C7 C8 C13 0.19(19) . . . . ?
C6 C7 C8 C9 -177.7(2) . . . . ?
C13 C8 C9 C10 1.2(3) . . . . ?
C7 C8 C9 C10 178.98(19) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C13 0.8(3) . . . . ?
C11 C12 C13 O2 -179.43(17) . . . . ?
C11 C12 C13 C8 0.8(3) . . . . ?
C6 O2 C13 C12 -179.93(16) . . . . ?
C6 O2 C13 C8 -0.15(18) . . . . ?
C9 C8 C13 C12 -1.9(3) . . . . ?
C7 C8 C13 C12 179.76(17) . . . . ?
C9 C8 C13 O2 178.34(15) . . . . ?
C7 C8 C13 O2 -0.02(19) . . . . ?
C2 C3 C15 C16 -121.8(2) . . . . ?
C4 C3 C15 C16 115.4(2) . . . . ?
C2 C3 C15 C20 58.2(2) . . . . ?
C4 C3 C15 C20 -64.6(2) . . . . ?
C20 C15 C16 C17 0.2(4) . . . . ?
C3 C15 C16 C17 -179.8(2) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
C16 C17 C18 C19 1.1(5) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
C16 C15 C20 C19 0.5(3) . . . . ?
C3 C15 C20 C19 -179.5(2) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
C5 C4 C21 C26 -73.2(2) . . . . ?
C3 C4 C21 C26 108.61(18) . . . . ?
C5 C4 C21 C22 106.49(19) . . . . ?
C3 C4 C21 C22 -71.70(19) . . . . ?
C26 C21 C22 C23 2.0(3) . . . . ?
C4 C21 C22 C23 -177.70(16) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 C25 -1.6(3) . . . . ?
C23 C24 C25 C26 1.2(3) . . . . ?
C22 C21 C26 C25 -2.4(3) . . . . ?
C4 C21 C26 C25 177.28(17) . . . . ?
C24 C25 C26 C21 0.9(3) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.026

_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_ddz20150
_database_code_depnum_ccdc_archive 'CCDC 2058996'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;College of Chemistry and Materials Engineering, Wenzhou University
China
;
_audit_update_record             
;
2021-01-27 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H15 N O S'
_chemical_formula_weight         389.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   10.3399(5)
_cell_length_b                   21.2956(10)
_cell_length_c                   8.7889(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.714(2)
_cell_angle_gamma                90
_cell_volume                     1894.96(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5551
_cell_measurement_theta_min      4.455
_cell_measurement_theta_max      53.325

