# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc2lykgl
_database_code_depnum_ccdc_archive 'CCDC 2411690'
loop_
_audit_author_name
_audit_author_address
FDW
;TaiZhou University
China
;
_audit_update_record             
;
2024-12-19 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;
_audit_creation_date             2024-10-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 F N O3'
_chemical_formula_sum            'C10 H12 F N O3'
_chemical_formula_weight         213.21
_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'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.00400(10)
_cell_length_b                   9.2021(2)
_cell_length_c                   12.2894(3)
_cell_angle_alpha                71.3050(10)
_cell_angle_beta                 80.8100(10)
_cell_angle_gamma                83.8480(10)
_cell_volume                     528.21(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4642
_cell_measurement_temperature    655(2)
_cell_measurement_theta_max      68.137
_cell_measurement_theta_min      5.338
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.812
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5775
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1110 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.7668.
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    1.341
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6753
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.227
_diffrn_reflns_theta_min         5.338
_diffrn_ambient_temperature      655.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1716
_reflns_number_total             1864
_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       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_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     139
_refine_ls_number_reflns         1864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0482
_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)+(0.0757P)²+0.1104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1355
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_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
F1 F 0.5621(2) 0.85092(12) 0.45401(9) 0.0683(4) Uani 1 1 d . . . . .
O1 O 0.7890(3) 0.84683(14) 0.64632(11) 0.0640(4) Uani 1 1 d . . . . .
O3 O 0.1877(2) 0.66713(13) 0.40914(9) 0.0592(4) Uani 1 1 d . . . . .
N1 N 0.1864(3) 0.53382(14) 0.60433(10) 0.0476(3) Uani 1 1 d . . . . .
H1 H 0.076562 0.464772 0.610999 0.057 Uiso 1 1 calc R . . . .
O2 O 0.6128(4) 0.6977(2) 0.81781(12) 0.0931(6) Uani 1 1 d . . . . .
C3 C 0.4792(3) 0.67633(17) 0.64733(13) 0.0456(4) Uani 1 1 d . . . . .
C4 C 0.4506(3) 0.73192(17) 0.53481(14) 0.0484(4) Uani 1 1 d . . . . .
C6 C 0.3083(3) 0.54450(17) 0.69688(13) 0.0457(4) Uani 1 1 d . . . . .
C5 C 0.2609(3) 0.64385(17) 0.50415(13) 0.0465(4) Uani 1 1 d . . . . .
C2 C 0.6315(3) 0.73846(19) 0.71477(14) 0.0510(4) Uani 1 1 d . . . . .
C7 C 0.2705(4) 0.4508(2) 0.80482(14) 0.0563(4) Uani 1 1 d . . . . .
H7 H 0.359853 0.470800 0.858819 0.068 Uiso 1 1 calc R . . . .
C8 C 0.0971(4) 0.3158(2) 0.84750(15) 0.0680(6) Uani 1 1 d . . . . .
H8 H -0.030375 0.328295 0.791906 0.082 Uiso 1 1 calc R . . . .
C1 C 0.9249(5) 0.9276(2) 0.7029(2) 0.0736(6) Uani 1 1 d . . . . .
H1A H 1.042642 0.998631 0.645911 0.110 Uiso 1 1 calc GR . . . .
H1B H 1.029734 0.855121 0.757492 0.110 Uiso 1 1 calc GR . . . .
H1C H 0.792465 0.982878 0.742777 0.110 Uiso 1 1 calc GR . . . .
C9 C -0.0657(5) 0.3105(3) 0.96441(19) 0.0879(7) Uani 1 1 d . . . . .
H9A H 0.056031 0.296404 1.020441 0.132 Uiso 1 1 calc GR . . . .
H9B H -0.182582 0.226494 0.989136 0.132 Uiso 1 1 calc GR . . . .
H9C H -0.173036 0.405179 0.957339 0.132 Uiso 1 1 calc GR . . . .
C10 C 0.2733(8) 0.1694(3) 0.8531(3) 0.1200(11) Uani 1 1 d . . . . .
H10A H 0.378364 0.179115 0.778837 0.180 Uiso 1 1 calc GR . . . .
H10B H 0.160129 0.084173 0.873570 0.180 Uiso 1 1 calc GR . . . .
H10C H 0.392798 0.152133 0.910413 0.180 Uiso 1 1 calc GR . . . .


_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 C4 1.3241(17) . ?
O1 C2 1.320(2) . ?
O1 C1 1.445(2) . ?
O3 C5 1.2260(18) . ?
N1 H1 0.8600 . ?
N1 C6 1.4077(19) . ?
N1 C5 1.3473(19) . ?
O2 C2 1.191(2) . ?
C3 C4 1.337(2) . ?
C3 C6 1.468(2) . ?
C3 C2 1.481(2) . ?
C4 C5 1.475(2) . ?
C6 C7 1.327(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.496(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.523(3) . ?
C8 C10 1.518(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C2 O1 C1 116.33(15) . . ?
C6 N1 H1 123.8 . . ?
