# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_2aprb_0m
_database_code_depnum_ccdc_archive 'CCDC 1847781'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-10-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H17 O6'
_chemical_formula_sum            'C15 H17 O6'
_chemical_formula_weight         293.28
_chemical_absolute_configuration unk
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8896(9)
_cell_length_b                   10.8408(14)
_cell_length_c                   11.3786(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.397(5)
_cell_angle_gamma                90
_cell_volume                     709.56(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3139
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADAB
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             310
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0891
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6708
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         2.625
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2303
_reflns_number_total             3139
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.0(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.034
_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)+(0.0675P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1344
_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:
 C9(H9), C13(H13), C11(H11), C10(H10), C14(H14), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C3(H3)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C5 C -0.9138(8) -0.1510(4) -0.3523(4) 0.0171(10) Uani 1 1 d . . . . .
C6 C -1.0893(8) -0.0873(4) -0.4314(4) 0.0200(11) Uani 1 1 d . . . . .
H6 H -1.074062 -0.002706 -0.440752 0.024 Uiso 1 1 calc R . . . .
C7 C -1.2858(8) -0.1466(4) -0.4965(4) 0.0185(10) Uani 1 1 d . . . . .
H7 H -1.399033 -0.101944 -0.549008 0.022 Uiso 1 1 calc R . . . .
C9 C -0.6995(8) -0.0879(4) -0.2798(4) 0.0189(10) Uani 1 1 d . . . . .
H9 H -0.582954 -0.081934 -0.329380 0.023 Uiso 1 1 calc R . . . .
C13 C -0.7006(7) -0.5100(4) -0.1104(4) 0.0156(10) Uani 1 1 d . . . . .
H13 H -0.724967 -0.513967 -0.027969 0.019 Uiso 1 1 calc R . . . .
C2 C -1.3122(8) -0.2727(4) -0.4829(4) 0.0174(10) Uani 1 1 d . . . . .
O3 O -0.8504(5) -0.4131(3) -0.1721(2) 0.0161(7) Uani 1 1 d . . . . .
C1 C -1.6698(8) -0.2786(5) -0.6265(4) 0.0274(12) Uani 1 1 d . . . . .
H1A H -1.594140 -0.236305 -0.681645 0.041 Uiso 1 1 calc GR . . . .
H1B H -1.752420 -0.220025 -0.588154 0.041 Uiso 1 1 calc GR . . . .
H1C H -1.777091 -0.337968 -0.669632 0.041 Uiso 1 1 calc GR . . . .
O1 O -1.5005(5) -0.3399(3) -0.5379(3) 0.0231(8) Uani 1 1 d . . . . .
C11 C -0.4105(8) -0.3427(4) -0.0907(4) 0.0180(10) Uani 1 1 d . . . . .
H11 H -0.483464 -0.315320 -0.025501 0.022 Uiso 1 1 calc R . . . .
C8 C -0.7445(9) 0.0400(4) -0.2362(4) 0.0249(12) Uani 1 1 d . . . . .
H8A H -0.604330 0.071833 -0.186358 0.037 Uiso 1 1 calc GR . . . .
H8B H -0.863752 0.035839 -0.190564 0.037 Uiso 1 1 calc GR . . . .
H8C H -0.794067 0.093474 -0.304169 0.037 Uiso 1 1 calc GR . . . .
C3 C -1.1377(8) -0.3376(4) -0.4049(4) 0.0183(10) Uani 1 1 d . . . . .
H3 H -1.154055 -0.422130 -0.395409 0.022 Uiso 1 1 calc R . . . .
C10 C -0.5389(7) -0.2791(4) -0.2063(4) 0.0151(10) Uani 1 1 d . . . . .
H10 H -0.434806 -0.271854 -0.262552 0.018 Uiso 1 1 calc R . . . .
C4 C -0.9402(7) -0.2785(4) -0.3411(4) 0.0148(10) Uani 1 1 d . . . . .
C14 C -0.7536(8) -0.3547(4) -0.2645(4) 0.0153(10) Uani 1 1 d . . . . .
H14 H -0.705988 -0.419058 -0.314763 0.018 Uiso 1 1 calc R . . . .
O2 O -0.6046(5) -0.1591(3) -0.1746(3) 0.0176(7) Uani 1 1 d . . . . .
C12 C -0.4421(8) -0.4811(4) -0.1019(4) 0.0155(10) Uani 1 1 d . . . . .
H12 H -0.349875 -0.520657 -0.029792 0.019 Uiso 1 1 calc R . . . .
O6 O -0.9895(5) -0.6749(3) -0.1444(3) 0.0197(8) Uani 1 1 d . . . . .
O5 O -0.3658(5) -0.5252(3) -0.2053(3) 0.0173(7) Uani 1 1 d . . . . .
O4 O -0.1706(5) -0.3068(3) -0.0593(3) 0.0195(8) Uani 1 1 d . . . . .
C15 C -0.7735(8) -0.6338(4) -0.1689(4) 0.0174(10) Uani 1 1 d . . . . .
H15A H -0.788524 -0.626719 -0.255224 0.021 Uiso 1 1 calc R . . . .
H15B H -0.653895 -0.694421 -0.139173 0.021 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
C5 C6 1.398(6) . ?
C5 C9 1.515(6) . ?
