# Supplementary Information (SI) for Journal of Materials Chemistry C.
# 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_mo_ddz20098_0m
_database_code_depnum_ccdc_archive 'CCDC 2159876'
loop_
_audit_author_name
_audit_author_address
obpo
;Wenzhou university
China
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2025-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 O2'
_chemical_formula_weight         212.24

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.328(2)
_cell_length_b                   9.678(2)
_cell_length_c                   13.941(3)
_cell_angle_alpha                88.153(6)
_cell_angle_beta                 71.728(6)
_cell_angle_gamma                69.913(7)
_cell_volume                     1118.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9113
_cell_measurement_theta_min      4.912
_cell_measurement_theta_max      54.894

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5640
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21472
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4372
_reflns_number_gt                3476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.1521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.067(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4372
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.03422(15) 0.03522(14) 0.21862(9) 0.0922(5) Uani 1 1 d . . . . .
O2 O 0.65127(11) 0.34119(12) 0.66381(7) 0.0603(3) Uani 1 1 d . . . . .
C1 C 0.73694(17) 0.35315(15) 0.18018(11) 0.0528(4) Uani 1 1 d . . . . .
H1 H 0.7304 0.4156 0.2319 0.063 Uiso 1 1 calc R U . . .
C2 C 0.66817(19) 0.41125(18) 0.10636(11) 0.0619(4) Uani 1 1 d . . . . .
H2 H 0.6177 0.5128 0.1077 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6744(2) 0.3191(2) 0.03098(12) 0.0711(5) Uani 1 1 d . . . . .
H3 H 0.6267 0.3583 -0.0179 0.085 Uiso 1 1 calc R U . . .
C4 C 0.7508(2) 0.1689(2) 0.02762(12) 0.0724(5) Uani 1 1 d . . . . .
H4 H 0.7543 0.1069 -0.0233 0.087 Uiso 1 1 calc R U . . .
C5 C 0.82248(19) 0.11038(18) 0.10001(12) 0.0624(4) Uani 1 1 d . . . . .
H5 H 0.8756 0.0090 0.0969 0.075 Uiso 1 1 calc R U . . .
C6 C 0.81563(16) 0.20197(15) 0.17725(10) 0.0500(3) Uani 1 1 d . . . . .
C7 C 0.90451(18) 0.13627(16) 0.24987(11) 0.0561(4) Uani 1 1 d . . . . .
C8 C 0.83685(15) 0.19296(14) 0.35825(10) 0.0465(3) Uani 1 1 d . . . . .
C9 C 0.93903(15) 0.16322(15) 0.41690(11) 0.0505(3) Uani 1 1 d . . . . .
H9 H 1.0483 0.1103 0.3865 0.061 Uiso 1 1 calc R U . . .
C10 C 0.88312(15) 0.20982(15) 0.51836(10) 0.0496(3) Uani 1 1 d . . . . .
H10 H 0.9541 0.1900 0.5555 0.060 Uiso 1 1 calc R U . . .
C11 C 0.71939(15) 0.28685(14) 0.56490(10) 0.0456(3) Uani 1 1 d . . . . .
C12 C 0.61466(15) 0.31385(15) 0.50828(10) 0.0495(3) Uani 1 1 d . . . . .
H12 H 0.5047 0.3627 0.5396 0.059 Uiso 1 1 calc R U . . .
C13 C 0.67211(15) 0.26911(15) 0.40705(10) 0.0487(3) Uani 1 1 d . . . . .
H13 H 0.6009 0.2895 0.3701 0.058 Uiso 1 1 calc R U . . .
