# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_cxy6053_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2p596d
_database_code_depnum_ccdc_archive 'CCDC 2477743'
loop_
_audit_author_name
_audit_author_address
'zhuang haokun'
;Shenzhen University of Science and Technology
China
;
_audit_update_record             
;
2025-08-01 deposited with the CCDC.	2026-01-18 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O'
_chemical_formula_sum            'C17 H15 N O'
_chemical_formula_weight         249.30
_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'
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                   5.7891(7)
_cell_length_b                   7.6847(9)
_cell_length_c                   14.5137(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.419(6)
_cell_angle_gamma                90
_cell_volume                     644.53(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9785
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      57.10
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1296 before and 0.0893 after correction.
The Ratio of minimum to maximum transmission is 0.8247.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28978
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.101
_diffrn_reflns_theta_min         5.312
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           3.0
_diffrn_source_power             0.20958
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.843
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2506
_reflns_number_total             2630
_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 (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT 2014'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.078
_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)+(0.0430P)²+0.1395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
O1 O 0.6262(3) 0.6826(2) 0.77827(10) 0.0339(4) Uani 1 1 d . . . . .
H1 H 0.660627 0.698267 0.723467 0.051 Uiso 1 1 calc R U . . .
N1 N 0.4275(3) 0.6433(2) 0.61558(12) 0.0258(4) Uani 1 1 d . . . . .
C1 C 0.2126(4) 0.5574(3) 0.34001(15) 0.0328(5) Uani 1 1 d . . . . .
H1A H 0.166607 0.538864 0.276844 0.039 Uiso 1 1 calc R U . . .
C2 C 0.4291(4) 0.6357(3) 0.36433(15) 0.0318(5) Uani 1 1 d . . . . .
H2 H 0.527787 0.669094 0.317407 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4970(4) 0.6635(3) 0.45507(14) 0.0286(5) Uani 1 1 d . . . . .
H3 H 0.642497 0.716293 0.470640 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3533(4) 0.6144(2) 0.52561(14) 0.0250(4) Uani 1 1 d . . . . .
C5 C 0.2937(4) 0.5968(3) 0.68129(14) 0.0253(4) Uani 1 1 d . . . . .
C6 C 0.3866(4) 0.6415(3) 0.77987(14) 0.0275(4) Uani 1 1 d . . . . .
C7 C 0.3610(4) 0.4863(3) 0.84419(13) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.5340(4) 0.3594(3) 0.85107(15) 0.0315(5) Uani 1 1 d . . . . .
H8 H 0.666070 0.370349 0.815676 0.038 Uiso 1 1 calc R U . . .
C9 C 0.5145(4) 0.2171(3) 0.90927(17) 0.0384(5) Uani 1 1 d . . . . .
H9 H 0.632916 0.131421 0.913205 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3241(5) 0.1997(3) 0.96134(16) 0.0407(6) Uani 1 1 d . . . . .
H10 H 0.312504 0.103196 1.001729 0.049 Uiso 1 1 calc R U . . .
C11 C 0.0743(4) 0.5168(3) 0.66343(14) 0.0285(5) Uani 1 1 d . . . . .
H11 H -0.017227 0.484432 0.712867 0.034 Uiso 1 1 calc R U . . .
C12 C -0.0026(4) 0.4872(3) 0.57440(14) 0.0281(4) Uani 1 1 d . . . . .
H12 H -0.148910 0.433901 0.561210 0.034 Uiso 1 1 calc R U . . .
C13 C 0.1355(4) 0.5358(3) 0.50157(14) 0.0259(4) Uani 1 1 d . . . . .
C14 C 0.0694(4) 0.5083(3) 0.40691(14) 0.0301(5) Uani 1 1 d . . . . .
H14 H -0.075348 0.455513 0.389966 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2577(4) 0.8028(3) 0.81192(16) 0.0348(5) Uani 1 1 d . . . . .
H15A H 0.307311 0.828807 0.876188 0.052 Uiso 1 1 calc R U . . .
H15B H 0.090772 0.780464 0.807245 0.052 Uiso 1 1 calc R U . . .
H15C H 0.292690 0.902213 0.772819 0.052 Uiso 1 1 calc R U . . .
C16 C 0.1503(5) 0.3231(4) 0.95451(16) 0.0399(6) Uani 1 1 d . . . . .
H16 H 0.018034 0.310711 0.989705 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1687(4) 0.4657(3) 0.89606(15) 0.0328(5) Uani 1 1 d . . . . .
