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

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

data_230505b_0m
_database_code_depnum_ccdc_archive 'CCDC 2326905'
loop_
_audit_author_name
_audit_author_address
'Yuqing Xiao'
;Central China Normal University
China
;
_audit_update_record             
;
2024-01-20 deposited with the CCDC.	2025-07-03 downloaded from the CCDC.
;
_audit_creation_date             2023-05-10
_audit_creation_method           
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Cl N O3'
_chemical_formula_sum            'C21 H18 Cl N O3'
_chemical_formula_weight         367.81
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9050(6)
_cell_length_b                   10.3232(11)
_cell_length_c                   14.2771(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.286(2)
_cell_angle_gamma                90
_cell_volume                     865.08(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9775
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.27
_cell_measurement_theta_min      3.73
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    1.402
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS, Madison WI for PHOTON III'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30058
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         72.716
_diffrn_reflns_theta_min         5.424
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from θ/2θ scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                4938
_reflns_number_total             4971
_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. 
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_molecular_graphics    
'Bruker SHELXTL Bruker-AXS, Madison WI and local programs'
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.204
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2246 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.003(9)
_refine_ls_extinction_coef       0.223(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4971
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.193
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0866P)²+0.0605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C10(H10A,H10B), C11(H11A,H11B), C14(H14A,H14B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C16(H16), C17(H17), C19(H19), 
 C20(H20) 
2.c Idealised Me refined as rotating group: 
 C22(H22A,H22B,H22C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2771(3) 0.40444(17) 0.98476(13) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.1326(3) 0.48035(18) 0.92257(13) 0.0160(3) Uani 1 1 d . . . . .
C3 C -0.0457(3) 0.5480(2) 0.95457(13) 0.0186(3) Uani 1 1 d . . . . .
H3 H -0.145664 0.598565 0.912605 0.022 Uiso 1 1 calc R U . . .
C4 C -0.0755(3) 0.5401(2) 1.05060(14) 0.0213(4) Uani 1 1 d . . . . .
H4 H -0.196300 0.586345 1.074123 0.026 Uiso 1 1 calc R U . . .
C5 C 0.0703(3) 0.4652(2) 1.11163(14) 0.0227(4) Uani 1 1 d . . . . .
H5 H 0.048005 0.461819 1.176479 0.027 Uiso 1 1 calc R U . . .
C6 C 0.2493(3) 0.39463(19) 1.07965(14) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.347378 0.342363 1.121164 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4209(3) 0.38073(19) 0.84284(14) 0.0187(3) Uani 1 1 d . . . . .
C8 C 0.2146(3) 0.47263(18) 0.82627(13) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.2882(3) 0.60451(18) 0.79190(12) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.0780(4) 0.7441(2) 0.68273(15) 0.0245(4) Uani 1 1 d . . . . .
H10A H 0.229629 0.765634 0.663509 0.029 Uiso 1 1 calc R U . . .
H10B H -0.010419 0.825177 0.685530 0.029 Uiso 1 1 calc R U . . .
C11 C -0.0466(3) 0.6499(2) 0.61250(15) 0.0240(4) Uani 1 1 d . . . . .
H11A H -0.188176 0.620250 0.637072 0.029 Uiso 1 1 calc R U . . .
H11B H -0.089882 0.695437 0.552163 0.029 Uiso 1 1 calc R U . . .
C12 C 0.0993(3) 0.5329(2) 0.59475(13) 0.0192(3) Uani 1 1 d . . . . .
C13 C 0.1214(3) 0.4293(2) 0.65288(14) 0.0202(4) Uani 1 1 d . . . . .
H13 H 0.199846 0.356301 0.631906 0.024 Uiso 1 1 calc R U . . .
C14 C 0.0335(3) 0.4184(2) 0.74791(14) 0.0199(4) Uani 1 1 d . . . . .
H14A H 0.001112 0.326580 0.761229 0.024 Uiso 1 1 calc R U . . .
H14B H -0.110111 0.467969 0.747619 0.024 Uiso 1 1 calc R U . . .
C15 C 0.2372(3) 0.5379(2) 0.51330(13) 0.0192(3) Uani 1 1 d . . . . .
C16 C 0.4505(3) 0.4768(2) 0.51893(14) 0.0221(4) Uani 1 1 d . . . . .
H16 H 0.506380 0.432789 0.575216 0.026 Uiso 1 1 calc R U . . .
C17 C 0.5822(3) 0.4792(2) 0.44370(15) 0.0233(4) Uani 1 1 d . . . . .
H17 H 0.725303 0.436282 0.448246 0.028 Uiso 1 1 calc R U . . .
C18 C 0.5016(3) 0.5453(2) 0.36178(13) 0.0218(4) Uani 1 1 d . . . . .
C19 C 0.2951(3) 0.6098(2) 0.35463(15) 0.0255(4) Uani 1 1 d . . . . .
H19 H 0.243075 0.656279 0.298977 0.031 Uiso 1 1 calc R U . . .
C20 C 0.1640(3) 0.6056(2) 0.43030(15) 0.0237(4) Uani 1 1 d . . . . .
H20 H 0.021961 0.649740 0.425461 0.028 Uiso 1 1 calc R U . . .
C22 C 0.6145(3) 0.2554(2) 0.97728(17) 0.0266(4) Uani 1 1 d . . . . .
H22A H 0.703652 0.223042 0.928212 0.040 Uiso 1 1 calc R U . . .
H22B H 0.539497 0.182658 1.005379 0.040 Uiso 1 1 calc R U . . .
H22C H 0.715855 0.299562 1.026120 0.040 Uiso 1 1 calc R U . . .
Cl1 Cl 0.66271(8) 0.54880(5) 0.26713(3) 0.02858(18) Uani 1 1 d . . . . .
N1 N 0.4440(3) 0.34558(17) 0.93613(13) 0.0201(3) Uani 1 1 d . . . . .
O1 O 0.5399(2) 0.34264(17) 0.78427(12) 0.0259(3) Uani 1 1 d . . . . .
O2 O 0.4798(3) 0.63659(16) 0.78073(12) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.1023(3) 0.68067(15) 0.77378(10) 0.0207(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
C1 C2 1.402(2) . ?
C1 C6 1.386(3) . ?
C1 N1 1.404(2) . ?
C2 C3 1.382(2) . ?
C2 C8 1.509(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.542(3) . ?
C7 N1 1.373(3) . ?
C7 O1 1.215(3) . ?
C8 C9 1.526(3) . ?
C8 C14 1.564(2) . ?
C9 O2 1.206(2) . ?
C9 O3 1.352(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.526(3) . ?
