# Supplementary Information (SI) for Polymer Chemistry.
# 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_20231211_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2ntfxv
_database_code_depnum_ccdc_archive 'CCDC 2467318'
loop_
_audit_author_name
_audit_author_address
'Yu Kitazawa'
;Shinshu University
Japan
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_audit_creation_date             2023-12-11
_audit_creation_method           
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H10 O4'
_chemical_formula_sum            'C8 H8 O4'
_chemical_formula_weight         168.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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                   11.1668(5)
_cell_length_b                   6.0924(3)
_cell_length_c                   11.7374(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.622(4)
_cell_angle_gamma                90
_cell_volume                     798.21(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5202
_cell_measurement_temperature    97
_cell_measurement_theta_max      30.4040
_cell_measurement_theta_min      2.4740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 -16 0.3748
11 3 -11 0.3968
5 5 11 0.1666
-11 -6 -1 0.3650
11 -1 -12 0.2920
11 -1 11 0.0576
-15 1 3 0.2297
-13 1 -8 0.1789
4 7 -9 0.4514
-2 -8 3 0.4522
-2 8 6 0.2618
-11 6 0 0.2195

_exptl_crystal_size_max          0.913
_exptl_crystal_size_mid          0.665
_exptl_crystal_size_min          0.306
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9122 -1.0678 -15.7289 0.0000 0.1019 0.9948
10.5349 2.9237 -11.2408 -0.0000 -0.5314 0.8471
5.2807 5.4177 11.4152 -0.0000 -0.8349 -0.5505
-11.0790 -6.0578 -1.0477 0.0000 0.9879 -0.1549
10.6585 -0.8101 -12.3968 0.2836 -0.2060 0.9365
11.1455 -0.8964 11.2406 0.7512 -0.5457 -0.3714
-15.3371 1.1950 3.4639 -0.6781 0.4926 -0.5455
-13.4467 1.0701 -7.9809 -0.8014 0.5823 0.1366
3.8316 6.9836 -8.8383 -0.5640 -0.6263 0.5382
-1.6830 -8.3812 3.1167 0.6603 0.7333 -0.1622
-1.9004 7.9359 6.0256 -0.6054 -0.6723 -0.4261
-10.5077 6.3943 0.0743 -0.9552 -0.1004 -0.2784

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5875
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.343
_diffrn_reflns_theta_min         3.473
_diffrn_ambient_temperature      97
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  57.00   0.50    7.48    --   20.00  54.00  90.00   96
  2  ω    -72.00 -47.00   0.50    7.48    --   20.00  54.00-150.00   50
  3  ω     -7.00  70.00   0.50    7.48    --   20.00  54.00-150.00  154
  4  ω    -74.00 110.00   0.50    7.48    --   20.00  54.00 -33.60  368
  5  ω    -74.00  42.00   0.50    7.48    --   20.00  54.00 -90.00  232
  6  ω     60.00 110.00   0.50    7.48    --   20.00  54.00 -90.00  100
  7  ω    -73.00 -11.00   0.50    7.48    --   20.00  54.00   0.00  124
  8  ω    -67.00 -35.00   0.50    7.48    --   20.00  54.00  90.00   64
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0421579000
_diffrn_orient_matrix_UB_12      -0.0803220000
_diffrn_orient_matrix_UB_13      0.0186187000
_diffrn_orient_matrix_UB_21      -0.0418052000
_diffrn_orient_matrix_UB_22      -0.0842378000
_diffrn_orient_matrix_UB_23      -0.0138173000
_diffrn_orient_matrix_UB_31      0.0224966000
_diffrn_orient_matrix_UB_32      -0.0059212000
_diffrn_orient_matrix_UB_33      -0.0558183000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1366
_reflns_number_total             1454
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.079
_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)+(0.0390P)²+0.3016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0763
_refine_ls_wR_factor_ref         0.0775
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
O7 O 0.66848(7) 0.60062(13) 0.60943(7) 0.0155(2) Uani 1 1 d . . . . .
O3 O 0.33054(7) 0.26291(13) 0.60182(6) 0.0148(2) Uani 1 1 d . . . . .
O9 O 0.40194(7) 0.60835(13) 0.61282(7) 0.0186(2) Uani 1 1 d . . . . .
O8 O 0.82271(7) 0.36822(14) 0.58312(7) 0.0209(2) Uani 1 1 d . . . . .
C4 C 0.41639(10) 0.41313(19) 0.62370(9) 0.0139(3) Uani 1 1 d . . . . .