H17 H 0.048335 0.549907 0.891627 0.039 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C6 1.424(3) . ?
N1 C4 1.368(3) . ?
N1 C5 1.314(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.416(3) . ?
C1 C14 1.367(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(3) . ?
C4 C13 1.422(3) . ?
C5 C6 1.537(3) . ?
C5 C11 1.421(3) . ?
C6 C7 1.527(3) . ?
C6 C15 1.533(3) . ?
C7 C8 1.397(3) . ?
C7 C17 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(4) . ?
C10 H10 0.9500 . ?
C10 C16 1.382(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.360(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.413(3) . ?
C13 C14 1.420(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C17 1.394(3) . ?
C17 H17 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 O1 H1 109.5 . . ?
C5 N1 C4 118.92(18) . . ?
C2 C1 H1A 119.8 . . ?
C14 C1 H1A 119.8 . . ?
C14 C1 C2 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
N1 C4 C3 119.00(18) . . ?
N1 C4 C13 121.75(18) . . ?
C3 C4 C13 119.25(18) . . ?
N1 C5 C6 115.20(18) . . ?
N1 C5 C11 123.01(18) . . ?
C11 C5 C6 121.75(18) . . ?
O1 C6 C5 108.76(16) . . ?
O1 C6 C7 108.26(17) . . ?
O1 C6 C15 108.55(18) . . ?
C7 C6 C5 110.65(17) . . ?
C7 C6 C15 112.28(17) . . ?
C15 C6 C5 108.27(17) . . ?
C8 C7 C6 119.58(19) . . ?
C17 C7 C6 122.00(19) . . ?
C17 C7 C8 118.4(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C16 119.7(2) . . ?
C16 C10 H10 120.1 . . ?
C5 C11 H11 120.5 . . ?
C12 C11 C5 118.93(18) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.90(19) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C4 117.49(18) . . ?
C12 C13 C14 123.5(2) . . ?
C14 C13 C4 118.98(19) . . ?
C1 C14 C13 120.4(2) . . ?
C1 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16 120.0 . . ?
C10 C16 C17 120.1(2) . . ?
C17 C16 H16 120.0 . . ?
C7 C17 C16 120.8(2) . . ?
C7 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?

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
O1 C6 C7 C8 -32.9(2) . . . . ?
O1 C6 C7 C17 147.69(19) . . . . ?
N1 C4 C13 C12 -0.3(3) . . . . ?
N1 C4 C13 C14 -179.56(19) . . . . ?
N1 C5 C6 O1 -15.3(2) . . . . ?
N1 C5 C6 C7 -134.10(18) . . . . ?
N1 C5 C6 C15 102.5(2) . . . . ?
N1 C5 C11 C12 -0.3(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C1 C14 C13 0.2(3) . . . . ?
C2 C3 C4 N1 179.62(18) . . . . ?
C2 C3 C4 C13 -0.2(3) . . . . ?
C3 C4 C13 C12 179.45(19) . . . . ?
C3 C4 C13 C14 0.2(3) . . . . ?
C4 N1 C5 C6 -177.45(17) . . . . ?
C4 N1 C5 C11 0.2(3) . . . . ?
C4 C13 C14 C1 -0.3(3) . . . . ?
C5 N1 C4 C3 -179.68(19) . . . . ?
C5 N1 C4 C13 0.1(3) . . . . ?
C5 C6 C7 C8 86.2(2) . . . . ?
C5 C6 C7 C17 -93.2(2) . . . . ?
C5 C11 C12 C13 0.1(3) . . . . ?
C6 C5 C11 C12 177.22(19) . . . . ?
C6 C7 C8 C9 179.90(19) . . . . ?
C6 C7 C17 C16 -179.7(2) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C7 C17 C16 0.9(3) . . . . ?
C8 C9 C10 C16 1.0(4) . . . . ?
C9 C10 C16 C17 -0.8(4) . . . . ?
C10 C16 C17 C7 -0.1(4) . . . . ?
C11 C5 C6 O1 167.00(19) . . . . ?
C11 C5 C6 C7 48.2(3) . . . . ?
C11 C5 C6 C15 -75.2(2) . . . . ?
C11 C12 C13 C4 0.2(3) . . . . ?
C11 C12 C13 C14 179.4(2) . . . . ?
C12 C13 C14 C1 -179.4(2) . . . . ?
C14 C1 C2 C3 -0.2(3) . . . . ?
C15 C6 C7 C8 -152.72(19) . . . . ?
C15 C6 C7 C17 27.9(3) . . . . ?