C10 O3 1.448(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.521(3) . ?
C12 C13 1.351(3) . ?
C12 C15 1.492(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.509(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.403(3) . ?
C15 C20 1.403(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.393(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.392(3) . ?
C18 C19 1.383(3) . ?
C18 Cl1 1.736(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(3) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 N1 1.448(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 109.89(17) . . ?
C6 C1 C2 122.07(17) . . ?
C6 C1 N1 128.03(17) . . ?
C1 C2 C8 108.28(15) . . ?
C3 C2 C1 120.40(17) . . ?
C3 C2 C8 131.30(16) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.35(17) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.62(17) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.49(18) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.05(17) . . ?
C1 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
N1 C7 C8 107.71(16) . . ?
O1 C7 C8 126.90(19) . . ?
O1 C7 N1 125.36(19) . . ?
C2 C8 C7 102.70(14) . . ?
C2 C8 C9 112.14(15) . . ?
C2 C8 C14 114.08(14) . . ?
C7 C8 C14 110.89(15) . . ?
C9 C8 C7 110.50(14) . . ?
C9 C8 C14 106.58(15) . . ?
O2 C9 C8 126.25(18) . . ?
O2 C9 O3 124.67(18) . . ?
O3 C9 C8 109.07(14) . . ?
H10A C10 H10B 108.5 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
O3 C10 H10A 110.3 . . ?
O3 C10 H10B 110.3 . . ?
O3 C10 C11 107.16(18) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 111.97(16) . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C13 C12 C11 122.99(19) . . ?
C13 C12 C15 118.82(18) . . ?
C15 C12 C11 118.03(17) . . ?
C12 C13 H13 116.9 . . ?
C12 C13 C14 126.27(18) . . ?
C14 C13 H13 116.9 . . ?
C8 C14 H14A 109.7 . . ?
C8 C14 H14B 109.7 . . ?
C13 C14 C8 109.94(15) . . ?
C13 C14 H14A 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C16 C15 C12 120.20(17) . . ?
C16 C15 C20 117.68(17) . . ?
C20 C15 C12 122.10(16) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.39(18) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.21(17) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 Cl1 119.85(15) . . ?
C19 C18 C17 121.04(18) . . ?
C19 C18 Cl1 119.10(16) . . ?
C18 C19 H19 120.4 . . ?
C18 C19 C20 119.14(19) . . ?
C20 C19 H19 120.4 . . ?
C15 C20 H20 119.2 . . ?
C19 C20 C15 121.51(17) . . ?
C19 C20 H20 119.2 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
C1 N1 C22 124.90(18) . . ?
C7 N1 C1 111.40(16) . . ?
C7 N1 C22 123.67(18) . . ?
C9 O3 C10 115.66(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
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C8 C7 0.92(18) . . . . ?
C1 C2 C8 C9 -117.72(16) . . . . ?
C1 C2 C8 C14 120.99(17) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 N1 C7 1.1(2) . . . . ?
C2 C1 N1 C22 -176.75(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C8 C9 O2 112.2(2) . . . . ?
C2 C8 C9 O3 -68.96(18) . . . . ?
C2 C8 C14 C13 173.35(16) . . . . ?
C3 C2 C8 C7 179.46(19) . . . . ?
C3 C2 C8 C9 60.8(2) . . . . ?
C3 C2 C8 C14 -60.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C6 C1 C2 C8 178.27(17) . . . . ?
C6 C1 N1 C7 -178.37(19) . . . . ?
C6 C1 N1 C22 3.7(3) . . . . ?
C7 C8 C9 O2 -1.7(3) . . . . ?
C7 C8 C9 O3 177.12(15) . . . . ?
C7 C8 C14 C13 -71.3(2) . . . . ?
C8 C2 C3 C4 -177.45(19) . . . . ?
C8 C7 N1 C1 -0.5(2) . . . . ?
C8 C7 N1 C22 177.41(17) . . . . ?
C8 C9 O3 C10 -129.89(17) . . . . ?
C9 C8 C14 C13 49.0(2) . . . . ?
C10 C11 C12 C13 81.8(2) . . . . ?
C10 C11 C12 C15 -93.4(2) . . . . ?
C11 C10 O3 C9 86.7(2) . . . . ?
C11 C12 C13 C14 -7.9(3) . . . . ?
C11 C12 C15 C16 145.99(19) . . . . ?
C11 C12 C15 C20 -32.2(3) . . . . ?
C12 C13 C14 C8 -87.5(2) . . . . ?
C12 C15 C16 C17 179.58(19) . . . . ?
C12 C15 C20 C19 179.9(2) . . . . ?
C13 C12 C15 C16 -29.5(3) . . . . ?
C13 C12 C15 C20 152.4(2) . . . . ?
C14 C8 C9 O2 -122.3(2) . . . . ?
C14 C8 C9 O3 56.55(19) . . . . ?
C15 C12 C13 C14 167.32(17) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C15 C20 C19 1.6(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C16 C17 C18 Cl1 -179.71(17) . . . . ?
C17 C18 C19 C20 -1.4(3) . . . . ?
C18 C19 C20 C15 0.1(3) . . . . ?
C20 C15 C16 C17 -2.2(3) . . . . ?
Cl1 C18 C19 C20 179.19(18) . . . . ?
N1 C1 C2 C3 180.00(17) . . . . ?
N1 C1 C2 C8 -1.3(2) . . . . ?
N1 C1 C6 C5 178.92(18) . . . . ?
N1 C7 C8 C2 -0.26(18) . . . . ?
N1 C7 C8 C9 119.52(17) . . . . ?
N1 C7 C8 C14 -122.52(17) . . . . ?
O1 C7 C8 C2 178.01(19) . . . . ?
O1 C7 C8 C9 -62.2(2) . . . . ?
O1 C7 C8 C14 55.8(2) . . . . ?
O1 C7 N1 C1 -178.80(18) . . . . ?
O1 C7 N1 C22 -0.9(3) . . . . ?
O2 C9 O3 C10 49.0(3) . . . . ?
O3 C10 C11 C12 -68.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_250303c_0m
_database_code_depnum_ccdc_archive 'CCDC 2433138'
loop_
_audit_author_name
_audit_author_address
'Yuqing Xiao'
;central china normal university
China
;
_audit_update_record             
;
2025-03-21 deposited with the CCDC.	2025-07-03 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         ?