C2 C 0.21670(10) 0.34336(19) 0.55417(10) 0.0153(3) Uani 1 1 d . . . . .
C5 C 0.53168(10) 0.31156(19) 0.66212(9) 0.0149(3) Uani 1 1 d . . . . .
C1 C 0.76068(10) 0.51895(18) 0.55218(9) 0.0143(3) Uani 1 1 d . . . . .
C6 C 0.62593(10) 0.4703(2) 0.70393(10) 0.0172(3) Uani 1 1 d . . . . .
H6A H 0.5928 0.5663 0.7609 0.021 Uiso 1 1 calc R U . . .
H6B H 0.6924 0.3903 0.7391 0.021 Uiso 1 1 calc R U . . .
C10 C 0.15007(11) 0.1351(2) 0.51910(11) 0.0207(3) Uani 1 1 d . . . . .
H10A H 0.1982 0.0513 0.4684 0.031 Uiso 1 1 calc R U . . .
H10B H 0.0757 0.1733 0.4812 0.031 Uiso 1 1 calc R U . . .
H10C H 0.1343 0.0493 0.5856 0.031 Uiso 1 1 calc R U . . .
C11 C 0.14838(11) 0.4718(2) 0.64158(11) 0.0215(3) Uani 1 1 d . . . . .
H11A H 0.1447 0.3883 0.7107 0.032 Uiso 1 1 calc R U . . .
H11B H 0.0686 0.5001 0.6126 0.032 Uiso 1 1 calc R U . . .
H11C H 0.1885 0.6085 0.6568 0.032 Uiso 1 1 calc R U . . .
C12 C 0.55122(11) 0.0978(2) 0.65517(10) 0.0198(3) Uani 1 1 d . . . . .
H12A H 0.4917 0.0057 0.6255 0.024 Uiso 1 1 calc R U . . .
H12B H 0.6244 0.0398 0.6800 0.024 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
O7 C1 1.3411(14) . ?
O7 C6 1.4548(14) . ?
O3 C4 1.3448(14) . ?
O3 C2 1.4591(13) . ?
O9 C4 1.2066(14) . ?
O8 C1 1.2004(14) . ?
C4 C5 1.4869(15) . ?
C2 C1 1.5308(15) 3_666 ?
C2 C10 1.5218(16) . ?
C2 C11 1.5137(16) . ?
C5 C6 1.5014(16) . ?
C5 C12 1.3232(17) . ?
C1 C2 1.5308(15) 3_666 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9300 . ?
C12 H12B 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
C1 O7 C6 116.84(9) . . ?
C4 O3 C2 116.95(9) . . ?
O3 C4 C5 112.41(10) . . ?
O9 C4 O3 123.93(10) . . ?
O9 C4 C5 123.67(10) . . ?
O3 C2 C1 109.55(8) . 3_666 ?
O3 C2 C10 103.74(9) . . ?
O3 C2 C11 111.36(9) . . ?
C10 C2 C1 109.09(9) . 3_666 ?
C11 C2 C1 111.55(10) . 3_666 ?
C11 C2 C10 111.26(10) . . ?
C4 C5 C6 115.09(10) . . ?
C12 C5 C4 122.25(11) . . ?
C12 C5 C6 122.60(11) . . ?
O7 C1 C2 110.61(9) . 3_666 ?
O8 C1 O7 125.23(10) . . ?
O8 C1 C2 123.98(10) . 3_666 ?
O7 C6 C5 110.08(9) . . ?
O7 C6 H6A 109.6 . . ?
O7 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12A 120.0 . . ?