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5831
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18922
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3721
_reflns_number_gt                2747
_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)+(0.0307P)²+0.5541P] 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       0.0101(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3721
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03537(5) 0.41312(2) 0.66454(6) 0.04930(18) Uani 1 1 d . . . . .
O1 O 0.09528(14) 0.52365(7) 0.85904(16) 0.0555(4) Uani 1 1 d . . . . .
N1 N 0.2072(2) 0.70756(10) 1.1585(3) 0.0859(7) Uani 1 1 d . . . . .
C1 C 0.07533(19) 0.37350(9) 0.5080(2) 0.0452(5) Uani 1 1 d . . . . .
C2 C 0.0227(2) 0.31551(10) 0.4549(3) 0.0555(6) Uani 1 1 d . . . . .
H2 H -0.0383 0.2954 0.5026 0.067 Uiso 1 1 calc R U . . .
C3 C 0.0630(2) 0.28866(11) 0.3303(3) 0.0639(6) Uani 1 1 d . . . . .
H3 H 0.0282 0.2502 0.2919 0.077 Uiso 1 1 calc R U . . .
C4 C 0.1550(2) 0.31851(11) 0.2617(3) 0.0667(6) Uani 1 1 d . . . . .
H4 H 0.1826 0.2994 0.1786 0.080 Uiso 1 1 calc R U . . .
C5 C 0.2068(2) 0.37609(11) 0.3139(3) 0.0589(6) Uani 1 1 d . . . . .
H5 H 0.2685 0.3953 0.2656 0.071 Uiso 1 1 calc R U . . .
C6 C 0.16713(18) 0.40574(9) 0.4389(2) 0.0438(5) Uani 1 1 d . . . . .
C7 C 0.20378(17) 0.46591(9) 0.5159(2) 0.0407(4) Uani 1 1 d . . . . .
C8 C 0.28683(18) 0.51604(9) 0.4827(2) 0.0427(5) Uani 1 1 d . . . . .
C9 C 0.3505(2) 0.51509(11) 0.3560(2) 0.0571(6) Uani 1 1 d . . . . .
H9 H 0.3405 0.4802 0.2910 0.069 Uiso 1 1 calc R U . . .
C10 C 0.4265(2) 0.56401(12) 0.3257(3) 0.0655(6) Uani 1 1 d . . . . .
H10 H 0.4684 0.5618 0.2417 0.079 Uiso 1 1 calc R U . . .
C11 C 0.4419(2) 0.61682(11) 0.4188(3) 0.0620(6) Uani 1 1 d . . . . .
H11 H 0.4932 0.6501 0.3965 0.074 Uiso 1 1 calc R U . . .
C12 C 0.3820(2) 0.62019(10) 0.5434(2) 0.0521(5) Uani 1 1 d . . . . .
H12 H 0.3926 0.6561 0.6049 0.062 Uiso 1 1 calc R U . . .
C13 C 0.30417(18) 0.57023(9) 0.5805(2) 0.0416(5) Uani 1 1 d . . . . .
C14 C 0.24354(18) 0.57416(8) 0.7140(2) 0.0414(5) Uani 1 1 d . . . . .
C15 C 0.16306(18) 0.52642(9) 0.7375(2) 0.0424(5) Uani 1 1 d . . . . .
C16 C 0.14120(18) 0.47359(9) 0.6399(2) 0.0406(4) Uani 1 1 d . . . . .
C17 C 0.1126(2) 0.57286(10) 0.9591(3) 0.0560(6) Uani 1 1 d . . . . .
H17 H 0.0682 0.5719 1.0411 0.067 Uiso 1 1 calc R U . . .
C18 C 0.18813(19) 0.62201(9) 0.9484(2) 0.0483(5) Uani 1 1 d . . . . .
C19 C 0.26910(19) 0.62973(9) 0.8238(2) 0.0444(5) Uani 1 1 d . . . . .
H19 H 0.2389 0.6678 0.7645 0.053 Uiso 1 1 calc R U . . .
C20 C 0.41357(19) 0.63880(9) 0.9016(2) 0.0449(5) Uani 1 1 d . . . . .
C21 C 0.4596(2) 0.69867(10) 0.9440(3) 0.0699(7) Uani 1 1 d . . . . .