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.4802(4)
_cell_length_b                   13.0040(6)
_cell_length_c                   17.2546(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.2247(19)
_cell_angle_gamma                90
_cell_volume                     1677.13(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9062
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      72.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.519
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65169
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.229
_diffrn_reflns_theta_max         52.973
_diffrn_reflns_theta_full        52.973
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5849
_reflns_number_gt                5787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.985

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0853P)²+0.7676P] 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       0.078(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2676 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5849
_refine_ls_number_parameters     472
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1306
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_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
C1 C -0.2193(5) 0.7853(3) 0.2808(2) 0.0209(8) Uani 1 1 d . . . . .
C1O C 0.7731(5) 0.3982(3) 0.1356(3) 0.0248(9) Uani 1 1 d . . . . .
H1OA H 0.764357 0.459077 0.168727 0.037 Uiso 1 1 calc R U . . .
H1OB H 0.721309 0.413621 0.083855 0.037 Uiso 1 1 calc R U . . .
H1OC H 0.899065 0.379053 0.131502 0.037 Uiso 1 1 calc R U . . .
C2 C -0.3514(5) 0.8348(3) 0.2353(3) 0.0251(9) Uani 1 1 d . . . . .
H2 H -0.430549 0.882891 0.257248 0.030 Uiso 1 1 calc R U . . .
C3 C -0.3629(5) 0.8113(3) 0.1568(3) 0.0256(9) Uani 1 1 d . . . . .
H3 H -0.452873 0.843298 0.124787 0.031 Uiso 1 1 calc R U . . .
C4 C -0.2465(5) 0.7424(3) 0.1239(2) 0.0252(9) Uani 1 1 d . . . . .
H4 H -0.255847 0.729049 0.069798 0.030 Uiso 1 1 calc R U . . .
C5 C -0.1150(5) 0.6923(3) 0.1702(2) 0.0224(8) Uani 1 1 d . . . . .
H5 H -0.036000 0.644220 0.148039 0.027 Uiso 1 1 calc R U . . .
C6 C -0.1026(5) 0.7145(3) 0.2494(2) 0.0203(8) Uani 1 1 d . . . . .
C7 C 0.0209(5) 0.6750(3) 0.3140(2) 0.0200(8) Uani 1 1 d . . . . .
C8 C -0.0434(5) 0.7324(3) 0.3856(2) 0.0204(8) Uani 1 1 d . . . . .
C9 C -0.2811(6) 0.8594(4) 0.4133(3) 0.0309(10) Uani 1 1 d . . . . .
H9A H -0.278496 0.930802 0.395219 0.046 Uiso 1 1 calc R U . . .
H9B H -0.225946 0.855235 0.465677 0.046 Uiso 1 1 calc R U . . .
H9C H -0.405344 0.835710 0.414220 0.046 Uiso 1 1 calc R U . . .
C10 C 0.0087(5) 0.5559(3) 0.3265(2) 0.0201(8) Uani 1 1 d . . . . .
H10A H -0.110824 0.538194 0.345302 0.024 Uiso 1 1 calc R U . . .
H10B H 0.023366 0.520301 0.276399 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1523(5) 0.5195(3) 0.3849(2) 0.0199(8) Uani 1 1 d . . . . .
H11 H 0.142546 0.548690 0.438188 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3353(5) 0.4886(3) 0.3651(2) 0.0203(8) Uani 1 1 d . . . . .
C13 C 0.3976(5) 0.4839(3) 0.2822(2) 0.0227(8) Uani 1 1 d . . . . .
H13A H 0.302792 0.452164 0.248523 0.027 Uiso 1 1 calc R U . . .
H13B H 0.505426 0.439905 0.280585 0.027 Uiso 1 1 calc R U . . .
C14 C 0.4412(5) 0.5906(3) 0.2511(2) 0.0230(9) Uani 1 1 d . . . . .
H14A H 0.519441 0.628496 0.288880 0.028 Uiso 1 1 calc R U . . .
H14B H 0.503027 0.585019 0.201622 0.028 Uiso 1 1 calc R U . . .
C15 C 0.2159(5) 0.7002(3) 0.2996(2) 0.0195(8) Uani 1 1 d . . . . .
C16 C 0.4830(5) 0.5009(3) 0.4258(2) 0.0218(8) Uani 1 1 d . . . . .
C17 C 0.5939(5) 0.4177(4) 0.4437(3) 0.0268(9) Uani 1 1 d . . . . .
H17 H 0.572885 0.353383 0.418865 0.032 Uiso 1 1 calc R U . . .
C18 C 0.7358(6) 0.4284(4) 0.4979(3) 0.0343(11) Uani 1 1 d . . . . .
H18 H 0.810728 0.371236 0.510224 0.041 Uiso 1 1 calc R U . . .
C19 C 0.7675(6) 0.5227(4) 0.5338(3) 0.0331(11) Uani 1 1 d . . . . .
H19 H 0.864841 0.530143 0.570421 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6577(6) 0.6055(4) 0.5163(3) 0.0306(10) Uani 1 1 d . . . . .
H20 H 0.678824 0.669736 0.541246 0.037 Uiso 1 1 calc R U . . .
C21 C 0.5162(5) 0.5949(3) 0.4624(2) 0.0250(9) Uani 1 1 d . . . . .
H21 H 0.441521 0.652259 0.450278 0.030 Uiso 1 1 calc R U . . .
C22 C 0.7215(5) 0.2678(3) 0.2413(2) 0.0201(8) Uani 1 1 d . . . . .
C23 C 0.8602(5) 0.2935(3) 0.2932(2) 0.0228(8) Uani 1 1 d . . . . .
H23 H 0.940257 0.347938 0.282557 0.027 Uiso 1 1 calc R U . . .
C24 C 0.8781(5) 0.2372(3) 0.3611(2) 0.0238(9) Uani 1 1 d . . . . .
H24 H 0.973101 0.252904 0.397319 0.029 Uiso 1 1 calc R U . . .
C25 C 0.7599(5) 0.1580(3) 0.3775(2) 0.0227(8) Uani 1 1 d . . . . .
H25 H 0.773585 0.121233 0.424936 0.027 Uiso 1 1 calc R U . . .
C26 C 0.6211(5) 0.1325(3) 0.3242(2) 0.0221(8) Uani 1 1 d . . . . .
H26 H 0.540419 0.078353 0.334725 0.026 Uiso 1 1 calc R U . . .
C27 C 0.6037(5) 0.1878(3) 0.2558(2) 0.0188(8) Uani 1 1 d . . . . .
C28 C 0.4722(5) 0.1791(3) 0.1871(2) 0.0191(8) Uani 1 1 d . . . . .
C29 C 0.5286(5) 0.2674(3) 0.1339(2) 0.0201(8) Uani 1 1 d . . . . .