C5 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.697
_oxdiff_exptl_absorpt_empirical_full_min 0.650
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_properties_physical    Heat-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_wit_exp_157_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2ntg10
_database_code_depnum_ccdc_archive 'CCDC 2467322'
loop_
_audit_author_name
_audit_author_address
'Yu Kitazawa'
;Shinshu University
Japan
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_audit_creation_date             2024-06-04
_audit_creation_method           
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H6 O4, C11 H8 O4'
_chemical_formula_sum            'C22 H12 O8'
_chemical_formula_weight         404.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   14.0831(13)
_cell_length_b                   15.5331(14)
_cell_length_c                   17.9383(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3924.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1628
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1810
_cell_measurement_theta_min      2.2660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_Laue_measured_fraction_full 0.877
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15853
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.550
_diffrn_reflns_theta_min         2.258
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00 110.00   0.50   10.00    --   20.00  54.00   0.00  240
  2  ω    -10.00 110.00   0.50   10.00    --   20.00  54.00  90.00  240
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0084814000
_diffrn_orient_matrix_UB_12      0.0429051000
_diffrn_orient_matrix_UB_13      -0.0120014000
_diffrn_orient_matrix_UB_21      0.0324953000
_diffrn_orient_matrix_UB_22      0.0058107000
_diffrn_orient_matrix_UB_23      0.0297455000
_diffrn_orient_matrix_UB_31      0.0374467000
_diffrn_orient_matrix_UB_32      -0.0147722000
_diffrn_orient_matrix_UB_33      -0.0230856000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1639
_reflns_number_total             4955
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.226
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4955
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2346
_refine_ls_R_factor_gt           0.0819
_refine_ls_restrained_S_all      0.927
_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)+(0.1450P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2052
_refine_ls_wR_factor_ref         0.3056
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C5(H5), C18(H18), C21(H21), C20(H20), C19(H19)
2.c X=CH2 refined with riding coordinates:
 C30(H30A,H30B)
;
_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
O8 O 0.5881(2) 0.14265(16) 0.34297(13) 0.0466(8) Uani 1 1 d . . . . .
O12 O 0.6107(2) 0.31376(17) 0.36474(15) 0.0511(8) Uani 1 1 d . . . . .
O23 O 0.5878(2) 0.64956(17) 0.29718(14) 0.0516(8) Uani 1 1 d . . . . .
O27 O 0.6116(2) 0.81984(18) 0.31758(15) 0.0536(8) Uani 1 1 d . . . . .
O28 O 0.4734(2) 0.8894(2) 0.32994(17) 0.0663(10) Uani 1 1 d . . . . .
O14 O 0.6915(2) 0.1216(2) 0.43685(15) 0.0672(10) Uani 1 1 d . . . . .
O13 O 0.4720(2) 0.38162(19) 0.3790(2) 0.0717(10) Uani 1 1 d . . . . .
O29 O 0.6907(2) 0.6208(2) 0.38940(16) 0.0743(10) Uani 1 1 d . . . . .
C9 C 0.6764(3) 0.1289(2) 0.3707(2) 0.0439(11) Uani 1 1 d . . . . .
C1 C 0.5189(3) 0.3170(3) 0.3835(2) 0.0458(10) Uani 1 1 d . . . . .
C10 C 0.7505(3) 0.1231(2) 0.3124(2) 0.0449(11) Uani 1 1 d . . . . .
C16 C 0.5197(3) 0.8238(3) 0.3351(2) 0.0485(11) Uani 1 1 d . . . . .
C17 C 0.4799(3) 0.7422(3) 0.3653(2) 0.0447(10) Uani 1 1 d . . . . .
C7 C 0.5138(3) 0.1521(3) 0.3952(2) 0.0448(10) Uani 1 1 d . . . . .
C2 C 0.4806(3) 0.2338(2) 0.4126(2) 0.0426(10) Uani 1 1 d . . . . .
C24 C 0.6742(3) 0.6308(3) 0.3245(2) 0.0482(12) Uani 1 1 d . . . . .
C25 C 0.7479(3) 0.6219(3) 0.2659(2) 0.0492(11) Uani 1 1 d . . . . .
C11 C 0.6512(3) 0.3944(3) 0.3386(2) 0.0507(11) Uani 1 1 d . . . . .
H11A H 0.6522 0.4362 0.3788 0.061 Uiso 1 1 calc R U . . .
H11B H 0.6133 0.4175 0.2982 0.061 Uiso 1 1 calc R U . . .
C26 C 0.6536(3) 0.8989(3) 0.2908(2) 0.0524(11) Uani 1 1 d . . . . .
H26A H 0.6551 0.9415 0.3303 0.063 Uiso 1 1 calc R U . . .
H26B H 0.6169 0.9218 0.2496 0.063 Uiso 1 1 calc R U . . .
C22 C 0.5151(3) 0.6611(3) 0.3499(2) 0.0488(11) Uani 1 1 d . . . . .
C6 C 0.4712(3) 0.0793(3) 0.4235(2) 0.0589(13) Uani 1 1 d . . . . .
H6 H 0.4932 0.0251 0.4099 0.071 Uiso 1 1 calc R U . . .
C4 C 0.3618(3) 0.1673(3) 0.4907(2) 0.0588(13) Uani 1 1 d . . . . .
