# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2234688'
loop_
_audit_author_name
_audit_author_address
'Li Tao'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 O4'
_chemical_formula_weight         222.23

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   5.8827(3)
_cell_length_b                   24.9167(9)
_cell_length_c                   8.1339(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.1490(10)
_cell_angle_gamma                90.00
_cell_volume                     1119.28(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5888
_cell_measurement_theta_min      3.6256
_cell_measurement_theta_max      27.4985

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8018
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1951
_reflns_number_gt                1785
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0392P)²+0.6992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1951
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O4 O 0.06715(19) 0.04340(4) 0.18868(14) 0.0293(3) Uani 1 1 d . . .
O2 O -0.91440(19) 0.11625(5) -0.22823(14) 0.0313(3) Uani 1 1 d . . .
O3 O -0.2627(2) 0.02456(5) 0.25413(16) 0.0391(3) Uani 1 1 d . . .
O1 O -0.6003(2) 0.12417(6) -0.32009(15) 0.0414(3) Uani 1 1 d . . .
C9 C -0.6801(3) 0.11311(6) -0.20798(19) 0.0243(3) Uani 1 1 d . . .
C11 C -0.1713(3) 0.04296(6) 0.1557(2) 0.0251(3) Uani 1 1 d . . .
C12 C 0.2150(3) 0.02092(7) 0.3552(2) 0.0313(4) Uani 1 1 d . . .
H12A H 0.3860 0.0229 0.3664 0.047 Uiso 1 1 calc R . .
H12B H 0.1698 -0.0167 0.3617 0.047 Uiso 1 1 calc R . .
H12C H 0.1893 0.0413 0.4505 0.047 Uiso 1 1 calc R . .
C3 C -0.4638(3) 0.14700(6) 0.09380(19) 0.0266(4) Uani 1 1 d . . .
C2 C -0.5298(3) 0.09679(6) -0.02171(19) 0.0259(3) Uani 1 1 d . . .
H2A H -0.6311 0.0730 0.0242 0.031 Uiso 1 1 calc R . .
C1 C -0.3083(3) 0.06512(7) -0.0222(2) 0.0288(4) Uani 1 1 d . . .
H1A H -0.3605 0.0352 -0.1072 0.035 Uiso 1 1 calc R . .
H1B H -0.2006 0.0888 -0.0601 0.035 Uiso 1 1 calc R . .
C10 C -1.0741(3) 0.13456(7) -0.3984(2) 0.0330(4) Uani 1 1 d . . .
H10A H -1.2410 0.1357 -0.3992 0.049 Uiso 1 1 calc R . .
H10B H -1.0642 0.1098 -0.4892 0.049 Uiso 1 1 calc R . .
H10C H -1.0250 0.1705 -0.4215 0.049 Uiso 1 1 calc R . .
C8 C -0.2827(3) 0.18235(7) 0.0884(2) 0.0334(4) Uani 1 1 d . . .
H8A H -0.1951 0.1754 0.0120 0.040 Uiso 1 1 calc R . .
C4 C -0.5898(3) 0.15839(6) 0.2050(2) 0.0307(4) Uani 1 1 d . . .
H4A H -0.7139 0.1347 0.2100 0.037 Uiso 1 1 calc R . .
C7 C -0.2295(3) 0.22783(7) 0.1943(2) 0.0379(4) Uani 1 1 d . . .
H7A H -0.1049 0.2516 0.1907 0.045 Uiso 1 1 calc R . .
C5 C -0.5376(3) 0.20381(7) 0.3091(2) 0.0354(4) Uani 1 1 d . . .
H5A H -0.6266 0.2111 0.3843 0.042 Uiso 1 1 calc R . .
C6 C -0.3575(3) 0.23849(7) 0.3047(2) 0.0371(4) Uani 1 1 d . . .
H6A H -0.3215 0.2695 0.3770 0.045 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
O4 C11 1.3343(18) . ?
O4 C12 1.4470(18) . ?
O2 C9 1.3332(19) . ?