C30 C 0.4859(5) 0.0741(3) 0.1443(2) 0.0193(8) Uani 1 1 d . . . . .
H30A H 0.602877 0.069714 0.119584 0.023 Uiso 1 1 calc R U . . .
H30B H 0.479880 0.017521 0.182542 0.023 Uiso 1 1 calc R U . . .
C31 C 0.3363(5) 0.0612(3) 0.0828(2) 0.0178(8) Uani 1 1 d . . . . .
H31 H 0.338333 0.112572 0.039749 0.021 Uiso 1 1 calc R U . . .
C32 C 0.1560(5) 0.0183(3) 0.0969(2) 0.0201(8) Uani 1 1 d . . . . .
C33 C 0.1053(5) -0.0247(3) 0.1749(2) 0.0214(8) Uani 1 1 d . . . . .
H33A H 0.204729 -0.067790 0.196058 0.026 Uiso 1 1 calc R U . . .
H33B H -0.001101 -0.069381 0.167238 0.026 Uiso 1 1 calc R U . . .
C34 C 0.0643(5) 0.0588(3) 0.2336(2) 0.0229(8) Uani 1 1 d . . . . .
H34A H -0.022599 0.108738 0.210730 0.027 Uiso 1 1 calc R U . . .
H34B H 0.012861 0.028102 0.280274 0.027 Uiso 1 1 calc R U . . .
C35 C 0.2777(5) 0.1905(3) 0.2093(2) 0.0195(8) Uani 1 1 d . . . . .
C36 C 0.0025(5) 0.0544(3) 0.0459(2) 0.0199(8) Uani 1 1 d . . . . .
C37 C -0.0351(5) 0.1586(3) 0.0359(2) 0.0209(8) Uani 1 1 d . . . . .
H37 H 0.041332 0.208422 0.060054 0.025 Uiso 1 1 calc R U . . .
C38 C -0.1837(5) 0.1906(3) -0.0091(2) 0.0221(8) Uani 1 1 d . . . . .
H38 H -0.208306 0.261779 -0.015632 0.027 Uiso 1 1 calc R U . . .
C39 C -0.2951(5) 0.1179(4) -0.0444(2) 0.0238(9) Uani 1 1 d . . . . .
H39 H -0.397173 0.139342 -0.074606 0.029 Uiso 1 1 calc R U . . .
C40 C -0.2584(6) 0.0137(4) -0.0357(2) 0.0284(9) Uani 1 1 d . . . . .
H40 H -0.333943 -0.035984 -0.060582 0.034 Uiso 1 1 calc R U . . .
C41 C -0.1113(5) -0.0174(3) 0.0094(2) 0.0241(9) Uani 1 1 d . . . . .
H41 H -0.087362 -0.088670 0.015762 0.029 Uiso 1 1 calc R U . . .
N1 N -0.1820(4) 0.7946(3) 0.3610(2) 0.0238(7) Uani 1 1 d . . . . .
N2 N 0.6764(4) 0.3139(2) 0.16913(19) 0.0202(7) Uani 1 1 d . . . . .
O1 O 0.0151(4) 0.7234(2) 0.45149(16) 0.0246(6) Uani 1 1 d . . . . .
O2 O 0.2014(4) 0.4121(2) 0.38292(17) 0.0235(6) Uani 1 1 d . . . . .
O3 O 0.2712(3) 0.6433(2) 0.23933(16) 0.0212(6) Uani 1 1 d . . . . .
O4 O 0.3080(4) 0.7584(2) 0.33644(17) 0.0263(6) Uani 1 1 d . . . . .
O5 O 0.4610(4) 0.2904(2) 0.07114(17) 0.0263(6) Uani 1 1 d . . . . .
O6 O 0.2909(3) -0.0418(2) 0.05813(16) 0.0223(6) Uani 1 1 d . . . . .
O7 O 0.2326(3) 0.1095(2) 0.25388(16) 0.0208(6) Uani 1 1 d . . . . .
O8 O 0.1772(3) 0.2575(2) 0.18769(17) 0.0238(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.392(5) . ?
C1 C2 1.396(6) . ?
C1 N1 1.405(5) . ?
C1O N2 1.447(5) . ?
C1O H1OA 0.9800 . ?
C1O H1OB 0.9800 . ?
C1O H1OC 0.9800 . ?
C2 C3 1.388(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.510(5) . ?
C7 C15 1.525(5) . ?
C7 C8 1.538(5) . ?
C7 C10 1.566(5) . ?
C8 O1 1.208(5) . ?
C8 N1 1.370(5) . ?
C9 N1 1.458(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.520(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 O2 1.445(5) . ?
C11 C12 1.479(5) . ?
C11 H11 1.0000 . ?
C12 O2 1.453(5) . ?
C12 C16 1.501(5) . ?
C12 C13 1.522(6) . ?
C13 C14 1.527(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O3 1.452(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O4 1.191(5) . ?
C15 O3 1.354(5) . ?
C16 C17 1.391(6) . ?
C16 C21 1.394(6) . ?
C17 C18 1.394(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.385(6) . ?
C22 C27 1.392(5) . ?
C22 N2 1.411(5) . ?
C23 C24 1.383(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.394(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.400(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.383(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.515(5) . ?
C28 C35 1.526(5) . ?
C28 C29 1.540(5) . ?
C28 C30 1.557(5) . ?
C29 O5 1.214(5) . ?
C29 N2 1.380(5) . ?
C30 C31 1.522(5) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 O6 1.442(5) . ?
C31 C32 1.487(5) . ?
C31 H31 1.0000 . ?
C32 O6 1.459(5) . ?
C32 C36 1.495(5) . ?
C32 C33 1.519(6) . ?
C33 C34 1.524(6) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O7 1.452(4) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 O8 1.201(5) . ?
C35 O7 1.354(5) . ?
C36 C37 1.393(6) . ?
C36 C41 1.396(5) . ?
C37 C38 1.394(6) . ?
C37 H37 0.9500 . ?
C38 C39 1.385(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.389(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.383(6) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?

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 C1 C2 121.7(4) . . ?
C6 C1 N1 109.7(3) . . ?
C2 C1 N1 128.5(4) . . ?
N2 C1O H1OA 109.5 . . ?
N2 C1O H1OB 109.5 . . ?
H1OA C1O H1OB 109.5 . . ?
N2 C1O H1OC 109.5 . . ?
H1OA C1O H1OC 109.5 . . ?
H1OB C1O H1OC 109.5 . . ?
C3 C2 C1 117.6(4) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 C7 108.2(3) . . ?
C5 C6 C7 131.8(4) . . ?
C6 C7 C15 111.6(3) . . ?