H4 H 0.3110 0.1722 0.5235 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4019(3) 0.2398(3) 0.4616(2) 0.0548(12) Uani 1 1 d . . . . .
H3 H 0.3775 0.2936 0.4739 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3954(4) 0.0871(3) 0.4721(3) 0.0688(14) Uani 1 1 d . . . . .
H5 H 0.3673 0.0382 0.4922 0.083 Uiso 1 1 calc R U . . .
C18 C 0.4029(3) 0.7485(3) 0.4132(2) 0.0549(12) Uani 1 1 d . . . . .
H18 H 0.3777 0.8024 0.4239 0.066 Uiso 1 1 calc R U . . .
C21 C 0.4738(3) 0.5885(3) 0.3811(3) 0.0617(13) Uani 1 1 d . . . . .
H21 H 0.4967 0.5340 0.3692 0.074 Uiso 1 1 calc R U . . .
C20 C 0.3991(4) 0.5972(4) 0.4296(3) 0.0708(15) Uani 1 1 d . . . . .
H20 H 0.3730 0.5487 0.4521 0.085 Uiso 1 1 calc R U . . .
C19 C 0.3630(3) 0.6768(4) 0.4451(2) 0.0657(14) Uani 1 1 d . . . . .
H19 H 0.3116 0.6825 0.4772 0.079 Uiso 1 1 calc R U . . .
C15 C 0.7289(4) 0.1323(3) 0.2396(2) 0.0725(16) Uani 1 1 d . . . . .
C30 C 0.7283(4) 0.6318(3) 0.1944(2) 0.0837(18) Uani 1 1 d . . . . .
H30A H 0.6667 0.6449 0.1795 0.100 Uiso 1 1 calc R U . . .
H30B H 0.7760 0.6258 0.1590 0.100 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
O8 C9 1.355(5) . ?
O8 C7 1.413(5) . ?
O12 C1 1.337(4) . ?
O12 C11 1.453(4) . ?
O23 C24 1.344(5) . ?
O23 C22 1.405(5) . ?
O27 C16 1.332(5) . ?
O27 C26 1.445(5) . ?
O28 C16 1.214(5) . ?
O14 C9 1.211(4) . ?
O13 C1 1.204(5) . ?
O29 C24 1.198(4) . ?
C9 C10 1.480(6) . ?
C1 C2 1.496(5) . ?
C10 C11 1.487(6) 2_655 ?
C10 C15 1.350(5) . ?
C16 C17 1.488(6) . ?
C17 C22 1.381(5) . ?
C17 C18 1.388(5) . ?
C7 C2 1.387(5) . ?
C7 C6 1.377(5) . ?
C2 C3 1.416(5) . ?
C24 C25 1.483(6) . ?
C25 C26 1.493(6) 2_665 ?
C25 C30 1.321(6) . ?
C11 C10 1.487(6) 2_655 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C26 C25 1.493(6) 2_665 ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C22 C21 1.387(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.365(6) . ?
C4 C5 1.374(6) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.371(6) . ?
C21 H21 0.9300 . ?
C21 C20 1.371(6) . ?
C20 H20 0.9300 . ?
C20 C19 1.366(6) . ?
C19 H19 0.9300 . ?
C30 H30A 0.9300 . ?
C30 H30B 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
C9 O8 C7 116.9(3) . . ?
C1 O12 C11 115.3(3) . . ?
C24 O23 C22 116.3(3) . . ?
C16 O27 C26 115.9(3) . . ?
O8 C9 C10 113.4(3) . . ?
O14 C9 O8 122.4(4) . . ?
O14 C9 C10 124.2(4) . . ?
O12 C1 C2 113.8(4) . . ?
O13 C1 O12 123.0(4) . . ?
O13 C1 C2 123.1(4) . . ?
C9 C10 C11 116.4(3) . 2_655 ?
C15 C10 C9 121.2(4) . . ?
C15 C10 C11 122.4(4) . 2_655 ?
O27 C16 C17 114.3(4) . . ?
O28 C16 O27 122.8(4) . . ?
O28 C16 C17 122.8(4) . . ?
C22 C17 C16 124.7(4) . . ?
C22 C17 C18 117.9(4) . . ?
C18 C17 C16 117.4(4) . . ?
C2 C7 O8 119.6(3) . . ?
C6 C7 O8 118.8(4) . . ?
C6 C7 C2 121.4(4) . . ?
C7 C2 C1 126.2(4) . . ?
C7 C2 C3 117.6(4) . . ?
C3 C2 C1 116.1(4) . . ?
