# 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_lan_auto
_database_code_depnum_ccdc_archive 'CCDC 2529736'
loop_
_audit_author_name
_audit_author_address
sss
;Chinese Academy of Sciences Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2026-02-09 deposited with the CCDC.	2026-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N O4'
_chemical_formula_sum            'C25 H25 N O4'
_chemical_formula_weight         403.46

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.3579(2)
_cell_length_b                   11.4992(2)
_cell_length_c                   10.7787(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.485(2)
_cell_angle_gamma                90
_cell_volume                     1034.02(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19274
_cell_measurement_theta_min      3.8720
_cell_measurement_theta_max      76.1750

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.707
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.127a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            22915
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.1592
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.109
_diffrn_reflns_theta_max         76.517
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4188
_reflns_number_gt                4130
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.930
_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       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_computing_publication_material  'CrysAlisPro 1.171.43.127a (Rigaku OD, 2024)'
_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)+(0.1282P)²+0.4590P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1756 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4188
_refine_ls_number_parameters     275
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1850
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O28 O 0.9224(3) 0.4822(2) 0.8017(3) 0.0250(6) Uani 1 1 d . . . . .
O25 O 0.9901(3) 0.7435(3) 0.8430(2) 0.0264(6) Uani 1 1 d . . . . .
O27 O 1.1771(3) 0.7223(3) 0.7042(3) 0.0307(7) Uani 1 1 d . . . . .
O22 O 0.2486(3) 0.2350(3) 0.9125(3) 0.0279(6) Uani 1 1 d . . . . .
N11 N 0.6788(3) 0.5483(3) 0.7155(3) 0.0177(6) Uani 1 1 d . . . . .
C20 C 0.3048(4) 0.4110(4) 0.8148(3) 0.0230(8) Uani 1 1 d . . . . .
H20 H 0.193717 0.428734 0.814394 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3615(4) 0.3059(3) 0.8646(3) 0.0204(7) Uani 1 1 d . . . . .
C12 C 0.8410(4) 0.5491(3) 0.7346(3) 0.0186(7) Uani 1 1 d . . . . .
C17 C 0.6287(4) 0.3593(3) 0.8141(3) 0.0212(7) Uani 1 1 d . . . . .
H17 H 0.739512 0.341139 0.813835 0.025 Uiso 1 1 calc R U . . .
C24 C 1.0423(4) 0.7078(3) 0.7356(3) 0.0211(7) Uani 1 1 d . . . . .
C18 C 0.5238(5) 0.2800(3) 0.8628(3) 0.0232(8) Uani 1 1 d . . . . .
H18 H 0.563173 0.207888 0.895045 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5732(4) 0.4652(3) 0.7656(3) 0.0172(7) Uani 1 1 d . . . . .
C14 C 0.7636(4) 0.7219(3) 0.6199(3) 0.0206(7) Uani 1 1 d . . . . .
H14 H 0.756207 0.783534 0.684772 0.025 Uiso 1 1 calc R U . . .
C21 C 0.4094(4) 0.4898(3) 0.7659(3) 0.0215(7) Uani 1 1 d . . . . .
H21 H 0.369512 0.561267 0.732274 0.026 Uiso 1 1 calc R U . . .
C1 C 0.5452(4) 0.5884(3) 0.5091(3) 0.0224(7) Uani 1 1 d . . . . .
C2 C 0.6289(5) 0.5026(4) 0.4442(4) 0.0270(8) Uani 1 1 d . . . . .
H2 H 0.729303 0.474833 0.478115 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4161(5) 0.5001(4) 0.2805(4) 0.0286(9) Uani 1 1 d . . . . .
C15 C 0.6173(4) 0.6398(3) 0.6302(3) 0.0191(7) Uani 1 1 d . . . . .
H15 H 0.531406 0.683443 0.671201 0.023 Uiso 1 1 calc R U . . .
C13 C 0.9097(4) 0.6461(3) 0.6579(3) 0.0188(7) Uani 1 1 d . . . . .
H13 H 0.954737 0.612446 0.581895 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5662(5) 0.4589(4) 0.3324(4) 0.0276(8) Uani 1 1 d . . . . .
H3 H 0.623276 0.401251 0.289955 0.033 Uiso 1 1 calc R U . . .