O2 C10 1.4528(18) . ?
O3 C11 1.1985(19) . ?
O1 C9 1.1927(19) . ?
C9 C2 1.523(2) . ?
C11 C1 1.499(2) . ?
C3 C8 1.395(2) . ?
C3 C4 1.382(2) . ?
C3 C2 1.532(2) . ?
C2 C1 1.525(2) . ?
C8 C7 1.392(2) . ?
C4 C5 1.383(2) . ?
C7 C6 1.382(3) . ?
C5 C6 1.377(3) . ?

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 O4 C12 115.85(12) . . ?
C9 O2 C10 115.98(12) . . ?
O1 C9 O2 123.68(14) . . ?
O1 C9 C2 125.16(14) . . ?
O2 C9 C2 111.08(12) . . ?
O3 C11 O4 123.47(14) . . ?
O3 C11 C1 124.75(14) . . ?
O4 C11 C1 111.68(12) . . ?
C8 C3 C4 118.60(15) . . ?
C8 C3 C2 122.10(14) . . ?
C4 C3 C2 119.29(14) . . ?
C9 C2 C3 109.25(12) . . ?
C9 C2 C1 109.82(12) . . ?
C3 C2 C1 112.83(13) . . ?
C11 C1 C2 111.34(13) . . ?
C7 C8 C3 120.39(16) . . ?
C5 C4 C3 120.84(16) . . ?
C8 C7 C6 120.12(16) . . ?
C4 C5 C6 120.52(16) . . ?
C7 C6 C5 119.52(15) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_pl
_database_code_depnum_ccdc_archive 'CCDC 2234689'
loop_
_audit_author_name
_audit_author_address
'Li Tao'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-01-06 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;
_audit_creation_date             2022-04-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O4'
_chemical_formula_sum            'C18 H18 O4'
_chemical_formula_weight         298.32
_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 0.0033 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   5.8450(12)
_cell_length_b                   17.181(3)
_cell_length_c                   7.9441(15)
_cell_angle_alpha                90
_cell_angle_beta                 107.273(5)
_cell_angle_gamma                90
_cell_volume                     761.8(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3055
_cell_measurement_temperature    292.15
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.2730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1825 before and 0.0891 after correction.
The Ratio of minimum to maximum transmission is 0.3661.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_unetI/netI     0.1576
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5821
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.371
_diffrn_ambient_temperature      292.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                795
_reflns_number_total             1343
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2089
_refine_ls_R_factor_gt           0.1231
_refine_ls_restrained_S_all      1.099
_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)+(0.0472P)²+2.2300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2097
_refine_ls_wR_factor_ref         0.2355
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00N(H00N)
2.b Aromatic/amide H refined with riding coordinates:
 C003(H003), C007(H007), C00J(H00J), C00M(H00M), C013(H013)
2.c Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O -0.6469(6) 0.5752(2) -0.2868(5) 0.0574(12) Uani 1 1 d . . . . .
O005 O -0.9710(6) 0.5510(2) -0.2102(4) 0.0510(11) Uani 1 1 d . . . . .
C003 C -0.4035(12) 0.7277(3) 0.3288(7) 0.0544(17) Uani 1 1 d . . . . .
H003 H -0.369844 0.772007 0.399014 0.065 Uiso 1 1 calc R U . . .
C007 C -0.5830(11) 0.6791(4) 0.3380(7) 0.0564(17) Uani 1 1 d . . . . .
H007 H -0.671959 0.690146 0.414564 0.068 Uiso 1 1 calc R U . . .
C009 C -0.5097(12) 0.5976(3) 0.1226(7) 0.0499(16) Uani 1 1 d . . . . .
C00G C -0.7393(9) 0.5508(3) -0.1844(6) 0.0337(12) Uani 1 1 d . . . . .
C00J C -0.3267(12) 0.6459(4) 0.1126(7) 0.0554(17) Uani 1 1 d . . . . .
H00J H -0.238910 0.634517 0.035399 0.066 Uiso 1 1 calc R U . . .