C14 C 0.7532(2) 0.3130(2) 0.72549(12) 0.0751(5) Uani 1 1 d . . . . .
H14A H 0.8364 0.3538 0.6974 0.113 Uiso 1 1 calc R U . . .
H14B H 0.8013 0.2084 0.7276 0.113 Uiso 1 1 calc R U . . .
H14C H 0.6905 0.3579 0.7929 0.113 Uiso 1 1 calc R U . . .
O3 O 0.00126(13) 0.47608(13) 0.77927(9) 0.0773(4) Uani 1 1 d . . . . .
O4 O 0.34993(13) 0.14748(12) 0.33983(8) 0.0655(3) Uani 1 1 d . . . . .
C15 C 0.36744(16) 0.20690(15) 0.79431(10) 0.0521(3) Uani 1 1 d . . . . .
H15 H 0.4270 0.1878 0.7257 0.062 Uiso 1 1 calc R U . . .
C16 C 0.4422(2) 0.15274(17) 0.86641(12) 0.0622(4) Uani 1 1 d . . . . .
H16 H 0.5520 0.0980 0.8460 0.075 Uiso 1 1 calc R U . . .
C17 C 0.3545(2) 0.17977(19) 0.96803(13) 0.0712(5) Uani 1 1 d . . . . .
H17 H 0.4052 0.1432 1.0160 0.085 Uiso 1 1 calc R U . . .
C18 C 0.1919(2) 0.2609(2) 0.99883(12) 0.0730(5) Uani 1 1 d . . . . .
H18 H 0.1330 0.2785 1.0675 0.088 Uiso 1 1 calc R U . . .
C19 C 0.11640(19) 0.31597(17) 0.92808(11) 0.0617(4) Uani 1 1 d . . . . .
H19 H 0.0067 0.3710 0.9494 0.074 Uiso 1 1 calc R U . . .
C20 C 0.20311(16) 0.28994(15) 0.82469(10) 0.0487(3) Uani 1 1 d . . . . .
C21 C 0.12015(16) 0.36373(15) 0.75105(11) 0.0515(3) Uani 1 1 d . . . . .
C22 C 0.18420(14) 0.30503(14) 0.64263(10) 0.0447(3) Uani 1 1 d . . . . .
C23 C 0.25451(15) 0.15435(14) 0.61101(10) 0.0471(3) Uani 1 1 d . . . . .
H23 H 0.2672 0.0858 0.6588 0.057 Uiso 1 1 calc R U . . .
C24 C 0.30511(15) 0.10606(15) 0.51026(10) 0.0488(3) Uani 1 1 d . . . . .
H24 H 0.3487 0.0054 0.4907 0.059 Uiso 1 1 calc R U . . .
C25 C 0.29139(15) 0.20684(15) 0.43772(10) 0.0476(3) Uani 1 1 d . . . . .
C26 C 0.22105(16) 0.35689(15) 0.46747(11) 0.0512(3) Uani 1 1 d . . . . .
H26 H 0.2106 0.4251 0.4193 0.061 Uiso 1 1 calc R U . . .
C27 C 0.16679(15) 0.40403(15) 0.56895(11) 0.0496(3) Uani 1 1 d . . . . .
H27 H 0.1173 0.5046 0.5887 0.060 Uiso 1 1 calc R U . . .
C28 C 0.3367(2) 0.2459(2) 0.26190(13) 0.0850(6) Uani 1 1 d . . . . .
H28A H 0.3881 0.1905 0.1969 0.127 Uiso 1 1 calc R U . . .
H28B H 0.3883 0.3150 0.2660 0.127 Uiso 1 1 calc R U . . .
H28C H 0.2249 0.2985 0.2705 0.127 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 C7 1.2224(17) . ?
O2 C11 1.3600(16) . ?
O2 C14 1.4274(18) . ?
C1 C2 1.384(2) . ?
C1 C6 1.3887(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.496(2) . ?
C7 C8 1.483(2) . ?
C8 C9 1.3945(18) . ?
C8 C13 1.4022(18) . ?
C9 C10 1.3758(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.3918(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.3931(18) . ?
C12 C13 1.3683(19) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O3 C21 1.2217(16) . ?
O4 C25 1.3632(17) . ?
O4 C28 1.428(2) . ?
C15 C16 1.3878(19) . ?
C15 C20 1.3941(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.4946(19) . ?
C21 C22 1.4900(19) . ?
C22 C27 1.3905(19) . ?
C22 C23 1.3979(18) . ?
C23 C24 1.3744(19) . ?
C23 H23 0.9300 . ?
C24 C25 1.3865(19) . ?
C24 H24 0.9300 . ?
C25 C26 1.3875(19) . ?
C26 C27 1.3783(19) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?