C9 C 0.3306(5) 0.5831(4) 0.3462(4) 0.0255(8) Uani 1 1 d . . . . .
C29 C 0.7730(5) 0.7836(4) 0.4946(3) 0.0268(8) Uani 1 1 d . . . . .
H29A H 0.781909 0.724497 0.428661 0.032 Uiso 1 1 calc R U . . .
H29B H 0.672412 0.827481 0.476143 0.032 Uiso 1 1 calc R U . . .
C10 C 0.4000(5) 0.6276(3) 0.4619(3) 0.0232(7) Uani 1 1 d . . . . .
H10 H 0.344195 0.684830 0.505857 0.028 Uiso 1 1 calc R U . . .
C23 C 0.3065(5) 0.1324(4) 0.9745(4) 0.0294(8) Uani 1 1 d . . . . .
H23A H 0.357925 0.082090 0.915317 0.044 Uiso 1 1 calc R U . . .
H23B H 0.216735 0.090923 1.008729 0.044 Uiso 1 1 calc R U . . .
H23C H 0.384686 0.153778 1.042140 0.044 Uiso 1 1 calc R U . . .
C30 C 0.9141(5) 0.8668(4) 0.4919(4) 0.0292(8) Uani 1 1 d . . . . .
H30A H 0.911356 0.906386 0.411219 0.044 Uiso 1 1 calc R U . . .
H30B H 1.014460 0.823156 0.504350 0.044 Uiso 1 1 calc R U . . .
H30C H 0.907402 0.924587 0.558198 0.044 Uiso 1 1 calc R U . . .
C8 C 0.1792(5) 0.6235(4) 0.2976(4) 0.0311(9) Uani 1 1 d . . . . .
H8 H 0.120819 0.678528 0.342671 0.037 Uiso 1 1 calc R U . . .
C26 C 1.1069(5) 0.8001(4) 0.9269(4) 0.0352(10) Uani 1 1 d . . . . .
H26A H 1.143705 0.871831 0.888734 0.053 Uiso 1 1 calc R U . . .
H26B H 1.198310 0.747986 0.944234 0.053 Uiso 1 1 calc R U . . .
H26C H 1.057822 0.818803 1.004790 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1174(6) 0.5826(4) 0.1848(4) 0.0362(10) Uani 1 1 d . . . . .
H7 H 0.015658 0.609167 0.152318 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3484(6) 0.4602(4) 0.1635(4) 0.0342(10) Uani 1 1 d . . . . .
H5 H 0.404213 0.404432 0.117414 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2027(6) 0.5021(5) 0.1172(4) 0.0394(11) Uani 1 1 d . . . . .
H6 H 0.159508 0.476112 0.038457 0.047 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
O28 C12 1.232(4) . ?
O25 C24 1.327(5) . ?
O25 C26 1.445(4) . ?
O27 C24 1.208(5) . ?
O22 C19 1.372(4) . ?
O22 C23 1.426(5) . ?
N11 C12 1.359(4) . ?
N11 C16 1.428(4) . ?
N11 C15 1.470(4) . ?
C20 C21 1.386(5) . ?
C20 C19 1.394(5) . ?
C20 H20 0.9500 . ?
C19 C18 1.390(5) . ?
C12 C13 1.522(5) . ?
C17 C18 1.390(5) . ?
C17 C16 1.393(5) . ?
C17 H17 0.9500 . ?
C24 C13 1.523(5) . ?
C18 H18 0.9500 . ?
C16 C21 1.398(5) . ?
C14 C29 1.531(5) . ?
C14 C13 1.536(5) . ?
C14 C15 1.555(5) . ?
C14 H14 1.0000 . ?
C21 H21 0.9500 . ?
C1 C10 1.364(5) . ?
C1 C2 1.419(6) . ?
C1 C15 1.524(5) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9500 . ?
C4 C9 1.408(6) . ?
C4 C3 1.423(6) . ?
C4 C5 1.427(6) . ?
C15 H15 1.0000 . ?
C13 H13 1.0000 . ?
C3 H3 0.9500 . ?
C9 C8 1.419(6) . ?
C9 C10 1.437(6) . ?
C29 C30 1.521(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C10 H10 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C8 C7 1.375(6) . ?