C17 C7 C8 C9 -0.7(3) . . . . ?

_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_4_xlp_20250329_01m
_database_code_depnum_ccdc_archive 'CCDC 2477839'
loop_
_audit_author_name
_audit_author_address
haokunzhuang
;shenzhen university of advanced technology
China
;
_audit_update_record             
;
2025-08-01 deposited with the CCDC.	2026-01-18 downloaded from the CCDC.
;
_audit_creation_date             2025-06-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H15 N O)'
_chemical_formula_sum            'C34 H30 N2 O2'
_chemical_formula_weight         498.60
_chemical_absolute_configuration rm
_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 0.0181 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'

_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                   5.7693(2)
_cell_length_b                   7.6573(2)
_cell_length_c                   14.5001(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.440(2)
_cell_angle_gamma                90
_cell_volume                     639.42(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7656
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      68.41
_cell_measurement_theta_min      3.05
_shelx_estimated_absorpt_T_max   0.884
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6026
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0819 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.8002.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1539
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11407
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.436
_diffrn_reflns_theta_min         3.053
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON II area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_oxdiff_ac3_digest_hkl    419d8a96cc49d0121feb360fa532bf96220b82
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2274
_reflns_number_total             2334
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 994 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.045
_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)+(0.0482P)²+0.2360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1192
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C006(H006), C007(H007), C009(H009), C00B(H00B), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I)
1.b Idealised Me refined as rotating group:
 C00J(H00A,H00C,H00J)
1.c Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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
O001 O 0.6276(3) 0.3191(3) 0.77843(14) 0.0213(5) Uani 1 1 d . . . . .
H001 H 0.659315 0.292371 0.724429 0.032 Uiso 1 1 calc R U . . .
N002 N 0.4285(4) 0.3575(3) 0.61510(17) 0.0166(5) Uani 1 1 d . . . . .
C003 C 0.5343(5) 0.6431(4) 0.8519(2) 0.0204(6) Uani 1 1 d . . . . .
H003 H 0.667194 0.632352 0.816682 0.025 Uiso 1 1 calc R U . . .
C004 C 0.3536(5) 0.3864(4) 0.5253(2) 0.0155(6) Uani 1 1 d . . . . .
C005 C 0.1350(5) 0.4651(4) 0.5012(2) 0.0171(6) Uani 1 1 d . . . . .
C006 C -0.0036(5) 0.5143(4) 0.5741(2) 0.0182(6) Uani 1 1 d . . . . .
H006 H -0.150326 0.567940 0.560924 0.022 Uiso 1 1 calc R U . . .
C007 C 0.4983(5) 0.3371(4) 0.4548(2) 0.0187(6) Uani 1 1 d . . . . .
H007 H 0.644527 0.284509 0.470441 0.022 Uiso 1 1 calc R U . . .
C008 C 0.3874(5) 0.3600(4) 0.7798(2) 0.0178(6) Uani 1 1 d . . . . .
C009 C 0.0739(5) 0.4846(4) 0.66348(19) 0.0180(6) Uani 1 1 d . . . . .
H009 H -0.017840 0.516938 0.712987 0.022 Uiso 1 1 calc R U . . .
C00A C 0.2938(5) 0.4045(4) 0.68122(19) 0.0158(6) Uani 1 1 d . . . . .
C00B C 0.4294(5) 0.3648(4) 0.3634(2) 0.0207(6) Uani 1 1 d . . . . .
H00B H 0.528440 0.331014 0.316481 0.025 Uiso 1 1 calc R U . . .
C00C C 0.3610(5) 0.5155(4) 0.84437(18) 0.0167(6) Uani 1 1 d . . . . .
C00D C 0.0689(5) 0.4927(4) 0.4061(2) 0.0193(6) Uani 1 1 d . . . . .
H00D H -0.076078 0.546075 0.389232 0.023 Uiso 1 1 calc R U . . .
C00E C 0.1663(5) 0.5359(4) 0.8962(2) 0.0214(7) Uani 1 1 d . . . . .
H00E H 0.045373 0.451521 0.891415 0.026 Uiso 1 1 calc R U . . .
C00F C 0.1479(5) 0.6783(5) 0.9545(2) 0.0256(7) Uani 1 1 d . . . . .
H00F H 0.014612 0.690513 0.989338 0.031 Uiso 1 1 calc R U . . .
C00G C 0.3220(6) 0.8029(4) 0.9623(2) 0.0260(7) Uani 1 1 d . . . . .
H00G H 0.309807 0.899308 1.002940 0.031 Uiso 1 1 calc R U . . .