C00K C -1.1189(9) 0.5837(4) -0.3728(7) 0.0536(16) Uani 1 1 d . . . . .
H00A H -1.066414 0.635706 -0.385624 0.080 Uiso 1 1 calc R U . . .
H00B H -1.282562 0.584814 -0.371480 0.080 Uiso 1 1 calc R U . . .
H00C H -1.106373 0.552387 -0.469738 0.080 Uiso 1 1 calc R U . . .
C00M C -0.6321(11) 0.6148(4) 0.2357(7) 0.0560(17) Uani 1 1 d . . . . .
H00M H -0.753938 0.581613 0.244268 0.067 Uiso 1 1 calc R U . . .
C00N C -0.6038(9) 0.5226(4) -0.0035(7) 0.061(2) Uani 1 1 d . . . . .
H00N H -0.711513 0.491884 0.044248 0.073 Uiso 1 1 calc R U . . .
C013 C -0.2735(11) 0.7114(4) 0.2174(8) 0.0568(17) Uani 1 1 d . . . . .
H013 H -0.149453 0.744204 0.211729 0.068 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 C00G 1.179(5) . ?
O005 C00G 1.309(5) . ?
O005 C00K 1.438(6) . ?
C003 H003 0.9300 . ?
C003 C007 1.359(8) . ?
C003 C013 1.355(8) . ?
C007 H007 0.9300 . ?
C007 C00M 1.351(8) . ?
C009 C00J 1.376(8) . ?
C009 C00M 1.337(8) . ?
C009 C00N 1.624(8) . ?
C00G C00N 1.500(7) . ?
C00J H00J 0.9300 . ?
C00J C013 1.379(8) . ?
C00K H00A 0.9600 . ?
C00K H00B 0.9600 . ?
C00K H00C 0.9600 . ?
C00M H00M 0.9300 . ?
C00N C00N 1.429(11) 3_465 ?
C00N H00N 0.9800 . ?
C013 H013 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
C00G O005 C00K 117.4(4) . . ?
C007 C003 H003 120.0 . . ?
C013 C003 H003 120.0 . . ?
C013 C003 C007 120.0(6) . . ?
C003 C007 H007 120.0 . . ?
C00M C007 C003 120.0(6) . . ?
C00M C007 H007 120.0 . . ?
C00J C009 C00N 124.8(5) . . ?
C00M C009 C00J 119.1(5) . . ?
C00M C009 C00N 116.0(5) . . ?
O001 C00G O005 123.8(4) . . ?
O001 C00G C00N 123.8(5) . . ?
O005 C00G C00N 112.2(4) . . ?
C009 C00J H00J 120.1 . . ?
C009 C00J C013 119.8(5) . . ?
C013 C00J H00J 120.1 . . ?
O005 C00K H00A 109.5 . . ?
O005 C00K H00B 109.5 . . ?
O005 C00K H00C 109.5 . . ?
H00A C00K H00B 109.5 . . ?
H00A C00K H00C 109.5 . . ?
H00B C00K H00C 109.5 . . ?
C007 C00M H00M 119.2 . . ?
C009 C00M C007 121.6(6) . . ?
C009 C00M H00M 119.2 . . ?
C009 C00N H00N 109.1 . . ?
C00G C00N C009 108.7(5) . . ?
C00G C00N H00N 109.1 . . ?
C00N C00N C009 106.2(6) 3_465 . ?
C00N C00N C00G 114.4(6) 3_465 . ?
C00N C00N H00N 109.1 3_465 . ?
C003 C013 C00J 119.5(6) . . ?
C003 C013 H013 120.2 . . ?
C00J C013 H013 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C00G C00N C009 77.1(7) . . . . ?
O001 C00G C00N C00N -41.5(10) . . . 3_465 ?
O005 C00G C00N C009 -97.7(5) . . . . ?
O005 C00G C00N C00N 143.7(7) . . . 3_465 ?
C003 C007 C00M C009 -0.8(9) . . . . ?
C007 C003 C013 C00J 0.7(9) . . . . ?