C5 N1 H1 123.8 . . ?
C5 N1 C6 112.47(12) . . ?
C4 C3 C6 106.45(13) . . ?
C4 C3 C2 128.55(14) . . ?
C6 C3 C2 124.82(14) . . ?
F1 C4 C3 129.18(15) . . ?
F1 C4 C5 119.45(14) . . ?
C3 C4 C5 111.36(13) . . ?
N1 C6 C3 105.60(12) . . ?
C7 C6 N1 125.04(14) . . ?
C7 C6 C3 129.36(14) . . ?
O3 C5 N1 128.39(14) . . ?
O3 C5 C4 127.50(14) . . ?
N1 C5 C4 104.11(13) . . ?
O1 C2 C3 111.49(14) . . ?
O2 C2 O1 123.90(15) . . ?
O2 C2 C3 124.60(15) . . ?
C6 C7 H7 117.1 . . ?
C6 C7 C8 125.88(15) . . ?
C8 C7 H7 117.1 . . ?
C7 C8 H8 108.3 . . ?
C7 C8 C9 110.21(17) . . ?
C7 C8 C10 109.65(19) . . ?
C9 C8 H8 108.3 . . ?
C10 C8 H8 108.3 . . ?
C10 C8 C9 112.1(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_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_a
_database_code_depnum_ccdc_archive 'CCDC 2411565'
loop_
_audit_author_name
_audit_author_address
'xiao geng'
;Taizhou University
China
;
_audit_update_record             
;
2024-12-19 deposited with the CCDC.	2025-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N O5'
_chemical_formula_weight         331.36

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.385(6)
_cell_length_b                   10.583(8)
_cell_length_c                   11.061(8)
_cell_angle_alpha                104.306(12)
_cell_angle_beta                 104.375(12)
_cell_angle_gamma                105.172(11)
_cell_volume                     865.0(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1131
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      23.17

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4163
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_sigmaI/netI    0.0705
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2998
_reflns_number_gt                1720
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1561
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3274(3) 0.9147(2) 0.0986(2) 0.0524(6) Uani 1 1 d . . .
O2 O 0.5750(3) 0.8599(2) 0.1357(3) 0.0693(8) Uani 1 1 d . . .
C12 C 0.2638(4) 0.5729(3) 0.0595(3) 0.0451(8) Uani 1 1 d . . .
O4 O 0.3524(3) 0.7333(2) 0.2778(3) 0.0694(7) Uani 1 1 d . . .
N1 N 0.1669(3) 0.3582(3) -0.1312(3) 0.0503(7) Uani 1 1 d . . .
O5 O 0.2763(4) 0.5042(3) 0.2456(3) 0.0891(10) Uani 1 1 d . . .
C6 C 0.2056(4) 1.1422(3) 0.2262(4) 0.0513(9) Uani 1 1 d . . .
O3 O 0.2364(4) 0.6664(2) -0.1167(3) 0.0722(8) Uani 1 1 d . . .
C11 C 0.2961(4) 0.6796(3) 0.0013(4) 0.0488(8) Uani 1 1 d . . .
C13 C 0.1735(4) 0.4301(3) -0.0144(4) 0.0495(8) Uani 1 1 d . . .
H13A H 0.1091 0.3800 0.0264 0.059 Uiso 1 1 calc R . .
C8 C 0.4282(5) 1.0626(3) 0.1723(4) 0.0610(10) Uani 1 1 d . . .
H8A H 0.5382 1.0935 0.1546 0.073 Uiso 1 1 calc R . .
C1 C 0.2947(5) 1.1162(3) 0.3363(4) 0.0550(9) Uani 1 1 d . . .
C10 C 0.4172(5) 0.8268(3) 0.0909(4) 0.0506(9) Uani 1 1 d . . .
C14 C 0.3003(5) 0.6148(4) 0.2023(4) 0.0575(9) Uani 1 1 d . . .
C5 C 0.0486(5) 1.1661(3) 0.2177(4) 0.0634(10) Uani 1 1 d . . .
H5A H -0.0119 1.1817 0.1433 0.076 Uiso 1 1 calc R . .
C16 C 0.0467(5) 0.2130(3) -0.1944(4) 0.0646(10) Uani 1 1 d . . .
H16A H -0.0215 0.1901 -0.1398 0.097 Uiso 1 1 calc R . .
H16B H 0.1135 0.1524 -0.2048 0.097 Uiso 1 1 calc R . .
H16C H -0.0301 0.2018 -0.2796 0.097 Uiso 1 1 calc R . .
C7 C 0.3051(5) 1.1391(4) 0.1297(4) 0.0649(10) Uani 1 1 d . . .
H7A H 0.3705 1.2323 0.1364 0.078 Uiso 1 1 calc R . .
H7B H 0.2263 1.0895 0.0395 0.078 Uiso 1 1 calc R . .
C4 C -0.0165(5) 1.1665(4) 0.3202(5) 0.0725(11) Uani 1 1 d . . .
H4A H -0.1212 1.1831 0.3149 0.087 Uiso 1 1 calc R . .