C8 H8 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C7 C6 1.400(7) . ?
C7 H7 0.9500 . ?
C5 C6 1.375(7) . ?
C5 H5 0.9500 . ?
C6 H6 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
C24 O25 C26 116.1(3) . . ?
C19 O22 C23 116.5(3) . . ?
C12 N11 C16 125.5(3) . . ?
C12 N11 C15 113.4(3) . . ?
C16 N11 C15 121.0(3) . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
O22 C19 C18 124.9(3) . . ?
O22 C19 C20 115.8(3) . . ?
C18 C19 C20 119.3(3) . . ?
O28 C12 N11 126.5(3) . . ?
O28 C12 C13 124.3(3) . . ?
N11 C12 C13 109.2(3) . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
O27 C24 O25 124.3(3) . . ?
O27 C24 C13 124.8(3) . . ?
O25 C24 C13 110.9(3) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C17 C16 C21 118.7(3) . . ?
C17 C16 N11 121.8(3) . . ?
C21 C16 N11 119.5(3) . . ?
C29 C14 C13 114.6(3) . . ?
C29 C14 C15 115.3(3) . . ?
C13 C14 C15 104.6(3) . . ?
C29 C14 H14 107.3 . . ?
C13 C14 H14 107.3 . . ?
C15 C14 H14 107.3 . . ?
C20 C21 C16 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C16 C21 H21 119.7 . . ?
C10 C1 C2 120.0(4) . . ?
C10 C1 C15 119.2(3) . . ?
C2 C1 C15 120.8(3) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C9 C4 C3 119.4(4) . . ?
C9 C4 C5 118.5(4) . . ?
C3 C4 C5 122.2(4) . . ?
N11 C15 C1 111.3(3) . . ?
N11 C15 C14 103.5(3) . . ?
C1 C15 C14 116.5(3) . . ?
N11 C15 H15 108.4 . . ?
C1 C15 H15 108.4 . . ?
C14 C15 H15 108.4 . . ?
C12 C13 C24 109.2(3) . . ?
C12 C13 C14 103.9(3) . . ?
C24 C13 C14 115.0(3) . . ?
C12 C13 H13 109.5 . . ?
C24 C13 H13 109.5 . . ?
C14 C13 H13 109.5 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C9 C8 120.3(4) . . ?
C4 C9 C10 119.1(4) . . ?
C8 C9 C10 120.5(4) . . ?
C30 C29 C14 113.0(3) . . ?
C30 C29 H29A 109.0 . . ?
C14 C29 H29A 109.0 . . ?
C30 C29 H29B 109.0 . . ?
C14 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C1 C10 C9 120.6(4) . . ?
C1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C6 C5 C4 120.2(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.7(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.100



####################################################################### 
# 
# 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_lan-3_auto
_database_code_depnum_ccdc_archive 'CCDC 2529735'
loop_
_audit_author_name
_audit_author_address
ggg
;Chinese Academy of Sciences Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2026-02-09 deposited with the CCDC.	2026-05-20 downloaded from the CCDC.
;
_audit_creation_date             2025-11-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H18 O2'
_chemical_formula_sum            'C13 H18 O2'
_chemical_formula_weight         206.27
_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 0.0181 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'
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                   9.6463(3)
_cell_length_b                   5.90560(10)
_cell_length_c                   10.8390(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.744(3)
_cell_angle_gamma                90
_cell_volume                     594.30(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4772
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.4340
_cell_measurement_theta_min      4.2330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.44.128a (Rigaku Oxford Diffraction, 2025)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_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  0.0160
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5222
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.585
_diffrn_reflns_theta_min         4.238
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'ROD, SynergyCustom system, HyPix'
_diffrn_measurement_method       'four-circle diffractometer'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                2185
_reflns_number_total             2197
_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       
'CrysAlisPro system (CCD 44.128a 64-bit (release 04-11-2025))'
_computing_data_collection       
'CrysAlisPro system (CCD 44.128a 64-bit (release 04-11-2025))'
_computing_data_reduction        
'CrysAlisPro system (CCD 44.128a 64-bit (release 04-11-2025))'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 884 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0285
_refine_ls_restrained_S_all      1.087
_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)+(0.0474P)²+0.0872P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C006(H006), C008(H008)
1.b Secondary CH2 refined with riding coordinates:
 C004(H00A,H00B), C005(H00C,H00D), C009(H00E,H00F)
1.c Aromatic/amide H refined with riding coordinates:
 C00A(H00G), C00B(H00H), C00C(H00I), C00E(H00M), C00F(H00N)
1.d Idealised Me refined as rotating group:
 C00D(H00J,H00K,H00L)
1.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.04558(11) 0.76163(19) 0.08640(9) 0.0186(2) Uani 1 1 d . . . . .