C009 C00J C013 C003 -0.3(9) . . . . ?
C00J C009 C00M C007 1.2(9) . . . . ?
C00J C009 C00N C00G -72.4(7) . . . . ?
C00J C009 C00N C00N 51.1(8) . . . 3_465 ?
C00K O005 C00G O001 -0.5(8) . . . . ?
C00K O005 C00G C00N 174.3(5) . . . . ?
C00M C009 C00J C013 -0.6(9) . . . . ?
C00M C009 C00N C00G 103.4(6) . . . . ?
C00M C009 C00N C00N -133.1(6) . . . 3_465 ?
C00N C009 C00J C013 175.1(5) . . . . ?
C00N C009 C00M C007 -174.8(5) . . . . ?
C013 C003 C007 C00M -0.1(9) . . . . ?
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2245962'
loop_
_audit_author_name
_audit_author_address
'Li Tao'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 O4'
_chemical_formula_weight         260.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.8280(12)
_cell_length_b                   7.9485(9)
_cell_length_c                   15.2171(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.439(6)
_cell_angle_gamma                90.00
_cell_volume                     1303.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4743
_cell_measurement_theta_min      74.52
_cell_measurement_theta_max      6.29

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10313
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.29
_diffrn_reflns_theta_max         74.65
_reflns_number_total             2632
_reflns_number_gt                2194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0883P)²+0.1245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2632
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O001 O 0.69729(8) 0.64940(13) 0.61697(8) 0.0492(3) Uani 1 1 d . . .
O002 O 0.11066(10) 0.97830(13) 0.57229(8) 0.0537(3) Uani 1 1 d . . .
O003 O -0.00139(9) 0.69184(13) 0.44938(9) 0.0548(3) Uani 1 1 d . . .
H003 H -0.0247 0.7900 0.4491 0.082 Uiso 1 1 calc R . .
O004 O 0.09687(11) 0.82015(15) 0.69213(7) 0.0564(3) Uani 1 1 d . . .
C005 C 0.37113(11) 0.52296(16) 0.61400(8) 0.0349(3) Uani 1 1 d . . .
C006 C 0.50368(11) 0.51864(16) 0.62433(8) 0.0351(3) Uani 1 1 d . . .
C007 C 0.12296(11) 0.84444(17) 0.60907(9) 0.0386(3) Uani 1 1 d . . .
C008 C 0.16855(11) 0.68695(16) 0.56773(10) 0.0391(3) Uani 1 1 d . . .
H008 H 0.1317 0.5893 0.5947 0.047 Uiso 1 1 calc R . .
C009 C 0.30965(11) 0.67463(16) 0.58413(9) 0.0371(3) Uani 1 1 d . . .
C00A C 0.57095(11) 0.66559(17) 0.60412(9) 0.0382(3) Uani 1 1 d . . .
C00B C 0.30761(12) 0.37463(18) 0.63577(10) 0.0430(3) Uani 1 1 d . . .
H00B H 0.2214 0.3730 0.6291 0.052 Uiso 1 1 calc R . .
C00C C 0.56553(12) 0.37123(18) 0.65641(9) 0.0426(3) Uani 1 1 d . . .
H00C H 0.6518 0.3690 0.6634 0.051 Uiso 1 1 calc R . .
C00D C 0.38022(12) 0.81072(17) 0.56627(11) 0.0440(4) Uani 1 1 d . . .
H00D H 0.3402 0.9094 0.5469 0.053 Uiso 1 1 calc R . .
C00E C 0.12923(13) 0.68582(19) 0.46887(10) 0.0481(4) Uani 1 1 d . . .
H00A H 0.1660 0.7818 0.4418 0.058 Uiso 1 1 calc R . .
H00E H 0.1608 0.5847 0.4432 0.058 Uiso 1 1 calc R . .
C00F C 0.51082(12) 0.80827(17) 0.57584(11) 0.0444(3) Uani 1 1 d . . .
H00F H 0.5555 0.9036 0.5629 0.053 Uiso 1 1 calc R . .