H21 H 0.4041 0.7330 0.9173 0.084 Uiso 1 1 calc R U . . .
C22 C 0.5869(3) 0.70783(13) 1.0255(3) 0.0885(9) Uani 1 1 d . . . . .
H22 H 0.6163 0.7482 1.0544 0.106 Uiso 1 1 calc R U . . .
C23 C 0.6699(2) 0.65791(14) 1.0639(3) 0.0764(8) Uani 1 1 d . . . . .
H23 H 0.7554 0.6642 1.1198 0.092 Uiso 1 1 calc R U . . .
C24 C 0.6267(2) 0.59839(12) 1.0199(3) 0.0608(6) Uani 1 1 d . . . . .
H24 H 0.6838 0.5644 1.0443 0.073 Uiso 1 1 calc R U . . .
C25 C 0.49870(19) 0.58873(10) 0.9393(2) 0.0484(5) Uani 1 1 d . . . . .
H25 H 0.4699 0.5483 0.9105 0.058 Uiso 1 1 calc R U . . .
C26 C 0.1972(2) 0.66935(11) 1.0662(3) 0.0614(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
S1 C16 1.7316(19) . ?
S1 C1 1.734(2) . ?
O1 C17 1.357(2) . ?
O1 C15 1.393(2) . ?
N1 C26 1.139(3) . ?
C1 C2 1.391(3) . ?
C1 C6 1.405(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(3) . ?
C7 C16 1.385(3) . ?
C7 C8 1.437(3) . ?
C8 C9 1.404(3) . ?
C8 C13 1.428(3) . ?
C9 C10 1.363(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.411(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.440(3) . ?
C14 C15 1.356(3) . ?
C14 C19 1.516(3) . ?
C15 C16 1.405(3) . ?
C17 C18 1.320(3) . ?
C17 H17 0.9300 . ?
C18 C26 1.434(3) . ?
C18 C19 1.516(3) . ?
C19 C20 1.524(3) . ?
C19 H19 0.9800 . ?
C20 C25 1.380(3) . ?
C20 C21 1.385(3) . ?
C21 C22 1.378(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.373(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9300 . ?
C25 H25 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
C16 S1 C1 90.24(9) . . ?
C17 O1 C15 116.33(16) . . ?
C2 C1 C6 122.74(19) . . ?
C2 C1 S1 123.96(17) . . ?
C6 C1 S1 113.30(14) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 116.76(18) . . ?
C5 C6 C7 131.99(19) . . ?
C1 C6 C7 111.25(17) . . ?
C16 C7 C8 117.77(17) . . ?
C16 C7 C6 110.41(17) . . ?
C8 C7 C6 131.79(18) . . ?
C9 C8 C13 117.85(18) . . ?
C9 C8 C7 123.10(19) . . ?
C13 C8 C7 119.04(18) . . ?
C10 C9 C8 121.7(2) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 121.2(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 118.53(18) . . ?
C12 C13 C14 120.49(18) . . ?
C8 C13 C14 120.98(17) . . ?
C15 C14 C13 117.55(17) . . ?
C15 C14 C19 121.41(18) . . ?
C13 C14 C19 121.04(17) . . ?
C14 C15 O1 124.65(18) . . ?
C14 C15 C16 122.36(18) . . ?
O1 C15 C16 112.99(16) . . ?
C7 C16 C15 122.12(17) . . ?
C7 C16 S1 114.74(14) . . ?
C15 C16 S1 123.13(15) . . ?
C18 C17 O1 124.6(2) . . ?
C18 C17 H17 117.7 . . ?
O1 C17 H17 117.7 . . ?
C17 C18 C26 117.3(2) . . ?
C17 C18 C19 123.97(19) . . ?
C26 C18 C19 118.68(19) . . ?
C18 C19 C14 108.95(16) . . ?
C18 C19 C20 108.96(16) . . ?
C14 C19 C20 114.38(15) . . ?
C18 C19 H19 108.1 . . ?
C14 C19 H19 108.1 . . ?
C20 C19 H19 108.1 . . ?
C25 C20 C21 118.61(19) . . ?