H001 H 0.050878 0.885048 0.125939 0.028 Uiso 1 1 calc R U . . .
O002 O 0.08416(12) 0.18989(19) 0.16508(10) 0.0246(3) Uani 1 1 d . . . . .
H002 H 0.047384 0.240867 0.091063 0.037 Uiso 1 1 calc R U . . .
C003 C 0.21056(15) 0.5350(3) 0.24879(12) 0.0145(3) Uani 1 1 d . . . . .
C004 C 0.18344(15) 0.6526(3) 0.12087(13) 0.0162(3) Uani 1 1 d . . . . .
H00A H 0.259722 0.766667 0.124869 0.019 Uiso 1 1 calc R U . . .
H00B H 0.187885 0.540317 0.054202 0.019 Uiso 1 1 calc R U . . .
C005 C 0.09540(15) 0.3679(3) 0.25684(13) 0.0172(3) Uani 1 1 d . . . . .
H00C H 0.118541 0.302441 0.344152 0.021 Uiso 1 1 calc R U . . .
H00D H 0.001762 0.447122 0.240925 0.021 Uiso 1 1 calc R U . . .
C006 C 0.36638(15) 0.4767(3) 0.31708(13) 0.0165(3) Uani 1 1 d . . . . .
H006 H 0.377044 0.336481 0.370575 0.020 Uiso 1 1 calc R U . . .
C007 C 0.48335(15) 0.5072(3) 0.25193(13) 0.0193(3) Uani 1 1 d . . . . .
C008 C 0.29184(15) 0.6684(3) 0.36582(12) 0.0166(3) Uani 1 1 d . . . . .
H008 H 0.322813 0.822288 0.345444 0.020 Uiso 1 1 calc R U . . .
C009 C 0.25726(17) 0.6546(3) 0.49377(13) 0.0215(3) Uani 1 1 d . . . . .
H00E H 0.344252 0.694579 0.562889 0.026 Uiso 1 1 calc R U . . .
H00F H 0.230655 0.496880 0.508362 0.026 Uiso 1 1 calc R U . . .
C00A C 0.50346(18) 0.3388(3) 0.16841(15) 0.0249(4) Uani 1 1 d . . . . .
H00G H 0.443095 0.208946 0.154480 0.030 Uiso 1 1 calc R U . . .
C00B C 0.57306(17) 0.6949(3) 0.27113(16) 0.0265(4) Uani 1 1 d . . . . .
H00H H 0.561296 0.811208 0.327983 0.032 Uiso 1 1 calc R U . . .
C00C C 0.69911(18) 0.5469(4) 0.12514(16) 0.0319(4) Uani 1 1 d . . . . .
H00I H 0.772337 0.560630 0.082063 0.038 Uiso 1 1 calc R U . . .
C00D C 0.1347(2) 0.8118(3) 0.50057(17) 0.0329(4) Uani 1 1 d . . . . .
H00J H 0.047450 0.769520 0.434171 0.049 Uiso 1 1 calc R U . . .
H00K H 0.160848 0.968275 0.486802 0.049 Uiso 1 1 calc R U . . .
H00L H 0.116961 0.798823 0.585118 0.049 Uiso 1 1 calc R U . . .
C00E C 0.68075(18) 0.7143(4) 0.20749(18) 0.0333(4) Uani 1 1 d . . . . .
H00M H 0.741478 0.843782 0.221214 0.040 Uiso 1 1 calc R U . . .
C00F C 0.61048(19) 0.3579(4) 0.10515(16) 0.0307(4) Uani 1 1 d . . . . .
H00N H 0.622848 0.241831 0.048385 0.037 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 C004 1.4330(17) . ?
O002 H002 0.8400 . ?
