# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_mo_v468GuillotICMMO
_database_code_depnum_ccdc_archive 'CCDC 2088738'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2021-06-08 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H10 O4'
_chemical_formula_sum            'C7 H10 O4'
_chemical_formula_weight         158.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.2698(10)
_cell_length_b                   7.5782(14)
_cell_length_c                   10.1856(19)
_cell_angle_alpha                100.249(11)
_cell_angle_beta                 91.298(12)
_cell_angle_gamma                98.547(11)
_cell_volume                     395.33(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    1527
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      24.66


_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8803
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16345
_diffrn_reflns_av_unetI/netI     0.2992
_diffrn_reflns_av_R_equivalents  0.3871
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         30.594
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2434
_reflns_number_gt                983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2434
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2441
_refine_ls_R_factor_gt           0.0878
_refine_ls_wR_factor_ref         0.1658
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.956
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_RINTA01_mo_v468GuillotICMMO 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystal was small and very weakly diffracting
 despite 120 s exposure per frame.
;
_vrf_PLAT020_mo_v468GuillotICMMO 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.387 Report
RESPONSE: The crystal was small and very weakly diffracting
 despite 120 s exposure per frame.
;
# end Validation Reply Form

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
C1 C 0.2952(5) 0.6234(4) 0.9301(3) 0.0147(7) Uani 1 1 d . . . . .
C2 C 0.5240(5) 0.7177(4) 0.8747(3) 0.0149(7) Uani 1 1 d . . . . .
C3 C 0.5352(5) 0.6721(4) 0.7251(3) 0.0173(7) Uani 1 1 d . . . . .
H3A H 0.522283 0.538900 0.697270 0.021 Uiso 1 1 calc R U . . .
H3B H 0.703272 0.728575 0.698491 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3233(5) 0.7367(4) 0.6536(3) 0.0160(7) Uani 1 1 d . . . . .
C5 C 0.7022(6) 0.8315(4) 0.9525(3) 0.0242(8) Uani 1 1 d . . . . .
H5A H 0.685942 0.854810 1.046423 0.029 Uiso 1 1 calc R U . . .
H5B H 0.846959 0.890227 0.914583 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1146(6) 0.7118(4) 0.4386(3) 0.0210(7) Uani 1 1 d . . . . .
H6A H -0.036659 0.734362 0.491272 0.025 Uiso 1 1 calc R U . . .
H6B H 0.058562 0.609661 0.363706 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2164(6) 0.8787(4) 0.3838(3) 0.0267(8) Uani 1 1 d . . . . .
H7A H 0.370614 0.858407 0.334960 0.040 Uiso 1 1 calc R U . . .
H7B H 0.259703 0.982113 0.457644 0.040 Uiso 1 1 calc R U . . .
H7C H 0.085185 0.904448 0.323264 0.040 Uiso 1 1 calc R U . . .
O1 O 0.2735(4) 0.6749(3) 1.06021(18) 0.0230(6) Uani 1 1 d . . . . .
H1 H 0.112(6) 0.615(4) 1.0862(10) 0.035 Uiso 1 1 calc R U . . .
O2 O 0.1426(4) 0.5056(3) 0.85999(18) 0.0206(5) Uani 1 1 d . . . . .
O3 O 0.1849(4) 0.8393(3) 0.70494(19) 0.0217(5) Uani 1 1 d . . . . .
O4 O 0.3094(4) 0.6630(3) 0.52290(18) 0.0207(5) Uani 1 1 d . . . . .


_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
C1 O2 1.219(3) . ?
C1 O1 1.325(3) . ?
C1 C2 1.484(4) . ?
C2 C5 1.317(4) . ?
C2 C3 1.506(4) . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.204(3) . ?
C4 O4 1.345(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 O4 1.454(3) . ?
C6 C7 1.504(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1 H1 0.97(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
O2 C1 O1 123.4(2) . . ?
O2 C1 C2 121.6(2) . . ?
O1 C1 C2 115.0(2) . . ?
C5 C2 C1 121.6(3) . . ?
C5 C2 C3 123.5(2) . . ?
C1 C2 C3 114.9(2) . . ?
C2 C3 C4 112.3(2) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O3 C4 O4 124.4(3) . . ?
O3 C4 C3 125.5(3) . . ?
O4 C4 C3 110.1(2) . . ?
C2 C5 H5A 120.0 . . ?
C2 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
O4 C6 C7 111.1(2) . . ?
O4 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
O4 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C4 O4 C6 117.4(2) . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.077