C25 C20 C19 121.97(17) . . ?
C21 C20 C19 119.31(17) . . ?
C22 C21 C20 120.7(2) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.3(2) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.2(2) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C20 C25 C24 120.4(2) . . ?
C20 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
N1 C26 C18 178.3(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
C16 S1 C1 C2 179.91(17) . . . . ?
C16 S1 C1 C6 -0.02(14) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
S1 C1 C2 C3 -179.53(16) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
S1 C1 C6 C5 178.56(15) . . . . ?
C2 C1 C6 C7 178.87(17) . . . . ?
S1 C1 C6 C7 -1.2(2) . . . . ?
C5 C6 C7 C16 -177.6(2) . . . . ?
C1 C6 C7 C16 2.1(2) . . . . ?
C5 C6 C7 C8 4.2(3) . . . . ?
C1 C6 C7 C8 -176.08(18) . . . . ?
C16 C7 C8 C9 -176.91(18) . . . . ?
C6 C7 C8 C9 1.2(3) . . . . ?
C16 C7 C8 C13 1.8(2) . . . . ?
C6 C7 C8 C13 179.89(17) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C10 178.6(2) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C8 -1.2(3) . . . . ?
C11 C12 C13 C14 178.93(18) . . . . ?
C9 C8 C13 C12 1.1(3) . . . . ?
C7 C8 C13 C12 -177.67(16) . . . . ?
C9 C8 C13 C14 -179.08(17) . . . . ?
C7 C8 C13 C14 2.2(3) . . . . ?
C12 C13 C14 C15 175.79(17) . . . . ?
C8 C13 C14 C15 -4.0(2) . . . . ?
C12 C13 C14 C19 -4.2(3) . . . . ?
C8 C13 C14 C19 175.95(16) . . . . ?
C13 C14 C15 O1 -178.81(16) . . . . ?
C19 C14 C15 O1 1.2(3) . . . . ?
C13 C14 C15 C16 2.0(3) . . . . ?
C19 C14 C15 C16 -178.00(16) . . . . ?
C17 O1 C15 C14 0.1(3) . . . . ?
C17 O1 C15 C16 179.39(16) . . . . ?
C8 C7 C16 C15 -3.9(3) . . . . ?
C6 C7 C16 C15 177.58(16) . . . . ?
C8 C7 C16 S1 176.28(13) . . . . ?
C6 C7 C16 S1 -2.22(19) . . . . ?
C14 C15 C16 C7 2.1(3) . . . . ?
O1 C15 C16 C7 -177.24(16) . . . . ?
C14 C15 C16 S1 -178.17(14) . . . . ?
O1 C15 C16 S1 2.5(2) . . . . ?
C1 S1 C16 C7 1.33(14) . . . . ?
C1 S1 C16 C15 -178.46(16) . . . . ?
C15 O1 C17 C18 0.0(3) . . . . ?
O1 C17 C18 C26 -178.83(19) . . . . ?
O1 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C14 2.4(3) . . . . ?
C26 C18 C19 C14 179.78(17) . . . . ?
C17 C18 C19 C20 -123.0(2) . . . . ?
C26 C18 C19 C20 54.4(2) . . . . ?
C15 C14 C19 C18 -2.3(2) . . . . ?
C13 C14 C19 C18 177.75(15) . . . . ?
C15 C14 C19 C20 119.93(19) . . . . ?
C13 C14 C19 C20 -60.1(2) . . . . ?
C18 C19 C20 C25 89.2(2) . . . . ?
C14 C19 C20 C25 -32.9(3) . . . . ?
C18 C19 C20 C21 -87.0(2) . . . . ?
C14 C19 C20 C21 150.9(2) . . . . ?
C25 C20 C21 C22 -1.5(4) . . . . ?
C19 C20 C21 C22 174.8(2) . . . . ?
C20 C21 C22 C23 0.7(4) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C21 C20 C25 C24 0.9(3) . . . . ?
C19 C20 C25 C24 -175.32(19) . . . . ?
C23 C24 C25 C20 0.5(3) . . . . ?