C00G C 0.37077(15) 0.23412(19) 0.66637(11) 0.0501(4) Uani 1 1 d . . .
H00G H 0.3269 0.1386 0.6802 0.060 Uiso 1 1 calc R . .
C00H C 0.50052(15) 0.23237(19) 0.67717(10) 0.0491(4) Uani 1 1 d . . .
H00H H 0.5424 0.1364 0.6985 0.059 Uiso 1 1 calc R . .
C00I C 0.05456(19) 0.9668(3) 0.73733(13) 0.0693(5) Uani 1 1 d . . .
H00I H -0.0154 1.0154 0.7029 0.104 Uiso 1 1 calc R . .
H00J H 0.1203 1.0480 0.7449 0.104 Uiso 1 1 calc R . .
H00K H 0.0307 0.9342 0.7941 0.104 Uiso 1 1 calc R . .
C00J C 0.76871(14) 0.7928(2) 0.60020(15) 0.0643(5) Uani 1 1 d . . .
H00L H 0.7492 0.8282 0.5402 0.096 Uiso 1 1 calc R . .
H00M H 0.8553 0.7655 0.6097 0.096 Uiso 1 1 calc R . .
H00N H 0.7501 0.8821 0.6393 0.096 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
O001 C00A 1.3694(15) . ?
O001 C00J 1.4142(19) . ?
O002 C007 1.2037(17) . ?
O003 C00E 1.4181(16) . ?
O003 H003 0.8200 . ?
O004 C007 1.3351(17) . ?
O004 C00I 1.450(2) . ?
C005 C00B 1.4199(18) . ?
C005 C006 1.4294(16) . ?
C005 C009 1.4303(17) . ?
C006 C00C 1.4134(18) . ?
C006 C00A 1.4255(18) . ?
C007 C008 1.5051(18) . ?
C008 C00E 1.524(2) . ?
C008 C009 1.5278(16) . ?
C008 H008 0.9800 . ?
C009 C00D 1.3664(18) . ?
C00A C00F 1.3573(19) . ?
C00B C00G 1.368(2) . ?
C00B H00B 0.9300 . ?
C00C C00H 1.362(2) . ?
C00C H00C 0.9300 . ?
C00D C00F 1.4080(18) . ?
C00D H00D 0.9300 . ?
C00E H00A 0.9700 . ?
C00E H00E 0.9700 . ?
C00F H00F 0.9300 . ?
C00G C00H 1.399(2) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9600 . ?
C00I H00J 0.9600 . ?
C00I H00K 0.9600 . ?
C00J H00L 0.9600 . ?
C00J H00M 0.9600 . ?
C00J H00N 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
C00A O001 C00J 117.02(11) . . ?
C00E O003 H003 109.5 . . ?
C007 O004 C00I 115.95(13) . . ?
C00B C005 C006 117.25(11) . . ?
C00B C005 C009 123.57(11) . . ?
C006 C005 C009 119.17(11) . . ?
C00C C006 C00A 121.24(11) . . ?
C00C C006 C005 119.73(12) . . ?
C00A C006 C005 119.01(11) . . ?
O002 C007 O004 122.96(13) . . ?
O002 C007 C008 124.55(13) . . ?
O004 C007 C008 112.49(12) . . ?
C007 C008 C00E 110.21(11) . . ?
C007 C008 C009 110.34(10) . . ?
C00E C008 C009 110.02(11) . . ?
C007 C008 H008 108.7 . . ?
C00E C008 H008 108.7 . . ?
C009 C008 H008 108.7 . . ?
C00D C009 C005 118.58(12) . . ?
C00D C009 C008 119.09(11) . . ?
C005 C009 C008 122.28(11) . . ?
C00F C00A O001 124.51(12) . . ?
C00F C00A C006 120.89(12) . . ?
O001 C00A C006 114.59(11) . . ?
C00G C00B C005 121.32(13) . . ?
C00G C00B H00B 119.3 . . ?
C005 C00B H00B 119.3 . . ?
C00H C00C C006 120.89(12) . . ?