O002 C005 1.4309(19) . ?
C003 C004 1.5088(18) . ?
C003 C005 1.506(2) . ?
C003 C006 1.5237(19) . ?
C003 C008 1.5182(19) . ?
C004 H00A 0.9900 . ?
C004 H00B 0.9900 . ?
C005 H00C 0.9900 . ?
C005 H00D 0.9900 . ?
C006 H006 1.0000 . ?
C006 C007 1.496(2) . ?
C006 C008 1.511(2) . ?
C007 C00A 1.393(2) . ?
C007 C00B 1.387(2) . ?
C008 H008 1.0000 . ?
C008 C009 1.5140(19) . ?
C009 H00E 0.9900 . ?
C009 H00F 0.9900 . ?
C009 C00D 1.520(2) . ?
C00A H00G 0.9500 . ?
C00A C00F 1.390(2) . ?
C00B H00H 0.9500 . ?
C00B C00E 1.399(2) . ?
C00C H00I 0.9500 . ?
C00C C00E 1.375(3) . ?
C00C C00F 1.387(3) . ?
C00D H00J 0.9800 . ?
C00D H00K 0.9800 . ?
C00D H00L 0.9800 . ?
C00E H00M 0.9500 . ?
C00F H00N 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
C004 O001 H001 109.5 . . ?
C005 O002 H002 109.5 . . ?
C004 C003 C006 116.91(12) . . ?
C004 C003 C008 116.77(13) . . ?
C005 C003 C004 114.09(11) . . ?
C005 C003 C006 118.02(12) . . ?
C005 C003 C008 120.89(11) . . ?
C008 C003 C006 59.58(9) . . ?
O001 C004 C003 111.33(11) . . ?
O001 C004 H00A 109.4 . . ?
O001 C004 H00B 109.4 . . ?
C003 C004 H00A 109.4 . . ?
C003 C004 H00B 109.4 . . ?
H00A C004 H00B 108.0 . . ?
O002 C005 C003 111.04(11) . . ?
O002 C005 H00C 109.4 . . ?
O002 C005 H00D 109.4 . . ?
C003 C005 H00C 109.4 . . ?
C003 C005 H00D 109.4 . . ?
H00C C005 H00D 108.0 . . ?
C003 C006 H006 113.7 . . ?
C007 C006 C003 120.97(12) . . ?
C007 C006 H006 113.7 . . ?
C007 C006 C008 124.49(14) . . ?
C008 C006 C003 60.03(9) . . ?
C008 C006 H006 113.7 . . ?
C00A C007 C006 118.47(15) . . ?
C00B C007 C006 123.06(14) . . ?
C00B C007 C00A 118.47(14) . . ?
C003 C008 H008 113.9 . . ?
C006 C008 C003 60.39(9) . . ?
C006 C008 H008 113.9 . . ?
C006 C008 C009 121.59(14) . . ?
C009 C008 C003 123.04(13) . . ?
C009 C008 H008 113.9 . . ?
C008 C009 H00E 109.2 . . ?
C008 C009 H00F 109.2 . . ?
C008 C009 C00D 112.26(13) . . ?
H00E C009 H00F 107.9 . . ?
C00D C009 H00E 109.2 . . ?
C00D C009 H00F 109.2 . . ?
C007 C00A H00G 119.5 . . ?
C00F C00A C007 121.04(17) . . ?
C00F C00A H00G 119.5 . . ?
C007 C00B H00H 119.7 . . ?
C007 C00B C00E 120.55(17) . . ?
C00E C00B H00H 119.7 . . ?
C00E C00C H00I 120.1 . . ?
C00E C00C C00F 119.84(15) . . ?
C00F C00C H00I 120.1 . . ?
C009 C00D H00J 109.5 . . ?
C009 C00D H00K 109.5 . . ?
C009 C00D H00L 109.5 . . ?
H00J C00D H00K 109.5 . . ?
H00J C00D H00L 109.5 . . ?
H00K C00D H00L 109.5 . . ?
C00B C00E H00M 119.8 . . ?
C00C C00E C00B 120.30(18) . . ?
C00C C00E H00M 119.8 . . ?
C00A C00F H00N 120.1 . . ?
C00C C00F C00A 119.80(17) . . ?
C00C C00F H00N 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
