# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_11683
_database_code_depnum_ccdc_archive 'CCDC 2083118'
loop_
_audit_author_name
_audit_author_address
DONGa
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-05-12 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 N O3'
_chemical_formula_weight         411.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   24.355(2)
_cell_length_b                   6.4076(7)
_cell_length_c                   13.2555(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2068.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1302
_cell_measurement_theta_min      3.6170
_cell_measurement_theta_max      54.4350

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.682
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_T_min  0.83625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12326
_diffrn_reflns_av_unetI/netI     0.1343
_diffrn_reflns_av_R_equivalents  0.1340
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.630
_diffrn_reflns_theta_max         67.229
_diffrn_reflns_theta_full        67.229
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.910
_reflns_number_total             3375
_reflns_number_gt                1495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.812
_reflns_Friedel_fraction_full    0.812

_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1042P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0088(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3375
_refine_ls_number_parameters     282
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1635
_refine_ls_R_factor_gt           0.0842
_refine_ls_wR_factor_ref         0.2664
_refine_ls_wR_factor_gt          0.1873
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_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
N1 N 0.8281(4) -0.0022(13) 0.9465(8) 0.063(2) Uani 1 1 d . . . . .
O1 O 0.9357(4) 0.7522(13) 0.5740(7) 0.092(3) Uani 1 1 d . . . . .
O2 O 0.8537(3) 0.6037(13) 0.5211(6) 0.080(3) Uani 1 1 d . . . . .
O3 O 0.8539(4) 0.0798(14) 0.7802(6) 0.086(3) Uani 1 1 d . . . . .
C1 C 0.8875(6) 0.787(2) 0.5146(12) 0.098(5) Uani 1 1 d . . . . .
H1A H 0.897509 0.813372 0.444940 0.117 Uiso 1 1 calc R U . . .
H1B H 0.867627 0.907463 0.539871 0.117 Uiso 1 1 calc R U . . .
C2 C 0.9211(5) 0.5889(17) 0.6375(10) 0.067(3) Uani 1 1 d . . . . .
C3 C 0.9500(5) 0.5102(17) 0.7184(9) 0.064(3) Uani 1 1 d . . . . .
H3 H 0.982948 0.570154 0.738874 0.077 Uiso 1 1 calc R U . . .
C4 C 0.9281(4) 0.3364(17) 0.7691(8) 0.059(3) Uani 1 1 d . . . . .
C5 C 0.8787(4) 0.2492(17) 0.7340(8) 0.056(3) Uani 1 1 d . . . . .
C6 C 0.8509(4) 0.3261(18) 0.6515(9) 0.067(3) Uani 1 1 d . . . . .
H6 H 0.818658 0.264393 0.628453 0.081 Uiso 1 1 calc R U . . .
C7 C 0.8728(5) 0.4979(18) 0.6051(9) 0.067(3) Uani 1 1 d . . . . .
C8 C 0.9560(4) 0.2461(17) 0.8594(8) 0.058(3) Uani 1 1 d . . . . .
H8 H 0.973316 0.360851 0.896459 0.070 Uiso 1 1 calc R U . . .
C9 C 1.0003(5) 0.0765(17) 0.8405(8) 0.061(3) Uani 1 1 d . . . . .
C10 C 1.0382(4) 0.0690(19) 0.7642(9) 0.066(3) Uani 1 1 d . . . . .
H10 H 1.038484 0.168591 0.713202 0.079 Uiso 1 1 calc R U . . .
C11 C 1.0772(5) -0.096(2) 0.7657(10) 0.080(4) Uani 1 1 d . . . . .
H11 H 1.103317 -0.106137 0.714813 0.096 Uiso 1 1 calc R U . . .
C12 C 1.0764(5) -0.242(2) 0.8426(10) 0.076(3) Uani 1 1 d . . . . .
H12 H 1.101736 -0.351110 0.843029 0.091 Uiso 1 1 calc R U . . .