C00H C00C H00C 119.6 . . ?
C006 C00C H00C 119.6 . . ?
C009 C00D C00F 122.92(12) . . ?
C009 C00D H00D 118.5 . . ?
C00F C00D H00D 118.5 . . ?
O003 C00E C008 112.70(12) . . ?
O003 C00E H00A 109.1 . . ?
C008 C00E H00A 109.1 . . ?
O003 C00E H00E 109.1 . . ?
C008 C00E H00E 109.1 . . ?
H00A C00E H00E 107.8 . . ?
C00A C00F C00D 119.43(12) . . ?
C00A C00F H00F 120.3 . . ?
C00D C00F H00F 120.3 . . ?
C00B C00G C00H 120.81(13) . . ?
C00B C00G H00G 119.6 . . ?
C00H C00G H00G 119.6 . . ?
C00C C00H C00G 120.00(13) . . ?
C00C C00H H00H 120.0 . . ?
C00G C00H H00H 120.0 . . ?
O004 C00I H00I 109.5 . . ?
O004 C00I H00J 109.5 . . ?
H00I C00I H00J 109.5 . . ?
O004 C00I H00K 109.5 . . ?
H00I C00I H00K 109.5 . . ?
H00J C00I H00K 109.5 . . ?
O001 C00J H00L 109.5 . . ?
O001 C00J H00M 109.5 . . ?
H00L C00J H00M 109.5 . . ?
O001 C00J H00N 109.5 . . ?
H00L C00J H00N 109.5 . . ?
H00M C00J H00N 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        74.65
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2245959'
loop_
_audit_author_name
_audit_author_address
'Li Tao'
;Dalian University of Technology
China
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2024-05-08 downloaded from the CCDC.
;
_audit_creation_date             2023-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 O5'
_chemical_formula_sum            'C17 H18 O5'
_chemical_formula_weight         302.31
_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      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                   5.8137(4)
_cell_length_b                   8.5017(5)
_cell_length_c                   16.6639(10)
_cell_angle_alpha                99.886(3)
_cell_angle_beta                 92.872(3)
_cell_angle_gamma                108.302(3)
_cell_volume                     765.58(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4407
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      74.55
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.799
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6609
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0679 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8768.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7734
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.540
_diffrn_reflns_theta_min         2.708
_diffrn_ambient_temperature      296.5
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.967
_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                2583
_reflns_number_total             3034
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.445
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0523
_refine_ls_restrained_S_all      1.092
_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)+(0.0982P)²+0.1398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1730
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00C)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00K(H00E,H00H,H00K), C00L(H00L,H00M,H00N), C00M(H00O,H00P,H00Q)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.0864(2) 0.66659(15) 0.93196(9) 0.0592(4) Uani 1 1 d . . . . .
O002 O 0.6209(2) 0.20193(16) 0.81986(9) 0.0598(4) Uani 1 1 d . . . . .
O003 O 0.2206(2) 0.11889(17) 0.82346(11) 0.0747(5) Uani 1 1 d . . . . .
O004 O 0.4865(2) 0.73406(18) 0.95888(12) 0.0811(5) Uani 1 1 d . . . . .
O005 O 0.6595(3) 0.85708(18) 0.46744(8) 0.0692(4) Uani 1 1 d . . . . .
C006 C 0.4116(3) 0.22898(19) 0.83095(10) 0.0452(4) Uani 1 1 d . . . . .
C007 C 0.6489(3) 0.66059(18) 0.68031(9) 0.0428(4) Uani 1 1 d . . . . .
C008 C 0.6486(3) 0.59575(19) 0.75300(10) 0.0452(4) Uani 1 1 d . . . . .
H008 H 0.792117 0.629163 0.788133 0.054 Uiso 1 1 calc R . . . .
C009 C 0.4429(3) 0.48540(19) 0.77286(9) 0.0445(4) Uani 1 1 d . . . . .
C00A C 0.4309(3) 0.61122(19) 0.62654(10) 0.0447(4) Uani 1 1 d . . . . .