C00H C 0.2121(5) 0.4432(4) 0.3388(2) 0.0212(6) Uani 1 1 d . . . . .
H00H H 0.165560 0.461373 0.275538 0.025 Uiso 1 1 calc R U . . .
C00I C 0.5145(6) 0.7850(4) 0.9101(2) 0.0257(7) Uani 1 1 d . . . . .
H00I H 0.633562 0.870833 0.914269 0.031 Uiso 1 1 calc R U . . .
C00J C 0.2580(5) 0.1970(4) 0.8121(2) 0.0224(6) Uani 1 1 d . . . . .
H00A H 0.293837 0.097217 0.773112 0.034 Uiso 1 1 calc R U . . .
H00C H 0.090390 0.218929 0.807252 0.034 Uiso 1 1 calc R U . . .
H00J H 0.307647 0.171308 0.876494 0.034 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
O001 H001 0.8400 . ?
O001 C008 1.422(3) . ?
N002 C004 1.366(4) . ?
N002 C00A 1.320(4) . ?
C003 H003 0.9500 . ?
C003 C00C 1.397(4) . ?
C003 C00I 1.385(4) . ?
C004 C005 1.422(4) . ?
C004 C007 1.409(4) . ?
C005 C006 1.415(4) . ?
C005 C00D 1.424(4) . ?
C006 H006 0.9500 . ?
C006 C009 1.364(4) . ?
C007 H007 0.9500 . ?
C007 C00B 1.377(4) . ?
C008 C00A 1.536(4) . ?
C008 C00C 1.528(4) . ?
C008 C00J 1.541(4) . ?
C009 H009 0.9500 . ?
C009 C00A 1.418(4) . ?
C00B H00B 0.9500 . ?
C00B C00H 1.416(4) . ?
C00C C00E 1.397(4) . ?
C00D H00D 0.9500 . ?
C00D C00H 1.370(4) . ?
C00E H00E 0.9500 . ?
C00E C00F 1.388(4) . ?
C00F H00F 0.9500 . ?
C00F C00G 1.384(5) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.388(5) . ?
C00H H00H 0.9500 . ?
C00I H00I 0.9500 . ?
C00J H00A 0.9800 . ?
C00J H00C 0.9800 . ?
C00J H00J 0.9800 . ?

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
C008 O001 H001 109.5 . . ?
C00A N002 C004 118.8(2) . . ?
C00C C003 H003 119.6 . . ?
C00I C003 H003 119.6 . . ?
C00I C003 C00C 120.8(3) . . ?
N002 C004 C005 121.9(2) . . ?
N002 C004 C007 118.8(2) . . ?
C007 C004 C005 119.4(3) . . ?
C004 C005 C00D 118.8(3) . . ?
C006 C005 C004 117.5(3) . . ?
C006 C005 C00D 123.6(3) . . ?
C005 C006 H006 120.1 . . ?
C009 C006 C005 119.9(3) . . ?
C009 C006 H006 120.1 . . ?
C004 C007 H007 119.8 . . ?
C00B C007 C004 120.5(3) . . ?
C00B C007 H007 119.8 . . ?
O001 C008 C00A 108.9(2) . . ?
O001 C008 C00C 108.2(2) . . ?
O001 C008 C00J 108.4(2) . . ?
C00A C008 C00J 108.3(2) . . ?
C00C C008 C00A 110.8(2) . . ?
C00C C008 C00J 112.1(2) . . ?
C006 C009 H009 120.6 . . ?
C006 C009 C00A 118.9(2) . . ?
C00A C009 H009 120.6 . . ?
N002 C00A C008 115.2(2) . . ?
N002 C00A C009 123.1(2) . . ?
C009 C00A C008 121.7(2) . . ?
C007 C00B H00B 119.7 . . ?
C007 C00B C00H 120.5(3) . . ?
C00H C00B H00B 119.7 . . ?
C003 C00C C008 119.7(2) . . ?
C00E C00C C003 118.3(3) . . ?
C00E C00C C008 122.0(3) . . ?
C005 C00D H00D 119.6 . . ?
C00H C00D C005 120.8(3) . . ?
C00H C00D H00D 119.6 . . ?
C00C C00E H00E 119.7 . . ?
C00F C00E C00C 120.6(3) . . ?
C00F C00E H00E 119.7 . . ?
C00E C00F H00F 119.7 . . ?
C00G C00F C00E 120.7(3) . . ?
C00G C00F H00F 119.7 . . ?