C13 C 1.0375(5) -0.2261(18) 0.9195(9) 0.069(3) Uani 1 1 d . . . . .
H13 H 1.037283 -0.322647 0.971887 0.083 Uiso 1 1 calc R U . . .
C14 C 1.0002(4) -0.0698(17) 0.9177(8) 0.061(3) Uani 1 1 d . . . . .
C15 C 0.9551(4) -0.0160(16) 0.9937(8) 0.060(3) Uani 1 1 d . . . . .
H15A H 0.970140 0.054301 1.052375 0.073 Uiso 1 1 calc R U . . .
H15B H 0.935634 -0.140173 1.015451 0.073 Uiso 1 1 calc R U . . .
C16 C 0.9171(4) 0.1311(15) 0.9326(8) 0.053(2) Uani 1 1 d . . . . .
C17 C 0.8728(4) -0.0011(16) 0.8762(9) 0.057(3) Uani 1 1 d . . . . .
H17 H 0.886315 -0.143850 0.867009 0.068 Uiso 1 1 calc R U . . .
C18 C 0.8300(5) 0.1761(16) 1.0065(8) 0.063(3) Uani 1 1 d . . . . .
C19 C 0.7897(5) 0.2604(18) 1.0693(10) 0.075(3) Uani 1 1 d . . . . .
H19 H 0.755057 0.200614 1.074727 0.090 Uiso 1 1 calc R U . . .
C20 C 0.8038(5) 0.4362(17) 1.1228(10) 0.073(3) Uani 1 1 d . . . . .
H20 H 0.777282 0.496937 1.163924 0.088 Uiso 1 1 calc R U . . .
C21 C 0.8550(5) 0.5275(18) 1.1189(10) 0.076(3) Uani 1 1 d . . . . .
H21 H 0.862945 0.644332 1.157954 0.091 Uiso 1 1 calc R U . . .
C22 C 0.8948(5) 0.4413(16) 1.0553(9) 0.069(3) Uani 1 1 d . . . . .
H22 H 0.929457 0.501616 1.049906 0.083 Uiso 1 1 calc R U . . .
C23 C 0.8818(5) 0.2665(16) 1.0011(8) 0.059(3) Uani 1 1 d . . . . .
C24 C 0.7764(4) -0.1142(16) 0.9300(10) 0.068(3) Uani 1 1 d . . . . .
H24A H 0.750640 -0.019177 0.898267 0.082 Uiso 1 1 calc R U . . .
H24B H 0.761330 -0.151822 0.995286 0.082 Uiso 1 1 calc R U . . .
C25 C 0.7798(4) -0.3042(17) 0.8681(10) 0.069(3) Uani 1 1 d . . . . .
H25A H 0.807868 -0.395967 0.894956 0.083 Uiso 1 1 calc R U . . .
H25B H 0.789912 -0.267459 0.799555 0.083 Uiso 1 1 calc R U . . .
C26 C 0.7244(4) -0.4168(17) 0.8678(12) 0.079(3) Uani 1 1 d . . . . .
H26A H 0.696048 -0.319229 0.847346 0.095 Uiso 1 1 calc R U . . .
H26B H 0.716043 -0.462157 0.935926 0.095 Uiso 1 1 calc R U . . .
C27 C 0.7228(6) -0.6064(19) 0.7975(11) 0.087(4) Uani 1 1 d . . . . .
H27A H 0.725209 -0.560547 0.728725 0.131 Uiso 1 1 calc R U . . .
H27B H 0.689012 -0.680890 0.807334 0.131 Uiso 1 1 calc R U . . .
H27C H 0.753182 -0.696743 0.812456 0.131 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.393(13) . ?
N1 C17 1.432(13) . ?
N1 C24 1.467(12) . ?
O1 C2 1.389(13) . ?
O1 C1 1.432(14) . ?
O2 C7 1.385(13) . ?
O2 C1 1.438(14) . ?
O3 C5 1.385(13) . ?