C6 C7 C8 103.1(3) . . ?
C15 C7 C8 110.9(3) . . ?
C6 C7 C10 113.6(3) . . ?
C15 C7 C10 107.3(3) . . ?
C8 C7 C10 110.4(3) . . ?
O1 C8 N1 126.3(4) . . ?
O1 C8 C7 126.6(4) . . ?
N1 C8 C7 107.1(3) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 110.8(3) . . ?
C11 C10 H10A 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 C12 59.6(2) . . ?
O2 C11 C10 117.3(3) . . ?
C12 C11 C10 124.6(3) . . ?
O2 C11 H11 114.6 . . ?
C12 C11 H11 114.6 . . ?
C10 C11 H11 114.6 . . ?
O2 C12 C11 59.0(2) . . ?
O2 C12 C16 114.8(3) . . ?
C11 C12 C16 118.2(3) . . ?
O2 C12 C13 114.2(3) . . ?
C11 C12 C13 123.2(3) . . ?
C16 C12 C13 114.5(3) . . ?
C12 C13 C14 111.8(3) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O3 C14 C13 106.3(3) . . ?
O3 C14 H14A 110.5 . . ?
C13 C14 H14A 110.5 . . ?
O3 C14 H14B 110.5 . . ?
C13 C14 H14B 110.5 . . ?
H14A C14 H14B 108.7 . . ?
O4 C15 O3 124.7(4) . . ?
O4 C15 C7 126.0(4) . . ?
O3 C15 C7 109.3(3) . . ?
C17 C16 C21 119.2(4) . . ?
C17 C16 C12 119.3(4) . . ?
C21 C16 C12 121.5(4) . . ?
C16 C17 C18 120.2(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.0(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.1(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C16 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C23 C22 C27 121.8(4) . . ?
C23 C22 N2 128.0(4) . . ?
C27 C22 N2 110.2(3) . . ?
C24 C23 C22 117.8(4) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C23 C24 C25 121.4(4) . . ?
C23 C24 H24 119.3 . . ?
C25 C24 H24 119.3 . . ?
C24 C25 C26 120.1(4) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C27 C26 C25 118.7(4) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C22 120.2(4) . . ?
C26 C27 C28 131.7(4) . . ?
C22 C27 C28 108.1(3) . . ?
C27 C28 C35 113.1(3) . . ?
C27 C28 C29 103.1(3) . . ?
C35 C28 C29 111.3(3) . . ?
C27 C28 C30 112.5(3) . . ?
C35 C28 C30 106.6(3) . . ?
C29 C28 C30 110.3(3) . . ?
O5 C29 N2 125.7(4) . . ?
O5 C29 C28 127.0(3) . . ?
N2 C29 C28 107.3(3) . . ?
C31 C30 C28 111.5(3) . . ?
C31 C30 H30A 109.3 . . ?
C28 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
C28 C30 H30B 109.3 . . ?
H30A C30 H30B 108.0 . . ?
O6 C31 C32 59.7(2) . . ?
O6 C31 C30 117.8(3) . . ?
C32 C31 C30 125.0(3) . . ?
O6 C31 H31 114.3 . . ?
C32 C31 H31 114.3 . . ?
C30 C31 H31 114.3 . . ?
O6 C32 C31 58.6(2) . . ?
O6 C32 C36 115.3(3) . . ?
C31 C32 C36 117.8(3) . . ?
O6 C32 C33 114.2(3) . . ?
C31 C32 C33 122.8(3) . . ?
C36 C32 C33 115.1(3) . . ?
C32 C33 C34 113.0(3) . . ?
C32 C33 H33A 109.0 . . ?
C34 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
C34 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
O7 C34 C33 106.8(3) . . ?
O7 C34 H34A 110.4 . . ?
C33 C34 H34A 110.4 . . ?
O7 C34 H34B 110.4 . . ?
C33 C34 H34B 110.4 . . ?
H34A C34 H34B 108.6 . . ?
O8 C35 O7 125.0(3) . . ?
O8 C35 C28 125.7(4) . . ?
O7 C35 C28 109.2(3) . . ?
C37 C36 C41 118.5(4) . . ?
C37 C36 C32 121.6(3) . . ?
C41 C36 C32 119.8(4) . . ?
C36 C37 C38 120.8(4) . . ?
C36 C37 H37 119.6 . . ?
C38 C37 H37 119.6 . . ?
C39 C38 C37 119.6(4) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 120.3(4) . . ?
C38 C39 H39 119.8 . . ?
C40 C39 H39 119.8 . . ?
C41 C40 C39 119.7(4) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C40 C41 C36 121.1(4) . . ?
C40 C41 H41 119.5 . . ?
C36 C41 H41 119.5 . . ?
C8 N1 C1 111.9(3) . . ?
C8 N1 C9 123.1(4) . . ?
C1 N1 C9 125.0(3) . . ?
C29 N2 C22 111.3(3) . . ?
C29 N2 C1O 124.1(3) . . ?
C22 N2 C1O 124.7(3) . . ?
C11 O2 C12 61.4(2) . . ?
C15 O3 C14 116.2(3) . . ?
C31 O6 C32 61.7(2) . . ?
C35 O7 C34 116.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(6) . . . . ?
N1 C1 C2 C3 -179.1(4) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 1.5(6) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
N1 C1 C6 C5 179.8(4) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
N1 C1 C6 C7 -0.2(4) . . . . ?
C4 C5 C6 C1 -0.1(6) . . . . ?
C4 C5 C6 C7 180.0(4) . . . . ?
C1 C6 C7 C15 -118.7(3) . . . . ?
C5 C6 C7 C15 61.3(5) . . . . ?
C1 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C8 -179.6(4) . . . . ?
C1 C6 C7 C10 119.9(4) . . . . ?
C5 C6 C7 C10 -60.2(5) . . . . ?
C6 C7 C8 O1 178.5(4) . . . . ?
C15 C7 C8 O1 -61.9(5) . . . . ?
C10 C7 C8 O1 56.8(5) . . . . ?
C6 C7 C8 N1 -0.4(4) . . . . ?
C15 C7 C8 N1 119.1(3) . . . . ?
C10 C7 C8 N1 -122.1(3) . . . . ?
C6 C7 C10 C11 172.8(3) . . . . ?
C15 C7 C10 C11 49.0(4) . . . . ?
C8 C7 C10 C11 -72.0(4) . . . . ?
C7 C10 C11 O2 -158.5(3) . . . . ?
C7 C10 C11 C12 -88.2(4) . . . . ?
C10 C11 C12 O2 -104.0(4) . . . . ?