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
C11 O2 C14 118.00(11) . . ?
C2 C1 C6 120.25(14) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.07(15) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.28(15) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.94(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.42(15) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.02(13) . . ?
C1 C6 C7 121.84(12) . . ?
C5 C6 C7 118.96(13) . . ?
O1 C7 C8 120.28(13) . . ?
O1 C7 C6 119.09(14) . . ?
C8 C7 C6 120.63(12) . . ?
C9 C8 C13 117.57(12) . . ?
C9 C8 C7 119.17(12) . . ?
C13 C8 C7 123.17(12) . . ?
C10 C9 C8 121.99(12) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 119.41(12) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
O2 C11 C10 124.54(12) . . ?
O2 C11 C12 116.00(11) . . ?
C10 C11 C12 119.45(13) . . ?
C13 C12 C11 120.57(12) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 120.97(12) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C25 O4 C28 118.06(12) . . ?
C16 C15 C20 120.02(13) . . ?
C16 C15 H15 120.0 . . ?
C20 C15 H15 120.0 . . ?
C17 C16 C15 120.25(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.20(16) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C19 120.14(15) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 120.58(15) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 118.80(13) . . ?
C15 C20 C21 122.18(12) . . ?
C19 C20 C21 118.76(13) . . ?
O3 C21 C22 119.50(13) . . ?
O3 C21 C20 119.69(13) . . ?
C22 C21 C20 120.77(12) . . ?
C27 C22 C23 117.85(12) . . ?
C27 C22 C21 118.73(12) . . ?
C23 C22 C21 123.35(12) . . ?
C24 C23 C22 120.91(12) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 120.27(13) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
O4 C25 C24 115.56(12) . . ?
O4 C25 C26 124.69(12) . . ?
C24 C25 C26 119.74(13) . . ?
C27 C26 C25 119.50(13) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C22 121.67(12) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
O4 C28 H28A 109.5 . . ?
O4 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
O4 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C6 C1 C2 C3 1.5(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
C2 C1 C6 C7 174.25(14) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 -175.64(14) . . . . ?
C1 C6 C7 O1 -139.13(16) . . . . ?
C5 C6 C7 O1 35.9(2) . . . . ?
C1 C6 C7 C8 40.7(2) . . . . ?
C5 C6 C7 C8 -144.35(14) . . . . ?
O1 C7 C8 C9 18.9(2) . . . . ?
C6 C7 C8 C9 -160.89(13) . . . . ?
O1 C7 C8 C13 -157.53(15) . . . . ?
C6 C7 C8 C13 22.7(2) . . . . ?
C13 C8 C9 C10 -1.9(2) . . . . ?
C7 C8 C9 C10 -178.52(13) . . . . ?
C8 C9 C10 C11 1.1(2) . . . . ?
C14 O2 C11 C10 -2.4(2) . . . . ?
C14 O2 C11 C12 178.43(13) . . . . ?
C9 C10 C11 O2 -178.36(12) . . . . ?
C9 C10 C11 C12 0.8(2) . . . . ?
O2 C11 C12 C13 177.31(12) . . . . ?
C10 C11 C12 C13 -1.9(2) . . . . ?
C11 C12 C13 C8 1.1(2) . . . . ?
C9 C8 C13 C12 0.7(2) . . . . ?
C7 C8 C13 C12 177.23(13) . . . . ?
C20 C15 C16 C17 0.5(2) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C16 C15 C20 C19 -0.5(2) . . . . ?
C16 C15 C20 C21 173.62(13) . . . . ?
C18 C19 C20 C15 0.1(2) . . . . ?
C18 C19 C20 C21 -174.19(14) . . . . ?
C15 C20 C21 O3 -151.57(14) . . . . ?
C19 C20 C21 O3 22.6(2) . . . . ?
C15 C20 C21 C22 26.18(19) . . . . ?
C19 C20 C21 C22 -159.69(13) . . . . ?
O3 C21 C22 C27 31.33(19) . . . . ?
C20 C21 C22 C27 -146.43(13) . . . . ?
O3 C21 C22 C23 -145.51(14) . . . . ?
C20 C21 C22 C23 36.73(18) . . . . ?
C27 C22 C23 C24 0.20(18) . . . . ?
C21 C22 C23 C24 177.06(12) . . . . ?
C22 C23 C24 C25 1.90(19) . . . . ?
C28 O4 C25 C24 179.01(14) . . . . ?
C28 O4 C25 C26 -0.8(2) . . . . ?
C23 C24 C25 O4 177.94(11) . . . . ?
C23 C24 C25 C26 -2.27(19) . . . . ?
O4 C25 C26 C27 -179.70(12) . . . . ?
C24 C25 C26 C27 0.54(19) . . . . ?
C25 C26 C27 C22 1.6(2) . . . . ?
C23 C22 C27 C26 -1.96(19) . . . . ?
C21 C22 C27 C26 -178.98(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C14 H14B O1 0.96 2.57 3.479(2) 158.5 2_756