O3 C17 1.448(14) . ?
C2 C3 1.379(15) . ?
C2 C7 1.382(15) . ?
C3 C4 1.406(14) . ?
C4 C5 1.406(14) . ?
C4 C8 1.493(14) . ?
C5 C6 1.377(15) . ?
C6 C7 1.370(16) . ?
C8 C16 1.543(14) . ?
C8 C9 1.552(15) . ?
C9 C10 1.370(15) . ?
C9 C14 1.388(14) . ?
C10 C11 1.422(16) . ?
C11 C12 1.385(18) . ?
C12 C13 1.395(16) . ?
C13 C14 1.353(15) . ?
C14 C15 1.529(15) . ?
C15 C16 1.550(13) . ?
C16 C23 1.523(14) . ?
C16 C17 1.563(14) . ?
C18 C23 1.389(14) . ?
C18 C19 1.395(15) . ?
C19 C20 1.374(15) . ?
C20 C21 1.379(15) . ?
C21 C22 1.399(15) . ?
C22 C23 1.369(14) . ?
C24 C25 1.471(14) . ?
C25 C26 1.530(13) . ?
C26 C27 1.531(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 N1 C17 110.1(9) . . ?
C18 N1 C24 120.9(9) . . ?
C17 N1 C24 123.9(10) . . ?
C2 O1 C1 103.9(9) . . ?
C7 O2 C1 104.8(9) . . ?
C5 O3 C17 122.1(9) . . ?
O1 C1 O2 108.0(9) . . ?
C3 C2 C7 121.4(11) . . ?
C3 C2 O1 128.1(10) . . ?
C7 C2 O1 110.4(10) . . ?
C2 C3 C4 117.9(10) . . ?
C5 C4 C3 118.8(10) . . ?
C5 C4 C8 120.1(10) . . ?
C3 C4 C8 121.1(9) . . ?
C6 C5 O3 114.6(10) . . ?
C6 C5 C4 122.8(10) . . ?
O3 C5 C4 122.5(10) . . ?
C7 C6 C5 116.8(11) . . ?
C6 C7 C2 122.2(12) . . ?
C6 C7 O2 128.5(11) . . ?
C2 C7 O2 109.3(10) . . ?
C4 C8 C16 114.2(8) . . ?
C4 C8 C9 117.3(9) . . ?
C16 C8 C9 101.2(8) . . ?
C10 C9 C14 121.5(11) . . ?
C10 C9 C8 127.8(10) . . ?
C14 C9 C8 110.6(9) . . ?
C9 C10 C11 117.7(11) . . ?
C12 C11 C10 120.4(12) . . ?
C11 C12 C13 119.7(12) . . ?
C14 C13 C12 120.0(12) . . ?
C13 C14 C9 120.7(10) . . ?
C13 C14 C15 129.6(11) . . ?
C9 C14 C15 109.6(9) . . ?
C14 C15 C16 102.8(9) . . ?
C23 C16 C8 116.7(8) . . ?
C23 C16 C15 111.9(9) . . ?
C8 C16 C15 104.7(8) . . ?
C23 C16 C17 101.7(9) . . ?
C8 C16 C17 112.5(9) . . ?
C15 C16 C17 109.5(8) . . ?
N1 C17 O3 109.5(9) . . ?
N1 C17 C16 102.5(9) . . ?
O3 C17 C16 116.4(8) . . ?
C23 C18 N1 110.0(10) . . ?
C23 C18 C19 120.5(10) . . ?
N1 C18 C19 129.5(11) . . ?
C20 C19 C18 116.7(11) . . ?
C19 C20 C21 123.6(12) . . ?
C20 C21 C22 118.8(12) . . ?
C23 C22 C21 118.6(11) . . ?
C22 C23 C18 121.7(10) . . ?
C22 C23 C16 130.4(11) . . ?
C18 C23 C16 107.9(9) . . ?
N1 C24 C25 116.1(9) . . ?
C24 C25 C26 110.0(9) . . ?