C00B C 0.4461(3) 0.4171(2) 0.85187(10) 0.0450(4) Uani 1 1 d . . . . .
H00B H 0.605548 0.475582 0.883834 0.054 Uiso 1 1 calc R . . . .
C00C C 0.2927(3) 0.6307(2) 0.93353(10) 0.0468(4) Uani 1 1 d . . . . .
C00D C 0.4298(3) 0.6767(2) 0.55356(10) 0.0513(4) Uani 1 1 d . . . . .
H00D H 0.286603 0.644971 0.518387 0.062 Uiso 1 1 calc R . . . .
C00E C 0.2491(3) 0.4460(2) 0.90416(11) 0.0505(4) Uani 1 1 d . . . . .
H00A H 0.090870 0.394644 0.872101 0.061 Uiso 1 1 calc R . . . .
H00C H 0.247813 0.392056 0.950987 0.061 Uiso 1 1 calc R . . . .
C00F C 0.8613(3) 0.7743(2) 0.65848(11) 0.0547(4) Uani 1 1 d . . . . .
H00F H 1.006669 0.807680 0.692694 0.066 Uiso 1 1 calc R . . . .
C00G C 0.2255(3) 0.4358(2) 0.71848(12) 0.0577(5) Uani 1 1 d . . . . .
H00G H 0.084128 0.360055 0.731024 0.069 Uiso 1 1 calc R . . . .
C00H C 0.6376(4) 0.7855(2) 0.53529(10) 0.0525(4) Uani 1 1 d . . . . .
C00I C 0.8565(3) 0.8353(2) 0.58859(12) 0.0593(5) Uani 1 1 d . . . . .
H00I H 0.997830 0.910369 0.575568 0.071 Uiso 1 1 calc R . . . .
C00J C 0.2202(3) 0.4969(2) 0.64825(11) 0.0584(5) Uani 1 1 d . . . . .
H00J H 0.074879 0.462688 0.613948 0.070 Uiso 1 1 calc R . . . .
C00K C 0.6085(4) 0.0270(2) 0.79681(14) 0.0668(5) Uani 1 1 d . . . . .
H00E H 0.504104 -0.024329 0.746380 0.100 Uiso 1 1 calc GR . . . .
H00H H 0.544303 -0.032441 0.839109 0.100 Uiso 1 1 calc GR . . . .
H00K H 0.768972 0.021753 0.789659 0.100 Uiso 1 1 calc GR . . . .
C00L C 0.1058(4) 0.8396(2) 0.96330(15) 0.0688(5) Uani 1 1 d . . . . .
H00L H 0.228366 0.913102 0.937723 0.103 Uiso 1 1 calc GR . . . .
H00M H 0.150161 0.865996 1.021507 0.103 Uiso 1 1 calc GR . . . .
H00N H -0.048085 0.855120 0.951542 0.103 Uiso 1 1 calc GR . . . .
C00M C 0.4487(5) 0.8095(3) 0.40976(12) 0.0748(6) Uani 1 1 d . . . . .
H00O H 0.486295 0.869353 0.365634 0.112 Uiso 1 1 calc GR . . . .
H00P H 0.319648 0.837116 0.436272 0.112 Uiso 1 1 calc GR . . . .
H00Q H 0.398168 0.690118 0.388471 0.112 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
O001 C00C 1.327(2) . ?
O001 C00L 1.441(2) . ?
O002 C006 1.323(2) . ?
O002 C00K 1.449(2) . ?
O003 C006 1.191(2) . ?
O004 C00C 1.193(2) . ?
O005 C00H 1.367(2) . ?
O005 C00M 1.423(3) . ?
C006 C00B 1.523(2) . ?
C007 C008 1.414(2) . ?
C007 C00A 1.417(2) . ?
C007 C00F 1.417(2) . ?
C008 H008 0.9300 . ?
C008 C009 1.364(2) . ?
C009 C00B 1.529(2) . ?
C009 C00G 1.420(2) . ?
C00A C00D 1.422(2) . ?