O2 C11 C12 C16 -103.5(4) . . . . ?
C10 C11 C12 C16 152.5(4) . . . . ?
O2 C11 C12 C13 100.3(4) . . . . ?
C10 C11 C12 C13 -3.7(6) . . . . ?
O2 C12 C13 C14 146.0(3) . . . . ?
C11 C12 C13 C14 78.3(5) . . . . ?
C16 C12 C13 C14 -78.6(4) . . . . ?
C12 C13 C14 O3 -71.0(4) . . . . ?
C6 C7 C15 O4 112.3(4) . . . . ?
C8 C7 C15 O4 -2.0(5) . . . . ?
C10 C7 C15 O4 -122.6(4) . . . . ?
C6 C7 C15 O3 -69.6(4) . . . . ?
C8 C7 C15 O3 176.1(3) . . . . ?
C10 C7 C15 O3 55.5(4) . . . . ?
O2 C12 C16 C17 61.7(5) . . . . ?
C11 C12 C16 C17 128.5(4) . . . . ?
C13 C12 C16 C17 -73.3(5) . . . . ?
O2 C12 C16 C21 -120.9(4) . . . . ?
C11 C12 C16 C21 -54.2(5) . . . . ?
C13 C12 C16 C21 104.0(4) . . . . ?
C21 C16 C17 C18 0.4(6) . . . . ?
C12 C16 C17 C18 177.8(4) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C17 C18 C19 C20 0.6(7) . . . . ?
C18 C19 C20 C21 -0.5(7) . . . . ?
C19 C20 C21 C16 0.4(6) . . . . ?
C17 C16 C21 C20 -0.3(6) . . . . ?
C12 C16 C21 C20 -177.7(4) . . . . ?
C27 C22 C23 C24 -0.5(5) . . . . ?
N2 C22 C23 C24 179.8(4) . . . . ?
C22 C23 C24 C25 -0.7(6) . . . . ?
C23 C24 C25 C26 1.2(6) . . . . ?
C24 C25 C26 C27 -0.4(6) . . . . ?
C25 C26 C27 C22 -0.8(6) . . . . ?
C25 C26 C27 C28 179.3(4) . . . . ?
C23 C22 C27 C26 1.2(6) . . . . ?
N2 C22 C27 C26 -179.0(3) . . . . ?
C23 C22 C27 C28 -178.8(3) . . . . ?
N2 C22 C27 C28 1.0(4) . . . . ?
C26 C27 C28 C35 57.8(5) . . . . ?
C22 C27 C28 C35 -122.2(4) . . . . ?
C26 C27 C28 C29 178.1(4) . . . . ?
C22 C27 C28 C29 -1.9(4) . . . . ?
C26 C27 C28 C30 -63.1(5) . . . . ?
C22 C27 C28 C30 116.9(3) . . . . ?
C27 C28 C29 O5 179.7(4) . . . . ?
C35 C28 C29 O5 -58.8(5) . . . . ?
C30 C28 C29 O5 59.3(5) . . . . ?
C27 C28 C29 N2 2.2(4) . . . . ?
C35 C28 C29 N2 123.7(3) . . . . ?
C30 C28 C29 N2 -118.2(3) . . . . ?
C27 C28 C30 C31 172.2(3) . . . . ?
C35 C28 C30 C31 47.6(4) . . . . ?
C29 C28 C30 C31 -73.4(4) . . . . ?
C28 C30 C31 O6 -158.2(3) . . . . ?
C28 C30 C31 C32 -87.2(4) . . . . ?
C30 C31 C32 O6 -104.5(4) . . . . ?
O6 C31 C32 C36 -104.1(4) . . . . ?
C30 C31 C32 C36 151.3(4) . . . . ?
O6 C31 C32 C33 100.2(4) . . . . ?
C30 C31 C32 C33 -4.3(6) . . . . ?
O6 C32 C33 C34 144.9(3) . . . . ?
C31 C32 C33 C34 77.9(4) . . . . ?
C36 C32 C33 C34 -78.4(4) . . . . ?
C32 C33 C34 O7 -69.4(4) . . . . ?
C27 C28 C35 O8 117.0(4) . . . . ?
C29 C28 C35 O8 1.5(5) . . . . ?
C30 C28 C35 O8 -118.8(4) . . . . ?
C27 C28 C35 O7 -66.5(4) . . . . ?
C29 C28 C35 O7 178.0(3) . . . . ?
C30 C28 C35 O7 57.7(4) . . . . ?
O6 C32 C36 C37 -119.6(4) . . . . ?
C31 C32 C36 C37 -53.4(5) . . . . ?
C33 C32 C36 C37 104.2(4) . . . . ?
O6 C32 C36 C41 63.0(5) . . . . ?
C31 C32 C36 C41 129.3(4) . . . . ?
C33 C32 C36 C41 -73.2(4) . . . . ?
C41 C36 C37 C38 0.3(6) . . . . ?
C32 C36 C37 C38 -177.1(3) . . . . ?
C36 C37 C38 C39 0.0(6) . . . . ?
C37 C38 C39 C40 -0.7(6) . . . . ?
C38 C39 C40 C41 1.0(6) . . . . ?
C39 C40 C41 C36 -0.7(6) . . . . ?
C37 C36 C41 C40 0.1(6) . . . . ?
C32 C36 C41 C40 177.5(4) . . . . ?
O1 C8 N1 C1 -178.6(4) . . . . ?
C7 C8 N1 C1 0.3(4) . . . . ?
O1 C8 N1 C9 -0.6(6) . . . . ?
C7 C8 N1 C9 178.3(4) . . . . ?
C6 C1 N1 C8 0.0(4) . . . . ?
C2 C1 N1 C8 179.1(4) . . . . ?
C6 C1 N1 C9 -178.0(4) . . . . ?
C2 C1 N1 C9 1.1(6) . . . . ?
O5 C29 N2 C22 -179.3(4) . . . . ?
C28 C29 N2 C22 -1.7(4) . . . . ?
O5 C29 N2 C1O 0.1(6) . . . . ?
C28 C29 N2 C1O 177.7(3) . . . . ?
C23 C22 N2 C29 -179.8(4) . . . . ?
C27 C22 N2 C29 0.5(4) . . . . ?
C23 C22 N2 C1O 0.9(6) . . . . ?
C27 C22 N2 C1O -178.9(3) . . . . ?
C10 C11 O2 C12 116.0(4) . . . . ?
C16 C12 O2 C11 109.3(4) . . . . ?
C13 C12 O2 C11 -115.5(4) . . . . ?
O4 C15 O3 C14 46.0(5) . . . . ?