C25 C26 C27 113.4(10) . . ?

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_exp_12437
_database_code_depnum_ccdc_archive 'CCDC 2112489'
loop_
_audit_author_name
_audit_author_address
dong
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-09-28 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 N2 O'
_chemical_formula_weight         364.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.2685(8)
_cell_length_b                   18.7779(14)
_cell_length_c                   10.9806(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.311(9)
_cell_angle_gamma                90
_cell_volume                     1874.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1074
_cell_measurement_theta_min      4.6940
_cell_measurement_theta_max      68.7490

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.621
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_T_min  0.82891
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6628
_diffrn_reflns_av_unetI/netI     0.0915
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.710
_diffrn_reflns_theta_max         67.243
_diffrn_reflns_theta_full        67.243
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3353
_reflns_number_gt                1697
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00169(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3353
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.983
_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
N1 N 0.4184(3) 0.28834(15) -0.0010(2) 0.0491(7) Uani 1 1 d . . . . .
N2 N -0.2173(3) 0.14227(18) -0.0003(3) 0.0668(9) Uani 1 1 d . . . . .
H2A H -0.306682 0.146965 -0.039523 0.080 Uiso 1 1 calc R U . . .
O1 O 0.2629(2) 0.18301(11) 0.19855(18) 0.0488(6) Uani 1 1 d . . . . .
C1 C 0.4139(3) 0.16914(19) 0.0427(3) 0.0489(9) Uani 1 1 d . . . . .
C2 C 0.4108(4) 0.09805(19) 0.0151(3) 0.0590(10) Uani 1 1 d . . . . .
H2 H 0.403466 0.064295 0.075570 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4188(4) 0.0771(2) -0.1046(4) 0.0637(11) Uani 1 1 d . . . . .
H3 H 0.416897 0.029047 -0.125123 0.076 Uiso 1 1 calc R U . . .
C4 C 0.4296(4) 0.1279(2) -0.1927(3) 0.0582(10) Uani 1 1 d . . . . .
H4 H 0.436116 0.113122 -0.272337 0.070 Uiso 1 1 calc R U . . .
C5 C 0.4312(3) 0.20022(19) -0.1671(3) 0.0516(9) Uani 1 1 d . . . . .
H5 H 0.438341 0.233944 -0.227668 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4217(3) 0.22016(18) -0.0471(3) 0.0460(8) Uani 1 1 d . . . . .
C7 C 0.3641(4) 0.34721(19) -0.0833(3) 0.0689(12) Uani 1 1 d . . . . .
H7A H 0.282505 0.330614 -0.146191 0.083 Uiso 1 1 calc R U . . .
H7B H 0.441520 0.362735 -0.125186 0.083 Uiso 1 1 calc R U . . .
C8 C 0.3140(4) 0.40959(19) -0.0167(3) 0.0540(9) Uani 1 1 d . . . . .
C9 C 0.3171(4) 0.47789(19) -0.0660(3) 0.0663(11) Uani 1 1 d . . . . .
H9 H 0.349438 0.484329 -0.140292 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2731(4) 0.5355(2) -0.0062(4) 0.0718(12) Uani 1 1 d . . . . .
H10 H 0.274498 0.580731 -0.040579 0.086 Uiso 1 1 calc R U . . .
C11 C 0.2269(4) 0.5270(2) 0.1047(4) 0.0677(11) Uani 1 1 d . . . . .
H11 H 0.198449 0.566210 0.145977 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2232(4) 0.45903(19) 0.1542(3) 0.0610(10) Uani 1 1 d . . . . .
H12 H 0.191437 0.453030 0.228799 0.073 Uiso 1 1 calc R U . . .
C13 C 0.2662(4) 0.40002(18) 0.0942(3) 0.0498(9) Uani 1 1 d . . . . .
C14 C 0.2659(4) 0.32563(17) 0.1465(3) 0.0463(8) Uani 1 1 d . . . . .