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

data_mo_v471GuillotICMMO
_database_code_depnum_ccdc_archive 'CCDC 2088739'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2021-06-08 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 O4'
_chemical_formula_sum            'C12 H12 O4'
_chemical_formula_weight         220.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   17.407(9)
_cell_length_b                   5.143(2)
_cell_length_c                   25.561(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.287(13)
_cell_angle_gamma                90
_cell_volume                     2146.6(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2557
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.36


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8716
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38761
_diffrn_reflns_av_unetI/netI     0.2241
_diffrn_reflns_av_R_equivalents  0.2440
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.484
_diffrn_reflns_theta_max         30.623
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2959
_reflns_number_gt                1513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+1.5336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2212
_refine_ls_R_factor_gt           0.0772
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32877(12) 1.0257(4) 0.52968(8) 0.0117(5) Uani 1 1 d . . . . .
C2 C 0.38848(12) 1.2351(4) 0.55545(8) 0.0128(5) Uani 1 1 d . . . . .
C3 C 0.37303(13) 1.3795(4) 0.60260(8) 0.0129(5) Uani 1 1 d . . . . .
H3A H 0.408254 1.535994 0.612233 0.015 Uiso 1 1 calc R U . . .
H3B H 0.315225 1.437337 0.590075 0.015 Uiso 1 1 calc R U . . .
C4 C 0.39059(12) 1.2103(4) 0.65383(8) 0.0128(5) Uani 1 1 d . . . . .
C5 C 0.45032(13) 1.2852(4) 0.53748(9) 0.0196(5) Uani 1 1 d . . . . .
H5A H 0.456530 1.186307 0.507813 0.023 Uiso 1 1 calc R U . . .
H5B H 0.488157 1.419915 0.554347 0.023 Uiso 1 1 calc R U . . .
C6 C 0.38473(13) 1.1784(4) 0.74506(8) 0.0142(5) Uani 1 1 d . . . . .
H6A H 0.441219 1.108488 0.758939 0.017 Uiso 1 1 calc R U . . .
H6B H 0.346083 1.030102 0.736461 0.017 Uiso 1 1 calc R U . . .
C7 C 0.37084(12) 1.3480(4) 0.78892(8) 0.0130(5) Uani 1 1 d . . . . .
C8 C 0.42089(13) 1.5625(4) 0.81026(8) 0.0143(5) Uani 1 1 d . . . . .
H8 H 0.462799 1.606536 0.795933 0.017 Uiso 1 1 calc R U . . .
C9 C 0.40983(13) 1.7130(4) 0.85250(9) 0.0187(5) Uani 1 1 d . . . . .
H9 H 0.443657 1.860275 0.866454 0.022 Uiso 1 1 calc R U . . .
C10 C 0.34879(14) 1.6470(4) 0.87443(9) 0.0204(5) Uani 1 1 d . . . . .
H10 H 0.341580 1.748317 0.903459 0.024 Uiso 1 1 calc R U . . .
C11 C 0.29924(13) 1.4339(4) 0.85357(9) 0.0192(5) Uani 1 1 d . . . . .
H11 H 0.257902 1.388378 0.868313 0.023 Uiso 1 1 calc R U . . .
C12 C 0.30986(13) 1.2857(4) 0.81093(9) 0.0170(5) Uani 1 1 d . . . . .
H12 H 0.275251 1.140410 0.796612 0.020 Uiso 1 1 calc R U . . .
O1 O 0.26640(8) 0.9958(3) 0.54158(5) 0.0145(3) Uani 1 1 d . . . . .
O2 O 0.34784(9) 0.8754(3) 0.49357(6) 0.0178(4) Uani 1 1 d . . . . .
H2 H 0.3108(13) 0.752(4) 0.4816(8) 0.027 Uiso 1 1 calc R U . . .
O3 O 0.41883(9) 0.9926(3) 0.65820(6) 0.0167(4) Uani 1 1 d . . . . .
O4 O 0.37209(8) 1.3332(3) 0.69457(5) 0.0146(4) Uani 1 1 d . . . . .


_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
C1 O1 1.234(2) . ?
C1 O2 1.331(2) . ?
C1 C2 1.483(3) . ?
C2 C5 1.334(3) . ?
C2 C3 1.517(3) . ?
C3 C4 1.512(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.213(2) . ?
C4 O4 1.349(2) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 O4 1.467(2) . ?
C6 C7 1.505(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.394(3) . ?
C7 C12 1.400(3) . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
O2 H2 0.88(2) . ?