C00A C00J 1.412(2) . ?
C00B H00B 0.9800 . ?
C00B C00E 1.528(2) . ?
C00C C00E 1.498(2) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.356(3) . ?
C00E H00A 0.9700 . ?
C00E H00C 0.9700 . ?
C00F H00F 0.9300 . ?
C00F C00I 1.357(3) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.362(3) . ?
C00H C00I 1.417(3) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K H00E 0.9600 . ?
C00K H00H 0.9600 . ?
C00K H00K 0.9600 . ?
C00L H00L 0.9600 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?
C00M H00O 0.9600 . ?
C00M H00P 0.9600 . ?
C00M H00Q 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
C00C O001 C00L 116.50(14) . . ?
C006 O002 C00K 116.29(14) . . ?
C00H O005 C00M 117.35(16) . . ?
O002 C006 C00B 111.53(13) . . ?
O003 C006 O002 123.63(15) . . ?
O003 C006 C00B 124.82(14) . . ?
C008 C007 C00A 119.66(14) . . ?
C008 C007 C00F 122.34(15) . . ?
C00F C007 C00A 118.00(15) . . ?
C007 C008 H008 119.2 . . ?
C009 C008 C007 121.63(14) . . ?
C009 C008 H008 119.2 . . ?
C008 C009 C00B 120.84(14) . . ?
C008 C009 C00G 118.40(15) . . ?
C00G C009 C00B 120.76(14) . . ?
C007 C00A C00D 119.92(15) . . ?
C00J C00A C007 117.78(15) . . ?
C00J C00A C00D 122.30(15) . . ?
C006 C00B C009 109.55(13) . . ?
C006 C00B H00B 108.5 . . ?
C006 C00B C00E 109.71(13) . . ?
C009 C00B H00B 108.5 . . ?
C00E C00B C009 112.08(13) . . ?
C00E C00B H00B 108.5 . . ?
O001 C00C C00E 111.87(14) . . ?
O004 C00C O001 123.03(16) . . ?
O004 C00C C00E 125.02(15) . . ?
C00A C00D H00D 120.0 . . ?
C00H C00D C00A 119.97(16) . . ?
C00H C00D H00D 120.0 . . ?
C00B C00E H00A 109.4 . . ?
C00B C00E H00C 109.4 . . ?
C00C C00E C00B 111.26(13) . . ?
C00C C00E H00A 109.4 . . ?
C00C C00E H00C 109.4 . . ?
H00A C00E H00C 108.0 . . ?
C007 C00F H00F 119.4 . . ?
C00I C00F C007 121.19(16) . . ?
C00I C00F H00F 119.4 . . ?
C009 C00G H00G 119.4 . . ?
C00J C00G C009 121.25(15) . . ?
C00J C00G H00G 119.4 . . ?
O005 C00H C00I 114.01(16) . . ?
C00D C00H O005 125.46(17) . . ?
C00D C00H C00I 120.53(16) . . ?
C00F C00I C00H 120.39(16) . . ?
C00F C00I H00I 119.8 . . ?
C00H C00I H00I 119.8 . . ?
C00A C00J H00J 119.4 . . ?
C00G C00J C00A 121.28(15) . . ?
C00G C00J H00J 119.4 . . ?
O002 C00K H00E 109.5 . . ?
O002 C00K H00H 109.5 . . ?
O002 C00K H00K 109.5 . . ?
H00E C00K H00H 109.5 . . ?
H00E C00K H00K 109.5 . . ?
H00H C00K H00K 109.5 . . ?
O001 C00L H00L 109.5 . . ?
O001 C00L H00M 109.5 . . ?
O001 C00L H00N 109.5 . . ?
H00L C00L H00M 109.5 . . ?
H00L C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?
O005 C00M H00O 109.5 . . ?
O005 C00M H00P 109.5 . . ?
O005 C00M H00Q 109.5 . . ?
H00O C00M H00P 109.5 . . ?
H00O C00M H00Q 109.5 . . ?
H00P C00M H00Q 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