H14 H 0.268381 0.330369 0.235802 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4061(3) 0.28673(18) 0.1318(3) 0.0466(8) Uani 1 1 d . . . . .
C16 C 0.3975(3) 0.20497(17) 0.1603(3) 0.0492(9) Uani 1 1 d . . . . .
H16 H 0.481466 0.192111 0.225726 0.059 Uiso 1 1 calc R U . . .
C17 C 0.1369(3) 0.21053(18) 0.1235(3) 0.0425(8) Uani 1 1 d . . . . .
C18 C 0.0163(4) 0.16561(18) 0.0893(3) 0.0462(8) Uani 1 1 d . . . . .
C19 C -0.0117(4) 0.09188(19) 0.1056(3) 0.0593(10) Uani 1 1 d . . . . .
H19 H 0.054627 0.058323 0.146011 0.071 Uiso 1 1 calc R U . . .
C20 C -0.1542(4) 0.0803(2) 0.0503(4) 0.0702(12) Uani 1 1 d . . . . .
H20 H -0.202028 0.036566 0.047329 0.084 Uiso 1 1 calc R U . . .
C21 C -0.1139(4) 0.1958(2) 0.0222(3) 0.0508(9) Uani 1 1 d . . . . .
C22 C -0.1245(4) 0.26738(19) -0.0126(3) 0.0541(9) Uani 1 1 d . . . . .
H22 H -0.211610 0.286305 -0.057493 0.065 Uiso 1 1 calc R U . . .
C23 C -0.0008(4) 0.30887(19) 0.0224(3) 0.0512(9) Uani 1 1 d . . . . .
H23 H -0.004306 0.356518 -0.001077 0.061 Uiso 1 1 calc R U . . .
C24 C 0.1305(4) 0.28142(17) 0.0924(3) 0.0436(8) Uani 1 1 d . . . . .
C25 C 0.5442(4) 0.31941(19) 0.2120(3) 0.0674(11) Uani 1 1 d . . . . .
H25A H 0.629762 0.294653 0.197168 0.101 Uiso 1 1 calc R U . . .
H25B H 0.538658 0.315282 0.298069 0.101 Uiso 1 1 calc R U . . .
H25C H 0.550767 0.368762 0.190905 0.101 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.379(4) . ?
N1 C7 1.454(4) . ?
N1 C15 1.485(4) . ?
N2 C20 1.371(4) . ?
N2 C21 1.378(4) . ?
O1 C17 1.390(3) . ?
O1 C16 1.452(3) . ?
C1 C2 1.368(4) . ?
C1 C6 1.387(4) . ?
C1 C16 1.490(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.376(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.389(4) . ?
C7 C8 1.502(4) . ?
C8 C13 1.386(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.370(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.511(4) . ?
C14 C24 1.525(4) . ?
C14 C15 1.527(4) . ?
C15 C25 1.532(4) . ?
C15 C16 1.572(4) . ?
C17 C24 1.373(4) . ?
C17 C18 1.391(4) . ?
C18 C21 1.405(4) . ?
C18 C19 1.426(4) . ?
C19 C20 1.359(5) . ?
C21 C22 1.395(4) . ?
C22 C23 1.377(4) . ?
C23 C24 1.403(4) . ?

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
C6 N1 C7 120.5(3) . . ?
C6 N1 C15 110.7(3) . . ?
C7 N1 C15 122.8(3) . . ?
C20 N2 C21 108.7(3) . . ?
C17 O1 C16 113.1(2) . . ?
C2 C1 C6 121.2(3) . . ?
C2 C1 C16 129.1(3) . . ?
C6 C1 C16 109.5(3) . . ?
C1 C2 C3 118.9(3) . . ?
C4 C3 C2 119.7(4) . . ?
C3 C4 C5 122.3(3) . . ?
C4 C5 C6 117.2(3) . . ?
N1 C6 C1 111.8(3) . . ?
N1 C6 C5 127.5(3) . . ?