O23 C24 C25 113.3(3) . . ?
O29 C24 O23 123.9(4) . . ?
O29 C24 C25 122.7(4) . . ?
C24 C25 C26 117.2(4) . 2_665 ?
C30 C25 C24 122.0(4) . . ?
C30 C25 C26 120.7(4) . 2_665 ?
O12 C11 C10 108.1(3) . 2_655 ?
O12 C11 H11A 110.1 . . ?
O12 C11 H11B 110.1 . . ?
C10 C11 H11A 110.1 2_655 . ?
C10 C11 H11B 110.1 2_655 . ?
H11A C11 H11B 108.4 . . ?
O27 C26 C25 107.3(3) . 2_665 ?
O27 C26 H26A 110.3 . . ?
O27 C26 H26B 110.3 . . ?
C25 C26 H26A 110.3 2_665 . ?
C25 C26 H26B 110.3 2_665 . ?
H26A C26 H26B 108.5 . . ?
C17 C22 O23 120.8(4) . . ?
C17 C22 C21 120.7(4) . . ?
C21 C22 O23 118.2(4) . . ?
C7 C6 H6 120.1 . . ?
C7 C6 C5 119.7(5) . . ?
C5 C6 H6 120.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(4) . . ?
C5 C4 H4 119.6 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 H3 119.8 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.9(5) . . ?
C4 C5 H5 120.0 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(4) . . ?
C19 C18 H18 119.3 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.8(5) . . ?
C20 C21 H21 120.1 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.3(5) . . ?
C19 C20 H20 119.9 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C25 C30 H30A 120.0 . . ?
C25 C30 H30B 120.0 . . ?
H30A C30 H30B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 17.029
_oxdiff_exptl_absorpt_empirical_full_min 0.765
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_properties_physical    Heat-sensitive,Photo-sensitive
####################################################################### 
# 
# 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_wit_exp_155_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2ntfyw
_database_code_depnum_ccdc_archive 'CCDC 2467319'
loop_
_audit_author_name
_audit_author_address
'Yu Kitazawa'
;Shinshu University
Japan
;
_audit_update_record             
;
2025-06-25 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_audit_creation_date             2024-06-04
_audit_creation_method           
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 O4'
_chemical_formula_sum            'C9 H13 O4'
_chemical_formula_weight         185.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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      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                   6.3393(11)
_cell_length_b                   8.153(3)
_cell_length_c                   9.439(4)
_cell_angle_alpha                78.55(3)
_cell_angle_beta                 86.14(2)
_cell_angle_gamma                79.30(2)
_cell_volume                     469.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    311
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.2440
_cell_measurement_theta_min      3.0360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             198
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.1685
_diffrn_reflns_Laue_measured_fraction_full 0.694
_diffrn_reflns_Laue_measured_fraction_max 0.590
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1968
_diffrn_reflns_point_group_measured_fraction_full 0.694
_diffrn_reflns_point_group_measured_fraction_max 0.590
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.286
_diffrn_reflns_theta_min         2.203
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.694
_diffrn_measured_fraction_theta_max 0.590
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00 110.00   0.50    2.50    --   20.00  54.00   0.00  240
  2  ω    -10.00 110.00   0.50    2.50    --   20.00  54.00  90.00  240
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1098287000
_diffrn_orient_matrix_UB_12      -0.0074766000
_diffrn_orient_matrix_UB_13      0.0151479000
_diffrn_orient_matrix_UB_21      -0.0058073000
_diffrn_orient_matrix_UB_22      -0.0759029000
_diffrn_orient_matrix_UB_23      0.0508929000
_diffrn_orient_matrix_UB_31      0.0297162000
_diffrn_orient_matrix_UB_32      -0.0481140000
_diffrn_orient_matrix_UB_33      -0.0553655000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                463
_reflns_number_total             1657
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.821
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2254
_refine_ls_R_factor_gt           0.0897
_refine_ls_restrained_S_all      0.821
_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)+(0.1481P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2977
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B)
2.b X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C)
;
_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
O4 O 0.2252(6) 0.2733(6) 0.4870(4) 0.0635(15) Uani 1 1 d . . . . .
O8 O 0.5180(8) 0.1940(7) 0.2357(5) 0.0706(17) Uani 1 1 d . . . . .
O9 O 0.2586(8) 0.2261(7) 0.0788(5) 0.0825(19) Uani 1 1 d . . . . .
O10 O 0.5268(7) 0.1991(7) 0.6118(5) 0.096(2) Uani 1 1 d . . . . .