C9 C 0.4578(5) 1.0883(4) 0.3198(4) 0.0668(11) Uani 1 1 d . . .
H9A H 0.4680 1.0076 0.3431 0.080 Uiso 1 1 calc R . .
H9B H 0.5627 1.1678 0.3739 0.080 Uiso 1 1 calc R . .
C15 C 0.2801(5) 0.4075(4) -0.2031(4) 0.0658(10) Uani 1 1 d . . .
H15A H 0.3539 0.5022 -0.1541 0.099 Uiso 1 1 calc R . .
H15B H 0.2093 0.4018 -0.2884 0.099 Uiso 1 1 calc R . .
H15C H 0.3516 0.3509 -0.2141 0.099 Uiso 1 1 calc R . .
C2 C 0.2290(6) 1.1181(4) 0.4399(4) 0.0730(11) Uani 1 1 d . . .
H2A H 0.2892 1.1031 0.5147 0.088 Uiso 1 1 calc R . .
C3 C 0.0709(6) 1.1428(4) 0.4305(5) 0.0787(12) Uani 1 1 d . . .
H3A H 0.0250 1.1432 0.4989 0.094 Uiso 1 1 calc R . .
C17 C 0.3144(6) 0.5320(5) 0.3936(5) 0.0937(15) Uani 1 1 d . . .
H17A H 0.3323 0.4532 0.4173 0.112 Uiso 1 1 calc R . .
H17B H 0.4178 0.6137 0.4445 0.112 Uiso 1 1 calc R . .
C18 C 0.1612(7) 0.5537(5) 0.4166(6) 0.1131(18) Uani 1 1 d . . .
H18A H 0.1754 0.5724 0.5088 0.170 Uiso 1 1 calc R . .
H18B H 0.0605 0.4719 0.3649 0.170 Uiso 1 1 calc R . .
H18C H 0.1451 0.6312 0.3914 0.170 Uiso 1 1 calc R . .


_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 C10 1.341(4) . ?
O1 C8 1.470(4) . ?
O2 C10 1.211(4) . ?
C12 C13 1.417(4) . ?
C12 C11 1.431(4) . ?
C12 C14 1.459(5) . ?
O4 C14 1.214(4) . ?
N1 C13 1.307(4) . ?
N1 C15 1.458(4) . ?
N1 C16 1.475(4) . ?
O5 C14 1.357(4) . ?
O5 C17 1.524(5) . ?
C6 C5 1.390(5) . ?
C6 C1 1.392(5) . ?
C6 C7 1.508(5) . ?
O3 C11 1.234(4) . ?
C11 C10 1.533(5) . ?
C13 H13A 0.9300 . ?
C8 C7 1.525(5) . ?
C8 C9 1.530(5) . ?
C8 H8A 0.9800 . ?
C1 C2 1.388(5) . ?
C1 C9 1.516(5) . ?
C5 C4 1.375(5) . ?
C5 H5A 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C4 C3 1.375(6) . ?
C4 H4A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C2 C3 1.402(6) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C17 C18 1.433(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C10 O1 C8 117.3(3) . . ?
C13 C12 C11 123.9(3) . . ?
C13 C12 C14 117.3(3) . . ?
C11 C12 C14 118.0(3) . . ?
C13 N1 C15 124.7(3) . . ?
C13 N1 C16 119.5(3) . . ?
C15 N1 C16 115.6(3) . . ?
C14 O5 C17 118.0(3) . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 C7 129.6(3) . . ?
C1 C6 C7 110.0(3) . . ?
O3 C11 C12 126.7(3) . . ?
O3 C11 C10 114.6(3) . . ?
C12 C11 C10 118.7(3) . . ?
N1 C13 C12 129.8(3) . . ?
N1 C13 H13A 115.1 . . ?
C12 C13 H13A 115.1 . . ?
O1 C8 C7 105.0(3) . . ?
O1 C8 C9 108.8(3) . . ?
C7 C8 C9 105.7(3) . . ?
O1 C8 H8A 112.3 . . ?
C7 C8 H8A 112.3 . . ?
C9 C8 H8A 112.3 . . ?
C2 C1 C6 119.8(4) . . ?
C2 C1 C9 129.8(4) . . ?
C6 C1 C9 110.4(3) . . ?
O2 C10 O1 125.3(3) . . ?
O2 C10 C11 123.4(3) . . ?
O1 C10 C11 110.8(3) . . ?
O4 C14 O5 122.0(4) . . ?
O4 C14 C12 126.1(3) . . ?
O5 C14 C12 111.9(3) . . ?
C4 C5 C6 119.3(4) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C7 C8 103.5(3) . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C8 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C1 C9 C8 103.2(3) . . ?
C1 C9 H9A 111.1 . . ?
C8 C9 H9A 111.1 . . ?
C1 C9 H9B 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
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 . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C18 C17 O5 104.4(4) . . ?
C18 C17 H17A 110.9 . . ?
O5 C17 H17A 110.9 . . ?
C18 C17 H17B 110.9 . . ?
O5 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.055