C1 C6 C5 120.7(3) . . ?
N1 C7 C8 113.1(3) . . ?
C13 C8 C9 119.7(3) . . ?
C13 C8 C7 120.6(3) . . ?
C9 C8 C7 119.7(3) . . ?
C10 C9 C8 120.6(3) . . ?
C9 C10 C11 120.4(4) . . ?
C10 C11 C12 119.3(4) . . ?
C13 C12 C11 121.1(3) . . ?
C8 C13 C12 119.0(3) . . ?
C8 C13 C14 118.6(3) . . ?
C12 C13 C14 122.4(3) . . ?
C13 C14 C24 114.7(3) . . ?
C13 C14 C15 109.7(3) . . ?
C24 C14 C15 110.6(3) . . ?
N1 C15 C14 109.0(3) . . ?
N1 C15 C25 109.9(3) . . ?
C14 C15 C25 112.3(3) . . ?
N1 C15 C16 103.4(3) . . ?
C14 C15 C16 111.6(3) . . ?
C25 C15 C16 110.2(3) . . ?
O1 C16 C1 111.2(3) . . ?
O1 C16 C15 114.5(3) . . ?
C1 C16 C15 104.5(3) . . ?
C24 C17 O1 119.9(3) . . ?
C24 C17 C18 121.9(3) . . ?
O1 C17 C18 118.1(3) . . ?
C17 C18 C21 117.3(3) . . ?
C17 C18 C19 135.3(3) . . ?
C21 C18 C19 107.4(3) . . ?
C20 C19 C18 106.6(4) . . ?
C19 C20 N2 110.2(3) . . ?
N2 C21 C22 130.2(3) . . ?
N2 C21 C18 107.2(3) . . ?
C22 C21 C18 122.7(3) . . ?
C23 C22 C21 117.3(3) . . ?
C22 C23 C24 122.0(3) . . ?
C17 C24 C23 118.9(3) . . ?
C17 C24 C14 116.1(3) . . ?
C23 C24 C14 124.9(3) . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_10439
_database_code_depnum_ccdc_archive 'CCDC 2083117'
loop_
_audit_author_name
_audit_author_address
DONGc
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-05-12 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 N O3'
_chemical_formula_weight         355.38

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           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                   11.9483(6)
_cell_length_b                   17.9325(13)
_cell_length_c                   16.0130(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.010(6)
_cell_angle_gamma                90
_cell_volume                     3431.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1598
_cell_measurement_theta_min      4.4140
_cell_measurement_theta_max      70.1420

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.738
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_T_min  0.95293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10183
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.447
_diffrn_reflns_theta_max         67.222
_diffrn_reflns_theta_full        67.222
_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             3056
_reflns_number_gt                1702
_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       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0951
_refine_ls_wR_factor_ref         0.3137
_refine_ls_wR_factor_gt          0.2612
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
N1 N 0.9544(3) 0.4435(3) 0.3760(3) 0.0710(11) Uani 1 1 d . . . . .
O1 O 0.6326(4) 0.3578(2) 0.1091(2) 0.0914(13) Uani 1 1 d . . . . .
O2 O 0.5824(3) 0.4815(2) 0.1104(2) 0.0776(10) Uani 1 1 d . . . . .
O3 O 0.7049(3) 0.5196(2) 0.3927(2) 0.0720(10) Uani 1 1 d . . . . .
C1 C 0.5636(5) 0.4122(3) 0.0686(3) 0.0789(15) Uani 1 1 d . . . . .
H1A H 0.583452 0.416296 0.010062 0.095 Uiso 1 1 calc R U . . .
H1B H 0.485365 0.398085 0.072539 0.095 Uiso 1 1 calc R U . . .
C2 C 0.6268(3) 0.4612(3) 0.1861(3) 0.0576(11) Uani 1 1 d . . . . .
C3 C 0.6449(4) 0.5074(3) 0.2540(3) 0.0656(12) Uani 1 1 d . . . . .