C00F C00G H00G 120.4 . . ?
C00F C00G C00I 119.2(3) . . ?
C00I C00G H00G 120.4 . . ?
C00B C00H H00H 120.0 . . ?
C00D C00H C00B 120.0(3) . . ?
C00D C00H H00H 120.0 . . ?
C003 C00I C00G 120.5(3) . . ?
C003 C00I H00I 119.7 . . ?
C00G C00I H00I 119.7 . . ?
C008 C00J H00A 109.5 . . ?
C008 C00J H00C 109.5 . . ?
C008 C00J H00J 109.5 . . ?
H00A C00J H00C 109.5 . . ?
H00A C00J H00J 109.5 . . ?
H00C C00J H00J 109.5 . . ?

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
O001 C008 C00A N002 15.4(3) . . . . ?
O001 C008 C00A C009 -166.9(3) . . . . ?
O001 C008 C00C C003 32.8(3) . . . . ?
O001 C008 C00C C00E -147.8(3) . . . . ?
N002 C004 C005 C006 0.4(4) . . . . ?
N002 C004 C005 C00D 179.5(3) . . . . ?
N002 C004 C007 C00B -179.7(3) . . . . ?
C003 C00C C00E C00F -0.9(4) . . . . ?
C004 N002 C00A C008 177.5(2) . . . . ?
C004 N002 C00A C009 -0.2(4) . . . . ?
C004 C005 C006 C009 -0.4(4) . . . . ?
C004 C005 C00D C00H 0.5(4) . . . . ?
C004 C007 C00B C00H 0.0(4) . . . . ?
C005 C004 C007 C00B 0.0(4) . . . . ?
C005 C006 C009 C00A 0.1(4) . . . . ?
C005 C00D C00H C00B -0.5(5) . . . . ?
C006 C005 C00D C00H 179.5(3) . . . . ?
C006 C009 C00A N002 0.2(4) . . . . ?
C006 C009 C00A C008 -177.3(3) . . . . ?
C007 C004 C005 C006 -179.3(3) . . . . ?
C007 C004 C005 C00D -0.3(4) . . . . ?
C007 C00B C00H C00D 0.2(5) . . . . ?
C008 C00C C00E C00F 179.8(3) . . . . ?
C00A N002 C004 C005 -0.2(4) . . . . ?
C00A N002 C004 C007 179.6(3) . . . . ?
C00A C008 C00C C003 -86.6(3) . . . . ?
C00A C008 C00C C00E 92.8(3) . . . . ?
C00C C003 C00I C00G 0.2(4) . . . . ?
C00C C008 C00A N002 134.4(2) . . . . ?
C00C C008 C00A C009 -47.9(3) . . . . ?
C00C C00E C00F C00G 0.1(5) . . . . ?
C00D C005 C006 C009 -179.4(3) . . . . ?
C00E C00F C00G C00I 0.9(5) . . . . ?
C00F C00G C00I C003 -1.0(5) . . . . ?
C00I C003 C00C C008 -179.9(3) . . . . ?
C00I C003 C00C C00E 0.8(4) . . . . ?
C00J C008 C00A N002 -102.3(3) . . . . ?
C00J C008 C00A C009 75.4(3) . . . . ?
C00J C008 C00C C003 152.4(3) . . . . ?
C00J C008 C00C C00E -28.3(4) . . . . ?

_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_3_xlp_20250325_01m
_database_code_depnum_ccdc_archive 'CCDC 2477837'
loop_
_audit_author_name
_audit_author_address
haokunzhuang
;shenzhen university of advanced technology
China
;
_audit_update_record             
;
2025-08-01 deposited with the CCDC.	2026-01-18 downloaded from the CCDC.
;
_audit_creation_date             2025-06-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         '2(C18 H17 N O2)'
_chemical_formula_sum            'C36 H34 N2 O4'
_chemical_formula_weight         558.65
_chemical_absolute_configuration rm
_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 0.0181 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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   6.1697(2)
_cell_length_b                   12.7061(3)
_cell_length_c                   18.3662(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1439.78(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9769
_cell_measurement_temperature    179.00
_cell_measurement_theta_max      68.34
_cell_measurement_theta_min      4.23
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1007 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.9181.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1581
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            50573
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.412
_diffrn_reflns_theta_min         4.231
_diffrn_ambient_temperature      179.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_oxdiff_ac3_digest_hkl    01d01763e36aced68599e7dd9793529abc85d3
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2596
_reflns_number_total             2639
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1067 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.1824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0835
_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 Ternary CH refined with riding coordinates:
 C00D(H00e)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00a,H00b)
2.c Aromatic/amide H refined with riding coordinates:
 C005(H005), C00A(H00c), C00C(H00d), C00E(H00f), C00F(H00g), C00G(H00h),
 C00I(H00j), C00K(H00n), C00L(H00o)
2.d Idealised Me refined as rotating group:
 C00J(H00k,H00l,H00m)
;
_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
O001 O 0.9464(2) 0.20027(9) 0.72963(7) 0.0281(3) Uani 1 1 d . . . . .