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 S1 0.93 3.01 3.928(2) 168.9 3_567
C17 H17 S1 0.93 3.01 3.928(2) 168.9 3_567

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.035

_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_mo_dd18167_0m
_database_code_depnum_ccdc_archive 'CCDC 2010051'
loop_
_audit_author_name
_audit_author_address
'Xiaobo Huang'
;Wenzhou University 
China
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2021-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N2 O'
_chemical_formula_weight         350.40

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

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

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

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

_cell_length_a                   32.1003(8)
_cell_length_b                   5.9107(2)
_cell_length_c                   19.8365(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.1180(10)
_cell_angle_gamma                90
_cell_volume                     3705.15(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      4.502
_cell_measurement_theta_max      54.466

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39121
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.578
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3639
_reflns_number_gt                3045
_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)+(0.0402P)²+1.9036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3639
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54650(3) 0.44760(16) 0.66776(4) 0.0444(2) Uani 1 1 d . . . . .
N1 N 0.49656(4) 0.5864(2) 0.58680(6) 0.0463(3) Uani 1 1 d . . . . .
H1A H 0.4871(5) 0.668(3) 0.5490(9) 0.061(5) Uiso 1 1 d . . . . .
H1B H 0.4821(6) 0.470(3) 0.5979(9) 0.073(6) Uiso 1 1 d . . . . .
N2 N 0.54426(4) 1.1107(2) 0.53115(6) 0.0562(3) Uani 1 1 d . . . . .
C1 C 0.53659(4) 0.6101(2) 0.61947(6) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.56474(4) 0.7715(2) 0.60992(6) 0.0381(3) Uani 1 1 d . . . . .
C3 C 0.61062(4) 0.7590(2) 0.64470(6) 0.0386(3) Uani 1 1 d . . . . .
H3 H 0.6196 0.9117 0.6602 0.046 Uiso 1 1 calc R U . . .
C4 C 0.61474(4) 0.6078(2) 0.70733(6) 0.0372(3) Uani 1 1 d . . . . .
C5 C 0.58390(4) 0.4671(2) 0.71640(6) 0.0367(3) Uani 1 1 d . . . . .
C6 C 0.58109(4) 0.3099(2) 0.77343(6) 0.0370(3) Uani 1 1 d . . . . .
C7 C 0.60036(5) 0.3555(3) 0.84043(7) 0.0482(3) Uani 1 1 d . . . . .
H7 H 0.6159 0.4879 0.8504 0.058 Uiso 1 1 calc R U . . .
C8 C 0.59654(5) 0.2050(3) 0.89216(7) 0.0593(4) Uani 1 1 d . . . . .
H8 H 0.6095 0.2368 0.9369 0.071 Uiso 1 1 calc R U . . .
C9 C 0.57371(5) 0.0083(3) 0.87822(8) 0.0595(4) Uani 1 1 d . . . . .
H9 H 0.5715 -0.0933 0.9133 0.071 Uiso 1 1 calc R U . . .
C10 C 0.55417(5) -0.0375(3) 0.81244(8) 0.0539(4) Uani 1 1 d . . . . .
H10 H 0.5386 -0.1699 0.8029 0.065 Uiso 1 1 calc R U . . .
C11 C 0.55756(4) 0.1123(2) 0.76028(7) 0.0436(3) Uani 1 1 d . . . . .
H11 H 0.5440 0.0807 0.7159 0.052 Uiso 1 1 calc R U . . .
C12 C 0.65601(4) 0.6285(2) 0.75525(6) 0.0389(3) Uani 1 1 d . . . . .
C13 C 0.68653(5) 0.4610(3) 0.75979(8) 0.0520(4) Uani 1 1 d . . . . .
H13 H 0.6809 0.3294 0.7341 0.062 Uiso 1 1 calc R U . . .
C14 C 0.72530(5) 0.4878(3) 0.80229(9) 0.0627(4) Uani 1 1 d . . . . .
H14 H 0.7456 0.3743 0.8049 0.075 Uiso 1 1 calc R U . . .
C15 C 0.73393(5) 0.6803(3) 0.84053(8) 0.0599(4) Uani 1 1 d . . . . .
H15 H 0.7600 0.6973 0.8692 0.072 Uiso 1 1 calc R U . . .
C16 C 0.70398(5) 0.8486(3) 0.83648(8) 0.0593(4) Uani 1 1 d . . . . .
H16 H 0.7097 0.9793 0.8626 0.071 Uiso 1 1 calc R U . . .
C17 C 0.66545(4) 0.8233(3) 0.79369(7) 0.0498(4) Uani 1 1 d . . . . .