H3 H 0.623924 0.557293 0.253794 0.079 Uiso 1 1 calc R U . . .
C4 C 0.6962(4) 0.4747(3) 0.3222(3) 0.0606(11) Uani 1 1 d . . . . .
C5 C 0.7285(4) 0.4014(3) 0.3237(3) 0.0610(11) Uani 1 1 d . . . . .
C6 C 0.7104(4) 0.3565(3) 0.2537(3) 0.0667(12) Uani 1 1 d . . . . .
H6 H 0.733994 0.307037 0.252459 0.080 Uiso 1 1 calc R U . . .
C7 C 0.6558(4) 0.3887(3) 0.1860(3) 0.0678(12) Uani 1 1 d . . . . .
C8 C 0.8082(4) 0.5131(3) 0.4397(3) 0.0684(13) Uani 1 1 d . . . . .
H8 H 0.793825 0.525515 0.498275 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8984(5) 0.5629(3) 0.4067(3) 0.0708(13) Uani 1 1 d . . . . .
C10 C 0.9072(6) 0.6400(4) 0.4061(4) 0.0939(18) Uani 1 1 d . . . . .
H10 H 0.852175 0.669624 0.430233 0.113 Uiso 1 1 calc R U . . .
C11 C 0.9995(7) 0.6715(4) 0.3687(5) 0.101(2) Uani 1 1 d . . . . .
H11 H 1.005469 0.723149 0.366193 0.121 Uiso 1 1 calc R U . . .
C12 C 1.0821(7) 0.6288(4) 0.3355(4) 0.105(2) Uani 1 1 d . . . . .
H12 H 1.144059 0.652226 0.312092 0.125 Uiso 1 1 calc R U . . .
C13 C 1.0774(5) 0.5510(4) 0.3354(4) 0.0842(16) Uani 1 1 d . . . . .
H13 H 1.134086 0.521669 0.312916 0.101 Uiso 1 1 calc R U . . .
C14 C 0.9813(4) 0.5204(3) 0.3713(3) 0.0648(12) Uani 1 1 d . . . . .
C15 C 1.0310(4) 0.3847(3) 0.3658(3) 0.0762(14) Uani 1 1 d . . . . .
H15A H 1.088913 0.388284 0.408063 0.091 Uiso 1 1 calc R U . . .
H15B H 1.066360 0.388624 0.311464 0.091 Uiso 1 1 calc R U . . .
C16 C 0.9741(4) 0.3119(3) 0.3729(3) 0.0694(13) Uani 1 1 d . . . . .
C17 C 1.0354(6) 0.2447(4) 0.3650(4) 0.0885(17) Uani 1 1 d . . . . .
H17 H 1.111590 0.247975 0.353934 0.106 Uiso 1 1 calc R U . . .
C18 C 0.9899(7) 0.1762(4) 0.3727(3) 0.093(2) Uani 1 1 d . . . . .
H18 H 1.033478 0.133676 0.366093 0.112 Uiso 1 1 calc R U . . .
C19 C 0.8754(7) 0.1707(4) 0.3908(4) 0.100(2) Uani 1 1 d . . . . .
H19 H 0.842470 0.124037 0.397331 0.120 Uiso 1 1 calc R U . . .
C20 C 0.8110(6) 0.2348(3) 0.3988(4) 0.0838(16) Uani 1 1 d . . . . .
H20 H 0.734726 0.230936 0.409718 0.101 Uiso 1 1 calc R U . . .
C21 C 0.8596(4) 0.3041(3) 0.3908(3) 0.0679(13) Uani 1 1 d . . . . .
C22 C 0.7873(4) 0.3731(3) 0.4027(3) 0.0637(12) Uani 1 1 d . . . . .
H22 H 0.730466 0.362431 0.445160 0.076 Uiso 1 1 calc R U . . .
C23 C 0.8625(4) 0.4336(3) 0.4346(3) 0.0615(12) Uani 1 1 d . . . . .