C7 C15 O3 C14 -132.1(3) . . . . ?
C13 C14 O3 C15 91.8(4) . . . . ?
C30 C31 O6 C32 116.3(4) . . . . ?
C36 C32 O6 C31 108.4(4) . . . . ?
C33 C32 O6 C31 -114.9(4) . . . . ?
O8 C35 O7 C34 43.7(5) . . . . ?
C28 C35 O7 C34 -132.8(3) . . . . ?
C33 C34 O7 C35 89.0(4) . . . . ?

_refine_diff_density_max         0.938
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.178



####################################################################### 
# 
# 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_250219a_liyujie_0m
_database_code_depnum_ccdc_archive 'CCDC 2433137'
loop_
_audit_author_name
_audit_author_address
'Yuqing Xiao'
;central china normal university
China
;
_audit_update_record             
;
2025-03-21 deposited with the CCDC.	2025-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O3'
_chemical_formula_weight         335.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.7817(4)
_cell_length_b                   8.2331(5)
_cell_length_c                   31.286(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1746.82(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      4.83
_cell_measurement_theta_max      73.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.436
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6462
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73442
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         4.832
_diffrn_reflns_theta_max         73.471
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5330
_reflns_number_gt                5172
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0574P)²+1.4690P] 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-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0065(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2063 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5330
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5554(4) 0.2777(3) 0.41921(8) 0.0120(4) Uani 1 1 d . . . . .
C2 C 0.5466(4) 0.4645(3) 0.42344(7) 0.0099(4) Uani 1 1 d . . . . .
C3 C 0.5440(3) 0.4881(3) 0.47154(7) 0.0093(4) Uani 1 1 d . . . . .
C4 C 0.5437(4) 0.3353(3) 0.49107(7) 0.0096(4) Uani 1 1 d . . . . .
C5 C 0.5405(4) 0.3170(3) 0.53520(8) 0.0132(4) Uani 1 1 d . . . . .
H5 H 0.537646 0.212469 0.548056 0.016 Uiso 1 1 calc R U . . .
C6 C 0.5417(4) 0.4586(3) 0.55999(8) 0.0145(5) Uani 1 1 d . . . . .
H6 H 0.541374 0.450197 0.590272 0.017 Uiso 1 1 calc R U . . .
C7 C 0.5435(4) 0.6118(3) 0.54097(8) 0.0148(5) Uani 1 1 d . . . . .
H7 H 0.543987 0.706356 0.558386 0.018 Uiso 1 1 calc R U . . .
C8 C 0.5444(4) 0.6274(3) 0.49641(8) 0.0121(4) Uani 1 1 d . . . . .
H8 H 0.545353 0.731738 0.483433 0.014 Uiso 1 1 calc R U . . .
C9 C 0.5448(4) 0.0409(3) 0.46914(8) 0.0143(4) Uani 1 1 d . . . . .
H9A H 0.662325 0.012833 0.485811 0.021 Uiso 1 1 calc R U . . .
H9B H 0.544838 -0.020593 0.442330 0.021 Uiso 1 1 calc R U . . .
H9C H 0.426352 0.014006 0.485620 0.021 Uiso 1 1 calc R U . . .
C10 C 0.3608(3) 0.5344(3) 0.40094(8) 0.0134(5) Uani 1 1 d . . . . .
H10A H 0.246645 0.465723 0.408830 0.016 Uiso 1 1 calc R U . . .
H10B H 0.335928 0.644269 0.412632 0.016 Uiso 1 1 calc R U . . .
C11 C 0.3668(4) 0.5475(3) 0.35171(8) 0.0139(5) Uani 1 1 d . . . . .
H11A H 0.231992 0.526997 0.340850 0.017 Uiso 1 1 calc R U . . .
H11B H 0.451881 0.458900 0.340864 0.017 Uiso 1 1 calc R U . . .
C12 C 0.4411(4) 0.7101(3) 0.33162(7) 0.0122(4) Uani 1 1 d . . . . .
H12 H 0.398637 0.800805 0.350783 0.015 Uiso 1 1 calc R U . . .
C13 C 0.6686(4) 0.7230(3) 0.32567(8) 0.0152(5) Uani 1 1 d . . . . .
H13A H 0.721359 0.614121 0.318604 0.018 Uiso 1 1 calc R U . . .
H13B H 0.696536 0.795535 0.301175 0.018 Uiso 1 1 calc R U . . .
C14 C 0.7753(4) 0.7873(4) 0.36490(8) 0.0164(5) Uani 1 1 d . . . . .
H14A H 0.918573 0.766369 0.362335 0.020 Uiso 1 1 calc R U . . .
H14B H 0.755039 0.906018 0.367382 0.020 Uiso 1 1 calc R U . . .
C15 C 0.7285(3) 0.5441(3) 0.40424(8) 0.0125(5) Uani 1 1 d . . . . .
C16 C 0.3408(4) 0.7341(3) 0.28845(8) 0.0148(5) Uani 1 1 d . . . . .
C17 C 0.4005(5) 0.6446(4) 0.25273(9) 0.0218(6) Uani 1 1 d . . . . .
H17 H 0.502292 0.565960 0.255408 0.026 Uiso 1 1 calc R U . . .
C18 C 0.3107(6) 0.6707(4) 0.21307(10) 0.0289(7) Uani 1 1 d . . . . .
H18 H 0.354059 0.611396 0.188770 0.035 Uiso 1 1 calc R U . . .
C19 C 0.1593(5) 0.7819(5) 0.20896(10) 0.0314(7) Uani 1 1 d . . . . .
H19 H 0.098275 0.798400 0.181969 0.038 Uiso 1 1 calc R U . . .
C20 C 0.0964(5) 0.8699(5) 0.24442(11) 0.0299(7) Uani 1 1 d . . . . .
H20 H -0.008650 0.945576 0.241851 0.036 Uiso 1 1 calc R U . . .
C21 C 0.1890(4) 0.8460(4) 0.28389(9) 0.0218(6) Uani 1 1 d . . . . .
H21 H 0.147323 0.907370 0.307964 0.026 Uiso 1 1 calc R U . . .
N1 N 0.5462(3) 0.2132(2) 0.45979(6) 0.0103(4) Uani 1 1 d . . . . .
O1 O 0.6975(3) 0.7058(2) 0.40259(6) 0.0138(4) Uani 1 1 d . . . . .
O2 O 0.8748(3) 0.4769(3) 0.39184(6) 0.0202(4) Uani 1 1 d . . . . .
O3 O 0.5609(4) 0.1993(3) 0.38638(6) 0.0221(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O3 1.214(3) . ?