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4



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

data_ddz20170
_database_code_depnum_ccdc_archive 'CCDC 2463840'
loop_
_audit_author_name
_audit_author_address
'Dan wang'
;WENZHOU UNIVERSITY
China
;
_audit_update_record             
;
2025-06-12 deposited with the CCDC.	2025-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.1091(3)
_cell_length_b                   7.9865(2)
_cell_length_c                   12.5911(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.6440(10)
_cell_angle_gamma                90
_cell_volume                     1225.29(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4637
_cell_measurement_theta_min      6.176
_cell_measurement_theta_max      52.963

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11977
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.088
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2390
_reflns_number_gt                1893
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.2289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.093(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2390
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.77134(10) 0.5836(2) 0.20598(10) 0.0879(5) Uani 1 1 d . . . . .
N1 N 0.39620(10) 0.66202(17) 0.40608(11) 0.0627(4) Uani 1 1 d . . . . .
C1 C 0.95123(14) 0.7944(2) 0.32404(15) 0.0718(5) Uani 1 1 d . . . . .
H1 H 0.9235 0.8102 0.2453 0.086 Uiso 1 1 calc R U . . .
C2 C 1.05348(15) 0.8568(3) 0.38884(18) 0.0842(6) Uani 1 1 d . . . . .
H2 H 1.0936 0.9165 0.3541 0.101 Uiso 1 1 calc R U . . .
C3 C 1.09588(15) 0.8305(3) 0.50482(18) 0.0823(6) Uani 1 1 d . . . . .
H3 H 1.1648 0.8724 0.5485 0.099 Uiso 1 1 calc R U . . .
C4 C 1.03728(14) 0.7431(2) 0.55629(15) 0.0751(5) Uani 1 1 d . . . . .
H4 H 1.0670 0.7240 0.6346 0.090 Uiso 1 1 calc R U . . .
C5 C 0.93409(13) 0.6830(2) 0.49236(13) 0.0623(4) Uani 1 1 d . . . . .
H5 H 0.8942 0.6251 0.5282 0.075 Uiso 1 1 calc R U . . .
C6 C 0.88921(12) 0.70817(19) 0.37487(12) 0.0559(4) Uani 1 1 d . . . . .
C7 C 0.78061(13) 0.6397(2) 0.29999(12) 0.0589(4) Uani 1 1 d . . . . .
C8 C 0.68525(11) 0.64301(17) 0.33511(11) 0.0507(4) Uani 1 1 d . . . . .
C9 C 0.59144(13) 0.55398(19) 0.27087(12) 0.0593(4) Uani 1 1 d . . . . .
H9 H 0.5929 0.4890 0.2102 0.071 Uiso 1 1 calc R U . . .
C10 C 0.49730(12) 0.5584(2) 0.29355(12) 0.0599(4) Uani 1 1 d . . . . .
H10 H 0.4367 0.4965 0.2484 0.072 Uiso 1 1 calc R U . . .
C11 C 0.49043(11) 0.65481(17) 0.38400(11) 0.0503(4) Uani 1 1 d . . . . .
C12 C 0.58543(11) 0.74366(17) 0.45029(11) 0.0519(4) Uani 1 1 d . . . . .
H12 H 0.5847 0.8075 0.5118 0.062 Uiso 1 1 calc R U . . .
C13 C 0.67904(12) 0.73766(18) 0.42583(12) 0.0521(4) Uani 1 1 d . . . . .
H13 H 0.7402 0.7984 0.4710 0.062 Uiso 1 1 calc R U . . .
C14 C 0.29613(14) 0.5832(3) 0.33161(17) 0.0884(6) Uani 1 1 d . . . . .