H23 H 0.892113 0.419569 0.489471 0.074 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C15 1.406(7) . ?
N1 C14 1.419(7) . ?
N1 C23 1.456(6) . ?
O1 C7 1.379(6) . ?
O1 C1 1.433(7) . ?
O2 C2 1.371(5) . ?
O2 C1 1.430(7) . ?
O3 C4 1.391(5) . ?
O3 C8 1.450(6) . ?
C2 C7 1.346(7) . ?
C2 C3 1.384(6) . ?
C3 C4 1.382(7) . ?
C4 C5 1.369(7) . ?
C5 C6 1.398(6) . ?
C5 C22 1.532(6) . ?
C6 C7 1.391(7) . ?
C8 C9 1.495(7) . ?
C8 C23 1.568(7) . ?
C9 C14 1.372(8) . ?
C9 C10 1.387(8) . ?
C10 C11 1.376(10) . ?
C11 C12 1.357(10) . ?
C12 C13 1.397(10) . ?
C13 C14 1.396(8) . ?
C15 C16 1.477(8) . ?
C16 C21 1.405(7) . ?
C16 C17 1.415(7) . ?
C17 C18 1.348(9) . ?
C18 C19 1.402(10) . ?
C19 C20 1.390(9) . ?
C20 C21 1.377(8) . ?
C21 C22 1.522(7) . ?
C22 C23 1.498(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N1 C14 125.2(4) . . ?
C15 N1 C23 118.3(4) . . ?
C14 N1 C23 108.9(4) . . ?
C7 O1 C1 104.2(4) . . ?
C2 O2 C1 104.1(4) . . ?
C4 O3 C8 116.0(3) . . ?
O2 C1 O1 106.8(4) . . ?
C7 C2 O2 110.8(4) . . ?
C7 C2 C3 122.5(4) . . ?
O2 C2 C3 126.6(4) . . ?
C4 C3 C2 115.9(5) . . ?
C5 C4 C3 123.1(4) . . ?
C5 C4 O3 121.3(4) . . ?
C3 C4 O3 115.4(4) . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 C22 117.5(4) . . ?
C6 C5 C22 122.8(4) . . ?
C7 C6 C5 117.2(5) . . ?
C2 C7 O1 109.7(4) . . ?
C2 C7 C6 121.5(4) . . ?
O1 C7 C6 128.6(5) . . ?
O3 C8 C9 112.4(4) . . ?
O3 C8 C23 113.5(4) . . ?
C9 C8 C23 103.1(4) . . ?
C14 C9 C10 119.6(6) . . ?
C14 C9 C8 109.6(4) . . ?
C10 C9 C8 130.8(6) . . ?
C11 C10 C9 118.3(7) . . ?
C12 C11 C10 121.4(7) . . ?
C11 C12 C13 122.3(7) . . ?
C14 C13 C12 115.1(6) . . ?
C9 C14 C13 123.2(5) . . ?
C9 C14 N1 110.7(4) . . ?
C13 C14 N1 126.1(5) . . ?
N1 C15 C16 110.8(4) . . ?
C21 C16 C17 115.9(6) . . ?
C21 C16 C15 123.5(4) . . ?
C17 C16 C15 120.5(5) . . ?
C18 C17 C16 124.0(7) . . ?
C17 C18 C19 118.5(6) . . ?
C20 C19 C18 120.0(7) . . ?
C21 C20 C19 120.3(7) . . ?
C20 C21 C16 121.3(5) . . ?
C20 C21 C22 118.9(5) . . ?
C16 C21 C22 119.8(4) . . ?
C23 C22 C21 106.9(4) . . ?
C23 C22 C5 108.5(4) . . ?
C21 C22 C5 115.3(4) . . ?
N1 C23 C22 108.7(4) . . ?
N1 C23 C8 103.6(4) . . ?
C22 C23 C8 115.3(4) . . ?

_refine_diff_density_max         0.756
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.071