C1 N1 1.378(3) . ?
C1 C2 1.545(3) . ?
C2 C3 1.517(3) . ?
C2 C15 1.521(3) . ?
C2 C10 1.554(3) . ?
C3 C8 1.386(3) . ?
C3 C4 1.399(3) . ?
C4 C5 1.389(3) . ?
C4 N1 1.403(3) . ?
C5 C6 1.401(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.400(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 N1 1.448(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.545(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.562(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.525(3) . ?
C12 C13 1.558(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.520(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O1 1.456(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 O2 1.200(3) . ?
C15 O1 1.349(3) . ?
C16 C21 1.389(4) . ?
C16 C17 1.399(4) . ?
C17 C18 1.399(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

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
O3 C1 N1 125.2(2) . . ?
O3 C1 C2 127.1(2) . . ?
N1 C1 C2 107.6(2) . . ?
C3 C2 C15 110.24(19) . . ?
C3 C2 C1 102.31(18) . . ?
C15 C2 C1 111.4(2) . . ?
C3 C2 C10 113.07(19) . . ?
C15 C2 C10 108.59(18) . . ?
C1 C2 C10 111.2(2) . . ?
C8 C3 C4 119.9(2) . . ?
C8 C3 C2 131.5(2) . . ?
C4 C3 C2 108.5(2) . . ?
C5 C4 C3 122.1(2) . . ?
C5 C4 N1 128.0(2) . . ?
C3 C4 N1 109.9(2) . . ?
C4 C5 C6 117.4(2) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 118.9(2) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C2 117.1(2) . . ?
C11 C10 H10A 108.0 . . ?
C2 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
C2 C10 H10B 108.0 . . ?
H10A C10 H10B 107.3 . . ?
C10 C11 C12 118.0(2) . . ?
C10 C11 H11A 107.8 . . ?
C12 C11 H11A 107.8 . . ?
C10 C11 H11B 107.8 . . ?
C12 C11 H11B 107.8 . . ?
H11A C11 H11B 107.1 . . ?
C16 C12 C13 109.1(2) . . ?
C16 C12 C11 108.9(2) . . ?
C13 C12 C11 115.2(2) . . ?
C16 C12 H12 107.8 . . ?
C13 C12 H12 107.8 . . ?
C11 C12 H12 107.8 . . ?
C14 C13 C12 113.5(2) . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
O1 C14 C13 108.7(2) . . ?
O1 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
O1 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O2 C15 O1 124.9(2) . . ?
O2 C15 C2 126.8(3) . . ?
O1 C15 C2 108.3(2) . . ?
C21 C16 C17 118.8(3) . . ?
C21 C16 C12 120.5(2) . . ?
C17 C16 C12 120.7(2) . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C16 C21 C20 121.1(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C1 N1 C4 111.5(2) . . ?
C1 N1 C9 124.3(2) . . ?
C4 N1 C9 124.1(2) . . ?
C15 O1 C14 115.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C2 C3 -179.7(3) . . . . ?
N1 C1 C2 C3 3.2(3) . . . . ?
O3 C1 C2 C15 -61.9(3) . . . . ?
N1 C1 C2 C15 121.0(2) . . . . ?
O3 C1 C2 C10 59.3(3) . . . . ?
N1 C1 C2 C10 -117.8(2) . . . . ?
C15 C2 C3 C8 58.6(3) . . . . ?
C1 C2 C3 C8 177.1(3) . . . . ?
C10 C2 C3 C8 -63.2(3) . . . . ?
C15 C2 C3 C4 -120.5(2) . . . . ?
C1 C2 C3 C4 -2.0(3) . . . . ?
C10 C2 C3 C4 117.7(2) . . . . ?
C8 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C4 C5 -179.7(2) . . . . ?
C8 C3 C4 N1 -179.1(2) . . . . ?
C2 C3 C4 N1 0.1(3) . . . . ?
C3 C4 C5 C6 -1.3(4) . . . . ?
N1 C4 C5 C6 179.0(2) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C4 C3 C8 C7 -0.3(4) . . . . ?
C2 C3 C8 C7 -179.4(2) . . . . ?
C6 C7 C8 C3 -0.1(4) . . . . ?
C3 C2 C10 C11 168.2(2) . . . . ?
C15 C2 C10 C11 45.5(3) . . . . ?
C1 C2 C10 C11 -77.3(3) . . . . ?
C2 C10 C11 C12 -91.8(3) . . . . ?
C10 C11 C12 C16 -150.7(2) . . . . ?
C10 C11 C12 C13 86.4(3) . . . . ?
C16 C12 C13 C14 150.2(2) . . . . ?
C11 C12 C13 C14 -87.1(3) . . . . ?
C12 C13 C14 O1 44.9(3) . . . . ?
C3 C2 C15 O2 104.0(3) . . . . ?
C1 C2 C15 O2 -8.8(3) . . . . ?
C10 C2 C15 O2 -131.6(3) . . . . ?
C3 C2 C15 O1 -77.0(2) . . . . ?
C1 C2 C15 O1 170.10(19) . . . . ?
C10 C2 C15 O1 47.3(2) . . . . ?
C13 C12 C16 C21 -128.9(3) . . . . ?
C11 C12 C16 C21 104.7(3) . . . . ?
C13 C12 C16 C17 50.9(3) . . . . ?
C11 C12 C16 C17 -75.6(3) . . . . ?
C21 C16 C17 C18 1.3(4) . . . . ?
C12 C16 C17 C18 -178.4(3) . . . . ?
C16 C17 C18 C19 -1.5(5) . . . . ?
C17 C18 C19 C20 0.5(5) . . . . ?
C18 C19 C20 C21 0.8(5) . . . . ?
C17 C16 C21 C20 0.0(4) . . . . ?
C12 C16 C21 C20 179.7(3) . . . . ?
C19 C20 C21 C16 -1.0(5) . . . . ?
O3 C1 N1 C4 179.4(3) . . . . ?
C2 C1 N1 C4 -3.4(3) . . . . ?
O3 C1 N1 C9 1.0(4) . . . . ?
C2 C1 N1 C9 178.2(2) . . . . ?
C5 C4 N1 C1 -178.1(2) . . . . ?
C3 C4 N1 C1 2.1(3) . . . . ?
C5 C4 N1 C9 0.4(4) . . . . ?
C3 C4 N1 C9 -179.4(2) . . . . ?
O2 C15 O1 C14 36.7(3) . . . . ?
C2 C15 O1 C14 -142.2(2) . . . . ?
C13 C14 O1 C15 63.9(3) . . . . ?

_refine_diff_density_max         0.519
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.074