H14A H 0.2749 0.6302 0.2564 0.133 Uiso 1 1 calc R U . . .
H14B H 0.2390 0.6020 0.3608 0.133 Uiso 1 1 calc R U . . .
H14C H 0.3080 0.4650 0.3283 0.133 Uiso 1 1 calc R U . . .
C15 C 0.38775(15) 0.7619(2) 0.49761(15) 0.0748(5) Uani 1 1 d . . . . .
H15A H 0.4533 0.7490 0.5643 0.112 Uiso 1 1 calc R U . . .
H15B H 0.3255 0.7258 0.5145 0.112 Uiso 1 1 calc R U . . .
H15C H 0.3788 0.8775 0.4751 0.112 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 C7 1.2291(17) . ?
N1 C11 1.3639(18) . ?
N1 C15 1.439(2) . ?
N1 C14 1.445(2) . ?
C1 C2 1.380(2) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(2) . ?
C7 C8 1.472(2) . ?
C8 C9 1.392(2) . ?
C8 C13 1.3970(19) . ?
C9 C10 1.366(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.4087(19) . ?
C12 C13 1.372(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C11 N1 C15 121.99(13) . . ?
C11 N1 C14 121.53(14) . . ?
C15 N1 C14 116.20(14) . . ?
C2 C1 C6 120.84(16) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.83(17) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 120.32(18) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.20(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.61(16) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.18(15) . . ?
C1 C6 C7 118.36(14) . . ?
C5 C6 C7 123.38(14) . . ?
O1 C7 C8 120.17(14) . . ?
O1 C7 C6 118.35(13) . . ?
C8 C7 C6 121.46(12) . . ?
C9 C8 C13 116.49(13) . . ?
C9 C8 C7 118.84(13) . . ?
C13 C8 C7 124.57(13) . . ?
C10 C9 C8 122.55(13) . . ?
C10 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C9 C10 C11 121.09(14) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
N1 C11 C10 121.47(13) . . ?
N1 C11 C12 121.82(13) . . ?
C10 C11 C12 116.72(13) . . ?
C13 C12 C11 121.19(13) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C8 121.95(13) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C6 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C2 C1 C6 C7 -178.37(16) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C4 C5 C6 C7 176.98(15) . . . . ?
C1 C6 C7 O1 36.6(2) . . . . ?
C5 C6 C7 O1 -140.04(17) . . . . ?
C1 C6 C7 C8 -141.59(15) . . . . ?
C5 C6 C7 C8 41.8(2) . . . . ?
O1 C7 C8 C9 12.1(2) . . . . ?
C6 C7 C8 C9 -169.79(13) . . . . ?
O1 C7 C8 C13 -164.15(15) . . . . ?
C6 C7 C8 C13 14.0(2) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
C7 C8 C9 C10 -176.06(14) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C15 N1 C11 C10 -179.26(14) . . . . ?
C14 N1 C11 C10 -5.6(2) . . . . ?
C15 N1 C11 C12 0.6(2) . . . . ?
C14 N1 C11 C12 174.22(15) . . . . ?
C9 C10 C11 N1 178.92(14) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
N1 C11 C12 C13 -178.80(13) . . . . ?
C10 C11 C12 C13 1.1(2) . . . . ?
C11 C12 C13 C8 -0.4(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C7 C8 C13 C12 175.96(14) . . . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.024