H17 H 0.6455 0.9387 0.7906 0.060 Uiso 1 1 calc R U . . .
C18 C 0.63944(4) 0.6785(2) 0.59612(6) 0.0405(3) Uani 1 1 d . . . . .
C19 C 0.67246(5) 0.8095(3) 0.58363(9) 0.0668(5) Uani 1 1 d . . . . .
H19 H 0.6776 0.9485 0.6055 0.080 Uiso 1 1 calc R U . . .
C20 C 0.69824(6) 0.7373(5) 0.53891(12) 0.0961(8) Uani 1 1 d . . . . .
H20 H 0.7205 0.8285 0.5310 0.115 Uiso 1 1 calc R U . . .
C21 C 0.69143(6) 0.5343(4) 0.50633(10) 0.0801(6) Uani 1 1 d . . . . .
H21 H 0.7089 0.4867 0.4763 0.096 Uiso 1 1 calc R U . . .
C22 C 0.65867(6) 0.4016(3) 0.51824(9) 0.0674(5) Uani 1 1 d . . . . .
H22 H 0.6537 0.2629 0.4962 0.081 Uiso 1 1 calc R U . . .
C23 C 0.63289(5) 0.4729(3) 0.56300(8) 0.0562(4) Uani 1 1 d . . . . .
H23 H 0.6107 0.3809 0.5709 0.067 Uiso 1 1 calc R U . . .
C24 C 0.55254(4) 0.9546(2) 0.56524(7) 0.0406(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 C1 1.3544(15) . ?
O1 C5 1.4066(14) . ?
N1 C1 1.3412(16) . ?
N1 H1A 0.897(18) . ?
N1 H1B 0.88(2) . ?
N2 C24 1.1473(17) . ?
C1 C2 1.3500(18) . ?
C2 C24 1.4100(18) . ?
C2 C3 1.5144(17) . ?
C3 C4 1.5172(17) . ?
C3 C18 1.5248(19) . ?
C3 H3 0.9800 . ?
C4 C5 1.3293(18) . ?
C4 C12 1.4938(17) . ?
C5 C6 1.4786(17) . ?
C6 C7 1.3902(18) . ?
C6 C11 1.3908(19) . ?
C7 C8 1.380(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.3804(19) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.3846(19) . ?
C12 C17 1.385(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.3797(19) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.370(2) . ?
C18 C23 1.380(2) . ?
C19 C20 1.383(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.362(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.366(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.382(2) . ?
C22 H22 0.9300 . ?
C23 H23 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
C1 O1 C5 119.55(10) . . ?
C1 N1 H1A 120.2(11) . . ?
C1 N1 H1B 117.7(12) . . ?
H1A N1 H1B 120.8(16) . . ?
N1 C1 C2 127.88(12) . . ?
N1 C1 O1 110.72(12) . . ?
C2 C1 O1 121.38(11) . . ?
C1 C2 C24 120.80(11) . . ?
C1 C2 C3 121.53(11) . . ?
C24 C2 C3 117.65(11) . . ?
C2 C3 C4 109.85(10) . . ?
C2 C3 C18 112.14(10) . . ?
C4 C3 C18 110.99(11) . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C18 C3 H3 107.9 . . ?
C5 C4 C12 124.29(11) . . ?
C5 C4 C3 121.31(11) . . ?
C12 C4 C3 114.39(10) . . ?
C4 C5 O1 121.64(11) . . ?
C4 C5 C6 130.07(11) . . ?
O1 C5 C6 108.29(10) . . ?
C7 C6 C11 118.55(12) . . ?
C7 C6 C5 122.20(12) . . ?
C11 C6 C5 119.23(11) . . ?
C8 C7 C6 120.22(14) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.59(14) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 119.74(14) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.23(14) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.65(13) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C13 C12 C17 118.34(12) . . ?
C13 C12 C4 121.42(12) . . ?
C17 C12 C4 120.15(12) . . ?
C14 C13 C12 120.54(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.36(15) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.83(14) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.94(15) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.99(14) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19 C18 C23 118.03(14) . . ?
C19 C18 C3 120.82(14) . . ?
C23 C18 C3 121.15(12) . . ?
C18 C19 C20 120.73(18) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 120.79(18) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.22(18) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 120.16(18) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 121.08(15) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
N2 C24 C2 176.22(15) . . ?