O002 O 0.7237(3) 0.10243(10) 0.79810(8) 0.0456(4) Uani 1 1 d . . . . .
N003 N 0.7292(2) 0.28503(10) 0.80568(7) 0.0234(3) Uani 1 1 d . . . . .
C004 C 0.8344(3) 0.33055(12) 0.64081(8) 0.0196(3) Uani 1 1 d . . . . .
C005 C 0.7027(3) 0.25340(13) 0.61138(9) 0.0230(3) Uani 1 1 d . . . . .
H005 H 0.695702 0.186218 0.633959 0.028 Uiso 1 1 calc R U . . .
C006 C 0.7892(3) 0.18833(14) 0.78058(9) 0.0285(4) Uani 1 1 d . . . . .
C007 C 0.9680(3) 0.31116(13) 0.70945(9) 0.0221(4) Uani 1 1 d . . . . .
C008 C 0.7629(3) 0.47062(12) 0.77098(9) 0.0253(4) Uani 1 1 d . . . . .
H00A H 0.640635 0.464684 0.736299 0.030 Uiso 1 1 calc R U . . .
H00B H 0.864150 0.525068 0.752844 0.030 Uiso 1 1 calc R U . . .
C009 C 0.5394(3) 0.41460(14) 0.87819(9) 0.0272(4) Uani 1 1 d . . . . .
C00A C 0.8456(3) 0.42831(14) 0.60594(9) 0.0270(4) Uani 1 1 d . . . . .
H00C H 0.939204 0.481396 0.624336 0.032 Uiso 1 1 calc R U . . .
C00B C 0.5654(3) 0.30848(14) 0.85717(8) 0.0242(4) Uani 1 1 d . . . . .
C00C C 0.5868(3) 0.37045(16) 0.51642(9) 0.0311(4) Uani 1 1 d . . . . .
H00D H 0.500091 0.384483 0.474784 0.037 Uiso 1 1 calc R U . . .
C00D C 0.8782(3) 0.36597(13) 0.77801(9) 0.0218(4) Uani 1 1 d . . . . .
H00E H 0.999340 0.374278 0.813711 0.026 Uiso 1 1 calc R U . . .
C00E C 0.4271(3) 0.23135(15) 0.88478(10) 0.0337(4) Uani 1 1 d . . . . .
H00F H 0.442391 0.160243 0.869643 0.040 Uiso 1 1 calc R U . . .
C00F C 0.5803(3) 0.27277(16) 0.54926(9) 0.0301(4) Uani 1 1 d . . . . .
H00G H 0.492033 0.218672 0.529357 0.036 Uiso 1 1 calc R U . . .
C00G C 0.7210(3) 0.44805(14) 0.54475(9) 0.0322(4) Uani 1 1 d . . . . .
H00H H 0.727356 0.515127 0.521997 0.039 Uiso 1 1 calc R U . . .
C00H C 0.6794(4) 0.50027(14) 0.84640(10) 0.0347(4) Uani 1 1 d . . . . .
H00I H 0.804034 0.513330 0.879130 0.042 Uiso 1 1 calc R U . . .
H00J H 0.594301 0.566137 0.843004 0.042 Uiso 1 1 calc R U . . .
C00I C 0.3776(3) 0.43841(17) 0.92811(10) 0.0359(5) Uani 1 1 d . . . . .
H00K H 0.359006 0.509409 0.943083 0.043 Uiso 1 1 calc R U . . .
C00J C 1.2061(3) 0.33286(16) 0.69702(11) 0.0339(4) Uani 1 1 d . . . . .
H00L H 1.289572 0.308410 0.739160 0.051 Uiso 1 1 calc R U . . .
H00M H 1.228373 0.408666 0.690589 0.051 Uiso 1 1 calc R U . . .
H00N H 1.254827 0.295581 0.653268 0.051 Uiso 1 1 calc R U . . .
C00K C 0.2676(4) 0.25860(18) 0.93423(12) 0.0432(5) Uani 1 1 d . . . . .