_shelxl_version_number           2013-4



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

data_mo_ddz20107_0m
_database_code_depnum_ccdc_archive 'CCDC 2159960'
loop_
_audit_author_name
_audit_author_address
bpo
;Wenzhou university
China
;
_audit_update_record             
;
2022-03-18 deposited with the CCDC.	2025-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 O'
_chemical_formula_weight         182.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   7.9842(16)
_cell_length_b                   10.281(2)
_cell_length_c                   12.1164(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     994.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3931
_cell_measurement_theta_min      6.111
_cell_measurement_theta_max      53.068

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8854
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.055
_diffrn_reflns_theta_max         25.962
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1928
_reflns_number_gt                1670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.993

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.0532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.26(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 619 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.1(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1928
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2903(3) 0.73538(18) 0.81388(12) 0.0936(7) Uani 1 1 d . . . . .
C1 C 0.3999(3) 0.9057(2) 0.64831(19) 0.0657(6) Uani 1 1 d . . . . .
H1 H 0.4539 0.9141 0.7159 0.079 Uiso 1 1 calc R U . . .
C2 C 0.4183(4) 1.0009(2) 0.5702(2) 0.0758(7) Uani 1 1 d . . . . .
H2 H 0.4862 1.0725 0.5843 0.091 Uiso 1 1 calc R U . . .
C3 C 0.3363(4) 0.9905(2) 0.4709(2) 0.0758(7) Uani 1 1 d . . . . .
H3 H 0.3476 1.0558 0.4183 0.091 Uiso 1 1 calc R U . . .
C4 C 0.2373(3) 0.8835(2) 0.44914(17) 0.0674(7) Uani 1 1 d . . . . .
H4 H 0.1817 0.8769 0.3819 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2207(3) 0.7861(2) 0.52704(16) 0.0575(6) Uani 1 1 d . . . . .
H5 H 0.1553 0.7134 0.5118 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3018(3) 0.79701(19) 0.62802(16) 0.0521(5) Uani 1 1 d . . . . .
C7 C 0.2797(3) 0.7004(2) 0.71814(16) 0.0599(6) Uani 1 1 d . . . . .
C8 C 0.2440(3) 0.5609(2) 0.69319(15) 0.0543(5) Uani 1 1 d . . . . .
C9 C 0.3060(3) 0.4979(2) 0.60080(16) 0.0594(6) Uani 1 1 d . . . . .
H9 H 0.3659 0.5446 0.5482 0.071 Uiso 1 1 calc R U . . .
C10 C 0.2795(4) 0.3663(2) 0.58617(19) 0.0720(7) Uani 1 1 d . . . . .
H10 H 0.3231 0.3245 0.5244 0.086 Uiso 1 1 calc R U . . .
C11 C 0.1895(4) 0.2971(2) 0.6620(2) 0.0791(8) Uani 1 1 d . . . . .
H11 H 0.1710 0.2087 0.6515 0.095 Uiso 1 1 calc R U . . .
C12 C 0.1264(3) 0.3582(3) 0.7537(2) 0.0795(8) Uani 1 1 d . . . . .
H12 H 0.0648 0.3108 0.8050 0.095 Uiso 1 1 calc R U . . .
C13 C 0.1536(3) 0.4889(2) 0.77026(18) 0.0663(6) Uani 1 1 d . . . . .
H13 H 0.1115 0.5293 0.8331 0.080 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 C7 1.217(2) . ?
C1 C2 1.370(3) . ?
C1 C6 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(3) . ?
C7 C8 1.493(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.393(3) . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.9(2) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.99(19) . . ?
C1 C6 C7 118.39(19) . . ?
C5 C6 C7 122.53(18) . . ?
O1 C7 C6 119.6(2) . . ?
O1 C7 C8 119.32(19) . . ?
C6 C7 C8 121.04(16) . . ?
C9 C8 C13 118.6(2) . . ?
C9 C8 C7 123.01(19) . . ?
C13 C8 C7 118.25(19) . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.2(2) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 -176.9(2) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 175.6(2) . . . . ?
C1 C6 C7 O1 27.0(3) . . . . ?
C5 C6 C7 O1 -149.3(2) . . . . ?
C1 C6 C7 C8 -153.2(2) . . . . ?
C5 C6 C7 C8 30.5(3) . . . . ?
O1 C7 C8 C9 -147.5(2) . . . . ?
C6 C7 C8 C9 32.7(3) . . . . ?
O1 C7 C8 C13 28.1(3) . . . . ?
C6 C7 C8 C13 -151.7(2) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 175.1(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C8 0.8(4) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C7 C8 C13 C12 -176.2(2) . . . . ?

_refine_diff_density_max         0.103
_refine_diff_density_min         -0.090
_refine_diff_density_rms         0.020

_shelxl_version_number           2013-4



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

data_mo_dd21008_0m
_database_code_depnum_ccdc_archive 'CCDC 2463839'
loop_
_audit_author_name
_audit_author_address
'Dan wang'
;WENZHOU UNIVERSITY
China
;
_audit_update_record             
;
2025-06-12 deposited with the CCDC.	2025-11-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H9 F O'
_chemical_formula_weight         200.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   6.1578(9)
_cell_length_b                   22.065(3)
_cell_length_c                   7.5440(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.308(5)
_cell_angle_gamma                90
_cell_volume                     1025.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2698
_cell_measurement_theta_min      6.543
_cell_measurement_theta_max      49.732