C2 C 0.2346(10) 0.4272(11) 0.2394(7) 0.055(2) Uani 1 1 d . . . . .
C1 C 0.3265(11) 0.2723(11) 0.1761(7) 0.056(2) Uani 1 1 d . . . . .
C3 C 0.3025(10) 0.4140(9) 0.3921(6) 0.060(2) Uani 1 1 d . . . . .
H3A H 0.4579 0.3968 0.3942 0.072 Uiso 1 1 calc R U . . .
H3B H 0.2449 0.5190 0.4255 0.072 Uiso 1 1 calc R U . . .
C5 C 0.3428(10) 0.1856(10) 0.5972(7) 0.061(2) Uani 1 1 d . . . . .
C7 C 0.3665(13) -0.0473(11) 0.8192(7) 0.074(3) Uani 1 1 d . . . . .
H7A H 0.4666 0.0150 0.8490 0.089 Uiso 1 1 calc R U . . .
H7B H 0.2751 -0.0830 0.9019 0.089 Uiso 1 1 calc R U . . .
C13 C -0.0168(10) 0.4529(10) 0.2368(7) 0.073(2) Uani 1 1 d . . . . .
H13A H -0.0604 0.4682 0.1389 0.110 Uiso 1 1 calc R U . . .
H13B H -0.0786 0.5514 0.2764 0.110 Uiso 1 1 calc R U . . .
H13C H -0.0651 0.3546 0.2935 0.110 Uiso 1 1 calc R U . . .
C6 C 0.2345(11) 0.0614(9) 0.6996(7) 0.062(2) Uani 1 1 d . . . . .
C11 C 0.3120(12) 0.5801(9) 0.1454(7) 0.077(2) Uani 1 1 d . . . . .
H11A H 0.4652 0.5666 0.1503 0.115 Uiso 1 1 calc R U . . .
H11B H 0.2455 0.6815 0.1794 0.115 Uiso 1 1 calc R U . . .
H11C H 0.2741 0.5888 0.0471 0.115 Uiso 1 1 calc R U . . .
C12 C 0.0247(11) 0.0556(10) 0.6892(8) 0.086(3) Uani 1 1 d . . . . .
H12A H -0.0555 0.1305 0.6168 0.104 Uiso 1 1 calc R U . . .
H12B H -0.0396 -0.0231 0.7546 0.104 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
O4 C3 1.449(7) . ?
O4 C5 1.326(7) . ?
O8 C1 1.364(7) . ?
O8 C7 1.451(8) 2_656 ?
O9 C1 1.192(7) . ?
O10 C5 1.212(6) . ?
C2 C1 1.507(10) . ?
C2 C3 1.510(8) . ?
C2 C13 1.570(8) . ?
C2 C11 1.520(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.487(9) . ?
C7 O8 1.451(8) 2_656 ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.488(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C6 C12 1.350(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9300 . ?
C12 H12B 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
C5 O4 C3 119.3(5) . . ?
C1 O8 C7 117.8(6) . 2_656 ?
C1 C2 C3 113.2(6) . . ?
C1 C2 C13 108.1(6) . . ?
C1 C2 C11 108.3(6) . . ?
C3 C2 C13 109.5(6) . . ?
C3 C2 C11 108.2(5) . . ?
C11 C2 C13 109.5(6) . . ?
O8 C1 C2 110.8(6) . . ?
O9 C1 O8 121.5(8) . . ?
O9 C1 C2 127.4(7) . . ?
O4 C3 C2 110.1(5) . . ?
O4 C3 H3A 109.6 . . ?
O4 C3 H3B 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O4 C5 C6 114.7(5) . . ?
O10 C5 O4 123.5(6) . . ?
O10 C5 C6 121.8(6) . . ?
O8 C7 H7A 110.3 2_656 . ?
O8 C7 H7B 110.3 2_656 . ?
O8 C7 C6 107.0(6) 2_656 . ?
H7A C7 H7B 108.6 . . ?
C6 C7 H7A 110.3 . . ?
C6 C7 H7B 110.3 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C6 C7 116.1(6) . . ?
C12 C6 C5 121.5(6) . . ?
C12 C6 C7 122.2(7) . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 120.0 . . ?
C6 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.898
_oxdiff_exptl_absorpt_empirical_full_min 0.465
_exptl_crystal_recrystallization_method 'Vapour deposition'
_chemical_properties_physical    Heat-sensitive,Photo-sensitive