H00O H 0.173917 0.205835 0.953042 0.052 Uiso 1 1 calc R U . . .
C00L C 0.2429(4) 0.36209(18) 0.95663(11) 0.0425(5) Uani 1 1 d . . . . .
H00P H 0.134665 0.380267 0.991202 0.051 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
O001 C006 1.356(2) . ?
O001 C007 1.463(2) . ?
O002 C006 1.208(2) . ?
N003 C006 1.364(2) . ?
N003 C00B 1.416(2) . ?
N003 C00D 1.470(2) . ?
C004 C005 1.383(2) . ?
C004 C007 1.526(2) . ?
C004 C00A 1.399(2) . ?
C005 H005 0.9500 . ?
C005 C00F 1.390(3) . ?
C007 C00D 1.542(2) . ?
C007 C00J 1.512(3) . ?
C008 H00A 0.9900 . ?
C008 H00B 0.9900 . ?
C008 C00D 1.514(2) . ?
C008 C00H 1.525(2) . ?
C009 C00B 1.412(2) . ?
C009 C00H 1.507(3) . ?
C009 C00I 1.389(3) . ?
C00A H00C 0.9500 . ?
C00A C00G 1.385(2) . ?
C00B C00E 1.395(3) . ?
C00C H00D 0.9500 . ?
C00C C00F 1.381(3) . ?
C00C C00G 1.389(3) . ?
C00D H00E 1.0000 . ?
C00E H00F 0.9500 . ?
C00E C00K 1.383(3) . ?
C00F H00G 0.9500 . ?
C00G H00H 0.9500 . ?
C00H H00I 0.9900 . ?
C00H H00J 0.9900 . ?
C00I H00K 0.9500 . ?
C00I C00L 1.380(3) . ?
C00J H00L 0.9800 . ?
C00J H00M 0.9800 . ?
C00J H00N 0.9800 . ?
C00K H00O 0.9500 . ?
C00K C00L 1.386(3) . ?
C00L H00P 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
C006 O001 C007 110.34(12) . . ?
C006 N003 C00B 127.53(15) . . ?
C006 N003 C00D 110.11(14) . . ?
C00B N003 C00D 122.01(14) . . ?
C005 C004 C007 121.70(14) . . ?
C005 C004 C00A 118.63(15) . . ?
C00A C004 C007 119.66(14) . . ?
C004 C005 H005 119.5 . . ?
C004 C005 C00F 120.96(16) . . ?
C00F C005 H005 119.5 . . ?
O001 C006 N003 109.07(14) . . ?
O002 C006 O001 121.63(16) . . ?
O002 C006 N003 129.30(18) . . ?
O001 C007 C004 108.41(13) . . ?
O001 C007 C00D 101.26(13) . . ?
O001 C007 C00J 107.59(14) . . ?
C004 C007 C00D 114.06(13) . . ?
C00J C007 C004 111.74(14) . . ?
C00J C007 C00D 112.95(14) . . ?
H00A C008 H00B 108.5 . . ?
C00D C008 H00A 110.2 . . ?
C00D C008 H00B 110.2 . . ?
C00D C008 C00H 107.35(14) . . ?
C00H C008 H00A 110.2 . . ?
C00H C008 H00B 110.2 . . ?
C00B C009 C00H 121.24(16) . . ?
C00I C009 C00B 118.05(17) . . ?
C00I C009 C00H 120.69(17) . . ?
C004 C00A H00C 119.8 . . ?
C00G C00A C004 120.33(16) . . ?
C00G C00A H00C 119.8 . . ?
C009 C00B N003 117.69(15) . . ?
C00E C00B N003 122.12(16) . . ?
C00E C00B C009 120.15(17) . . ?
C00F C00C H00D 120.3 . . ?
C00F C00C C00G 119.46(16) . . ?
C00G C00C H00D 120.3 . . ?
N003 C00D C007 101.02(13) . . ?
N003 C00D C008 110.51(14) . . ?
N003 C00D H00E 108.3 . . ?
C007 C00D H00E 108.3 . . ?
C008 C00D C007 119.73(14) . . ?
C008 C00D H00E 108.3 . . ?
C00B C00E H00F 120.1 . . ?
C00K C00E C00B 119.87(19) . . ?
C00K C00E H00F 120.1 . . ?
C005 C00F H00G 119.9 . . ?
C00C C00F C005 120.13(17) . . ?
C00C C00F H00G 119.9 . . ?
C00A C00G C00C 120.44(16) . . ?