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
O1 C1 O2 123.41(18) . . ?
O1 C1 C2 121.45(18) . . ?
O2 C1 C2 115.14(18) . . ?
C5 C2 C1 120.83(19) . . ?
C5 C2 C3 124.44(19) . . ?
C1 C2 C3 114.73(17) . . ?
C4 C3 C2 111.59(17) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
O3 C4 O4 124.01(19) . . ?
O3 C4 C3 124.38(19) . . ?
O4 C4 C3 111.60(17) . . ?
C2 C5 H5A 120.0 . . ?
C2 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
O4 C6 C7 109.07(16) . . ?
O4 C6 H6A 109.9 . . ?
C7 C6 H6A 109.9 . . ?
O4 C6 H6B 109.9 . . ?
C7 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C8 C7 C12 118.81(19) . . ?
C8 C7 C6 120.68(18) . . ?
C12 C7 C6 120.44(19) . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C1 O2 H2 109.5 . . ?
C4 O4 C6 114.93(15) . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.070

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

data_mo_v463GuillotICMMO
_database_code_depnum_ccdc_archive 'CCDC 2088740'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2021-06-08 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;




_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H26 O4'
_chemical_formula_sum            'C15 H26 O4'
_chemical_melting_point          ?


_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         270.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   5.3029(14)
_cell_length_b                   5.4415(15)
_cell_length_c                   28.824(8)
_cell_angle_alpha                87.791(9)
_cell_angle_beta                 87.437(9)
_cell_angle_gamma                66.595(8)
_cell_volume                     762.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2901
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      28.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7893
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_process_details   'Bruker APEX3'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24402
_diffrn_reflns_av_unetI/netI     0.3721
_diffrn_reflns_av_R_equivalents  0.3134
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         2.830
_diffrn_reflns_theta_max         30.538
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4654
_reflns_number_gt                1863
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4654
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2800
_refine_ls_R_factor_gt           0.0945
_refine_ls_wR_factor_ref         0.1471
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# start Validation Reply Form
_vrf_RINTA01_mo_v463GuillotICMMO 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The investigated single crystal was a small-sized,brittle
 and poorly diffracting needle. Numerous datasets were collected
 on single crystals, whereof the one of the highest quality is reported herein. 
;
_vrf_PLAT020_mo_v463GuillotICMMO 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.313 Report
RESPONSE: The investigated single crystal was a small-sized,brittle
 and poorly diffracting needle. Numerous datasets were collected
 on single crystals, whereof the one of the highest quality is reported herein. 
;
# end Validation Reply Form