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6338
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9853
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.854
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1997
_reflns_number_gt                1326
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.1943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.058(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1997
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1614(4) 0.02985(9) 0.4459(4) 0.0925(8) Uani 0.5 1 d . . P A 1
O1 O 0.7633(2) 0.25284(6) 0.4434(2) 0.0930(6) Uani 1 1 d . . . . .
C1 C 0.2432(3) 0.18581(9) 0.3759(2) 0.0604(5) Uani 1 1 d . . . . .
H1 H 0.1700 0.2186 0.3265 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1490(3) 0.12921(10) 0.3729(3) 0.0710(6) Uani 1 1 d . . . . .
H2 H 0.0137 0.1238 0.3199 0.085 Uiso 1 1 calc R U . . .
C3 C 0.2550(4) 0.08092(10) 0.4481(3) 0.0771(6) Uani 1 1 d . . . . .
C4 C 0.4556(4) 0.08850(9) 0.5271(3) 0.0796(7) Uani 1 1 d . . . . .
H4 H 0.5254 0.0557 0.5798 0.095 Uiso 1 1 calc R U . . .
C5 C 0.5520(3) 0.14470(9) 0.5278(3) 0.0680(6) Uani 1 1 d . . . . .
H5 H 0.6885 0.1496 0.5791 0.082 Uiso 1 1 calc R U . . .
C6 C 0.4469(3) 0.19425(8) 0.4523(2) 0.0550(5) Uani 1 1 d . . . . .
C7 C 0.5646(3) 0.25293(8) 0.4464(2) 0.0608(5) Uani 1 1 d . . . . .
C8 C 0.4476(3) 0.31204(8) 0.4446(2) 0.0559(5) Uani 1 1 d . . . . .
C9 C 0.5530(3) 0.36195(9) 0.3736(3) 0.0679(6) Uani 1 1 d . . . . .
H9 H 0.6891 0.3572 0.3225 0.082 Uiso 1 1 calc R U . . .
C10 C 0.4584(4) 0.41822(10) 0.3779(3) 0.0811(7) Uani 1 1 d . . . . .
H10 H 0.5282 0.4514 0.3280 0.097 Uiso 1 1 calc R U . . .
C11 C 0.2596(4) 0.42487(10) 0.4566(3) 0.0810(7) Uani 1 1 d . . . . .
C12 C 0.1515(3) 0.37657(10) 0.5283(3) 0.0737(6) Uani 1 1 d . . . . .
H12 H 0.0165 0.3820 0.5808 0.088 Uiso 1 1 calc R U . . .
C13 C 0.2448(3) 0.31999(9) 0.5218(2) 0.0616(5) Uani 1 1 d . . . . .
H13 H 0.1720 0.2869 0.5692 0.074 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.266(3) . ?
F1' C11 1.266(3) . ?
O1 C7 1.224(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.390(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.485(2) . ?
C7 C8 1.490(2) . ?
C8 C9 1.387(2) . ?
C8 C13 1.392(2) . ?
C9 C10 1.372(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.49(17) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 119.89(19) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
F1 C3 C2 118.1(2) . . ?
F1 C3 C4 121.4(2) . . ?
C2 C3 C4 120.5(2) . . ?
C5 C4 C3 119.80(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.51(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.76(17) . . ?
C1 C6 C7 122.94(16) . . ?
C5 C6 C7 118.17(16) . . ?
O1 C7 C6 119.16(16) . . ?
O1 C7 C8 118.99(16) . . ?
C6 C7 C8 121.85(15) . . ?
C9 C8 C13 118.94(17) . . ?
C9 C8 C7 118.12(16) . . ?
C13 C8 C7 122.78(16) . . ?
C10 C9 C8 120.66(19) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.1(2) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
F1' C11 C12 116.6(3) . . ?
F1' C11 C10 121.6(3) . . ?
C12 C11 C10 121.7(2) . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C12 C13 C8 120.37(18) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 F1 178.6(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
F1 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C6 C7 174.74(17) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 -176.08(18) . . . . ?
C1 C6 C7 O1 -148.83(19) . . . . ?
C5 C6 C7 O1 26.9(3) . . . . ?
C1 C6 C7 C8 31.4(3) . . . . ?
C5 C6 C7 C8 -152.90(17) . . . . ?
O1 C7 C8 C9 24.2(3) . . . . ?
C6 C7 C8 C9 -156.05(17) . . . . ?
O1 C7 C8 C13 -151.29(18) . . . . ?
C6 C7 C8 C13 28.5(3) . . . . ?
C13 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C10 -176.14(18) . . . . ?
C8 C9 C10 C11 1.3(3) . . . . ?
C9 C10 C11 F1' -178.6(2) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
F1' C11 C12 C13 177.8(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C7 C8 C13 C12 174.98(17) . . . . ?

_refine_diff_density_max         0.139
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.025

_shelxl_version_number           2013-4