C00A C00G H00H 119.8 . . ?
C00C C00G H00H 119.8 . . ?
C008 C00H H00I 109.3 . . ?
C008 C00H H00J 109.3 . . ?
C009 C00H C008 111.53(14) . . ?
C009 C00H H00I 109.3 . . ?
C009 C00H H00J 109.3 . . ?
H00I C00H H00J 108.0 . . ?
C009 C00I H00K 119.0 . . ?
C00L C00I C009 122.02(19) . . ?
C00L C00I H00K 119.0 . . ?
C007 C00J H00L 109.5 . . ?
C007 C00J H00M 109.5 . . ?
C007 C00J H00N 109.5 . . ?
H00L C00J H00M 109.5 . . ?
H00L C00J H00N 109.5 . . ?
H00M C00J H00N 109.5 . . ?
C00E C00K H00O 119.7 . . ?
C00E C00K C00L 120.7(2) . . ?
C00L C00K H00O 119.7 . . ?
C00I C00L C00K 119.20(19) . . ?
C00I C00L H00P 120.4 . . ?
C00K C00L H00P 120.4 . . ?

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
O001 C007 C00D N003 -27.27(15) . . . . ?
O001 C007 C00D C008 -148.75(14) . . . . ?
N003 C00B C00E C00K -179.09(17) . . . . ?
C004 C005 C00F C00C -0.8(3) . . . . ?
C004 C007 C00D N003 88.93(16) . . . . ?
C004 C007 C00D C008 -32.6(2) . . . . ?
C004 C00A C00G C00C -1.3(3) . . . . ?
C005 C004 C007 O001 6.0(2) . . . . ?
C005 C004 C007 C00D -105.96(17) . . . . ?
C005 C004 C007 C00J 124.41(17) . . . . ?
C005 C004 C00A C00G 2.3(2) . . . . ?
C006 O001 C007 C004 -95.96(15) . . . . ?
C006 O001 C007 C00D 24.34(17) . . . . ?
C006 O001 C007 C00J 143.04(14) . . . . ?
C006 N003 C00B C009 176.51(17) . . . . ?
C006 N003 C00B C00E -5.9(3) . . . . ?
C006 N003 C00D C007 23.34(17) . . . . ?
C006 N003 C00D C008 151.10(14) . . . . ?
C007 O001 C006 O002 169.95(17) . . . . ?
C007 O001 C006 N003 -10.62(19) . . . . ?
C007 C004 C005 C00F 179.30(15) . . . . ?
C007 C004 C00A C00G -178.25(16) . . . . ?
C009 C00B C00E C00K -1.6(3) . . . . ?
C009 C00I C00L C00K -0.8(3) . . . . ?
C00A C004 C005 C00F -1.2(2) . . . . ?
C00A C004 C007 O001 -173.47(14) . . . . ?
C00A C004 C007 C00D 74.57(19) . . . . ?
C00A C004 C007 C00J -55.1(2) . . . . ?
C00B N003 C006 O001 177.57(14) . . . . ?
C00B N003 C006 O002 -3.1(3) . . . . ?
C00B N003 C00D C007 -162.93(13) . . . . ?
C00B N003 C00D C008 -35.2(2) . . . . ?
C00B C009 C00H C008 26.3(3) . . . . ?
C00B C009 C00I C00L -0.5(3) . . . . ?
C00B C00E C00K C00L 0.2(3) . . . . ?
C00D N003 C006 O001 -9.1(2) . . . . ?
C00D N003 C006 O002 170.2(2) . . . . ?
C00D N003 C00B C009 3.9(2) . . . . ?
C00D N003 C00B C00E -178.49(16) . . . . ?
C00D C008 C00H C009 -55.1(2) . . . . ?
C00E C00K C00L C00I 1.0(3) . . . . ?
C00F C00C C00G C00A -0.8(3) . . . . ?
C00G C00C C00F C005 1.8(3) . . . . ?
C00H C008 C00D N003 59.27(18) . . . . ?
C00H C008 C00D C007 175.92(15) . . . . ?
C00H C009 C00B N003 0.7(2) . . . . ?
C00H C009 C00B C00E -176.96(17) . . . . ?
C00H C009 C00I C00L 178.18(19) . . . . ?
C00I C009 C00B N003 179.36(15) . . . . ?
C00I C009 C00B C00E 1.7(3) . . . . ?
C00I C009 C00H C008 -152.38(17) . . . . ?
C00J C007 C00D N003 -142.04(15) . . . . ?
C00J C007 C00D C008 96.48(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