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
C1 C 0.2751(4) 0.5178(5) 0.45563(8) 0.0128(5) Uani 1 1 d . . . . .
C2 C 0.4920(4) 0.5312(4) 0.42229(8) 0.0111(5) Uani 1 1 d . . . . .
C3 C 0.4128(4) 0.7799(4) 0.39265(8) 0.0131(5) Uani 1 1 d . . . . .
H3A H 0.577838 0.780282 0.375219 0.016 Uiso 1 1 calc R U . . .
H3B H 0.343273 0.937804 0.412828 0.016 Uiso 1 1 calc R U . . .
C4 C 0.1955(4) 0.8034(5) 0.35876(8) 0.0127(5) Uani 1 1 d . . . . .
C5 C 0.7415(4) 0.3367(4) 0.42074(8) 0.0172(6) Uani 1 1 d . . . . .
H5A H 0.784377 0.185239 0.441142 0.021 Uiso 1 1 calc R U . . .
H5B H 0.877353 0.348760 0.399217 0.021 Uiso 1 1 calc R U . . .
C6 C -0.1017(4) 1.0822(4) 0.30231(8) 0.0176(6) Uani 1 1 d . . . . .
H6A H -0.266238 1.089877 0.320865 0.021 Uiso 1 1 calc R U . . .
H6B H -0.055918 0.938856 0.279345 0.021 Uiso 1 1 calc R U . . .
C7 C -0.1580(4) 1.3464(5) 0.27786(8) 0.0173(6) Uani 1 1 d . . . . .
H7A H 0.008921 1.336744 0.259844 0.021 Uiso 1 1 calc R U . . .
H7B H -0.200878 1.487266 0.301215 0.021 Uiso 1 1 calc R U . . .
C8 C -0.3966(4) 1.4223(5) 0.24527(8) 0.0193(6) Uani 1 1 d . . . . .
H8A H -0.352856 1.280829 0.222008 0.023 Uiso 1 1 calc R U . . .
H8B H -0.562565 1.430195 0.263389 0.023 Uiso 1 1 calc R U . . .
C9 C -0.4592(4) 1.6887(5) 0.22019(8) 0.0178(6) Uani 1 1 d . . . . .
H9A H -0.288839 1.685293 0.204163 0.021 Uiso 1 1 calc R U . . .
H9B H -0.516314 1.831583 0.243433 0.021 Uiso 1 1 calc R U . . .
C10 C -0.6823(4) 1.7585(5) 0.18483(8) 0.0196(6) Uani 1 1 d . . . . .
H10A H -0.852960 1.762760 0.200888 0.023 Uiso 1 1 calc R U . . .
H10B H -0.625672 1.615037 0.161686 0.023 Uiso 1 1 calc R U . . .
C11 C -0.7446(4) 2.0256(5) 0.15939(8) 0.0200(6) Uani 1 1 d . . . . .
H11A H -0.802158 2.169255 0.182493 0.024 Uiso 1 1 calc R U . . .
H11B H -0.573926 2.021686 0.143399 0.024 Uiso 1 1 calc R U . . .
C12 C -0.9675(4) 2.0941(5) 0.12387(8) 0.0218(6) Uani 1 1 d . . . . .
H12A H -0.908824 1.951617 0.100526 0.026 Uiso 1 1 calc R U . . .
H12B H -1.137449 2.095676 0.139777 0.026 Uiso 1 1 calc R U . . .
C13 C -1.0317(4) 2.3608(5) 0.09906(8) 0.0217(6) Uani 1 1 d . . . . .
H13A H -0.862001 2.358438 0.082930 0.026 Uiso 1 1 calc R U . . .
H13B H -1.088458 2.502895 0.122446 0.026 Uiso 1 1 calc R U . . .
C14 C -1.2560(4) 2.4314(5) 0.06386(9) 0.0277(7) Uani 1 1 d . . . . .
H14A H -1.424705 2.430021 0.079802 0.033 Uiso 1 1 calc R U . . .
H14B H -1.197517 2.291789 0.040006 0.033 Uiso 1 1 calc R U . . .
C15 C -1.3234(4) 2.7030(5) 0.03989(9) 0.0319(7) Uani 1 1 d . . . . .
H15A H -1.386524 2.843235 0.063155 0.048 Uiso 1 1 calc R U . . .
H15B H -1.468546 2.735799 0.017681 0.048 Uiso 1 1 calc R U . . .
H15C H -1.158526 2.704980 0.023396 0.048 Uiso 1 1 calc R U . . .
O1 O 0.0642(2) 0.7128(3) 0.46438(5) 0.0154(4) Uani 1 1 d . . . . .
O2 O 0.3345(2) 0.2782(3) 0.47533(5) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.205011 0.283300 0.493689 0.025 Uiso 1 1 calc R U . . .
O3 O 0.0926(3) 0.6428(3) 0.35559(5) 0.0199(4) Uani 1 1 d . . . . .
O4 O 0.1277(2) 1.0264(3) 0.33244(5) 0.0163(4) Uani 1 1 d . . . . .


_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
C1 O1 1.222(2) . ?
C1 O2 1.325(3) . ?
C1 C2 1.488(3) . ?
C2 C5 1.326(3) . ?
C2 C3 1.493(3) . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.208(2) . ?
C4 O4 1.336(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 O4 1.452(2) . ?
C6 C7 1.501(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.523(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.511(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.518(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 H2 0.8400 . ?

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
O1 C1 O2 123.6(2) . . ?
O1 C1 C2 122.5(2) . . ?
O2 C1 C2 113.94(18) . . ?
C5 C2 C1 121.2(2) . . ?
C5 C2 C3 123.0(2) . . ?
C1 C2 C3 115.73(17) . . ?
C2 C3 C4 112.41(17) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O3 C4 O4 123.6(2) . . ?
O3 C4 C3 124.8(2) . . ?
O4 C4 C3 111.64(18) . . ?
C2 C5 H5A 120.0 . . ?
C2 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
O4 C6 C7 108.03(16) . . ?
O4 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
O4 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 C8 111.89(17) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 113.17(17) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 114.00(17) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 114.08(17) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 113.88(17) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.86(17) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 114.10(18) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 113.64(19) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O2 H2 109.5 . . ?
C4 O4 C6 115.69(16) . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064