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
C5 O1 C1 N1 -167.87(11) . . . . ?
C5 O1 C1 C2 10.60(18) . . . . ?
N1 C1 C2 C24 5.7(2) . . . . ?
O1 C1 C2 C24 -172.51(12) . . . . ?
N1 C1 C2 C3 -172.28(13) . . . . ?
O1 C1 C2 C3 9.53(19) . . . . ?
C1 C2 C3 C4 -21.77(17) . . . . ?
C24 C2 C3 C4 160.21(12) . . . . ?
C1 C2 C3 C18 102.15(14) . . . . ?
C24 C2 C3 C18 -75.87(15) . . . . ?
C2 C3 C4 C5 16.09(17) . . . . ?
C18 C3 C4 C5 -108.49(14) . . . . ?
C2 C3 C4 C12 -165.28(11) . . . . ?
C18 C3 C4 C12 70.13(14) . . . . ?
C12 C4 C5 O1 -176.94(11) . . . . ?
C3 C4 C5 O1 1.5(2) . . . . ?
C12 C4 C5 C6 2.7(2) . . . . ?
C3 C4 C5 C6 -178.84(12) . . . . ?
C1 O1 C5 C4 -16.43(18) . . . . ?
C1 O1 C5 C6 163.88(11) . . . . ?
C4 C5 C6 C7 31.6(2) . . . . ?
O1 C5 C6 C7 -148.79(12) . . . . ?
C4 C5 C6 C11 -150.07(14) . . . . ?
O1 C5 C6 C11 29.58(16) . . . . ?
C11 C6 C7 C8 1.0(2) . . . . ?
C5 C6 C7 C8 179.35(14) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C6 0.6(2) . . . . ?
C7 C6 C11 C10 -1.3(2) . . . . ?
C5 C6 C11 C10 -179.74(13) . . . . ?
C5 C4 C12 C13 72.28(19) . . . . ?
C3 C4 C12 C13 -106.30(15) . . . . ?
C5 C4 C12 C17 -111.25(16) . . . . ?
C3 C4 C12 C17 70.17(16) . . . . ?
C17 C12 C13 C14 0.6(2) . . . . ?
C4 C12 C13 C14 177.14(14) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C12 1.1(2) . . . . ?
C13 C12 C17 C16 -1.2(2) . . . . ?
C4 C12 C17 C16 -177.78(14) . . . . ?
C2 C3 C18 C19 121.73(15) . . . . ?
C4 C3 C18 C19 -114.98(15) . . . . ?
C2 C3 C18 C23 -57.68(16) . . . . ?
C4 C3 C18 C23 65.60(15) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
C3 C18 C19 C20 -179.20(17) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C19 C18 C23 C22 -0.4(2) . . . . ?
C3 C18 C23 C22 179.08(14) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?

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
N1 H1A N2 0.897(18) 2.166(18) 3.0524(18) 169.1(15) 5_676
N1 H1A N2 0.897(18) 2.166(18) 3.0524(18) 169.1(15) 5_676
N1 H1A N2 0.897(18) 2.166(18) 3.0524(18) 169.1(15) 5_676
N1 H1A N2 0.897(18) 2.166(18) 3.0524(18) 169.1(15) 5_676
N1 H1A N2 0.897(18) 2.166(18) 3.0524(18) 169.1(15) 5_676

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4