C5 C4 1.400(6) . ?
C6 C7 1.390(6) . ?
C7 C2 1.388(6) . ?
C9 C8 1.515(6) . ?
C9 O2 1.433(5) . ?
C13 O3 1.452(5) . ?
C13 C12 1.536(6) . ?
C13 C15 1.518(6) . ?
C2 O1 1.361(6) . ?
C2 C3 1.396(6) . ?
O3 C14 1.446(5) . ?
C1 O1 1.422(5) . ?
C11 C10 1.533(6) . ?
C11 C12 1.514(6) . ?
C11 O4 1.435(5) . ?
C3 C4 1.389(6) . ?
C10 C14 1.533(6) . ?
C10 O2 1.426(5) . ?
C4 C14 1.496(6) . ?
C12 O5 1.429(5) . ?
O6 C15 1.431(5) . ?

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
C6 C5 C9 122.8(4) . . ?
C6 C5 C4 117.7(4) . . ?
C4 C5 C9 119.5(4) . . ?
C7 C6 C5 122.0(4) . . ?
C2 C7 C6 119.8(4) . . ?
C5 C9 C8 114.0(4) . . ?
O2 C9 C5 110.0(3) . . ?
O2 C9 C8 106.5(4) . . ?
O3 C13 C12 112.0(4) . . ?
O3 C13 C15 110.0(3) . . ?
C15 C13 C12 113.0(4) . . ?
C7 C2 C3 118.8(4) . . ?
O1 C2 C7 125.1(4) . . ?
O1 C2 C3 116.0(4) . . ?
C14 O3 C13 112.0(3) . . ?
C2 O1 C1 117.0(4) . . ?
C12 C11 C10 110.2(4) . . ?
O4 C11 C10 111.7(4) . . ?
O4 C11 C12 112.7(4) . . ?
C4 C3 C2 121.3(4) . . ?
C11 C10 C14 109.8(3) . . ?
O2 C10 C11 107.7(3) . . ?
O2 C10 C14 110.7(3) . . ?
C5 C4 C14 121.1(4) . . ?
C3 C4 C5 120.3(4) . . ?
C3 C4 C14 118.5(4) . . ?
O3 C14 C10 109.7(3) . . ?
O3 C14 C4 108.1(3) . . ?
C4 C14 C10 113.0(4) . . ?
C10 O2 C9 111.0(3) . . ?
C11 C12 C13 108.0(3) . . ?
O5 C12 C13 111.2(4) . . ?
O5 C12 C11 110.2(4) . . ?
O6 C15 C13 111.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_16mard_0m
_database_code_depnum_ccdc_archive 'CCDC 1847786'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-10-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H20 O6'
_chemical_formula_sum            'C15 H20 O6'
_chemical_formula_weight         296.31
_chemical_absolute_configuration unk
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.072(5)
_cell_length_b                   10.504(5)
_cell_length_c                   14.874(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 92.305(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     791.8(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      3.4
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11837
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         3.358
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2994
_reflns_number_total             3937
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXL (Sheldrick, 2015)'
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+0.0025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1275
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C010(H010), C012(H012), C013(H013), C016(H016), C018(H018), C020(H020)
2.b Secondary CH2 refined with riding coordinates:
 C023(H02G,H02H)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C014(H014), C017(H017)
2.d Tetrahedral OH refined with riding coordinates:
 O002(H002), O003(H003), O006(H006)
2.e Idealised Me refined as rotating group:
 C021(H02A,H02B,H02C), C022(H02D,H02E,H02F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.3362(5) -0.2470(2) -0.73404(16) 0.0161(5) Uani 1 1 d . . . . .
O002 O -0.0701(5) -0.3715(2) -1.01335(17) 0.0200(6) Uani 1 1 d . . . . .
H002 H -0.079509 -0.428375 -1.051086 0.030 Uiso 1 1 calc R . . . .
O003 O 0.1368(4) -0.2521(2) -0.86178(16) 0.0157(5) Uani 1 1 d . . . . .
H003 H 0.141187 -0.193799 -0.825083 0.024 Uiso 1 1 calc R . . . .
O004 O -0.5360(4) -0.4678(2) -0.84575(16) 0.0140(5) Uani 1 1 d . . . . .
O006 O -0.2774(5) -0.6957(2) -0.92181(18) 0.0212(6) Uani 1 1 d . . . . .
H006 H -0.321616 -0.698314 -0.869420 0.032 Uiso 1 1 calc R . . . .
O008 O -0.9703(5) -0.7178(2) -0.59011(18) 0.0242(6) Uani 1 1 d . . . . .
C009 C -0.6569(7) -0.5993(4) -0.6768(2) 0.0161(7) Uani 1 1 d . . . . .
H009 H -0.636107 -0.666340 -0.716733 0.019 Uiso 1 1 calc R . . . .
C010 C -0.3528(6) -0.4729(3) -0.7683(2) 0.0123(7) Uani 1 1 d . . . . .
H010 H -0.238003 -0.547513 -0.772686 0.015 Uiso 1 1 calc R . . . .
C011 C -0.5456(6) -0.3850(3) -0.6280(2) 0.0128(7) Uani 1 1 d . . . . .
C012 C -0.4034(7) -0.2601(3) -0.6418(2) 0.0163(7) Uani 1 1 d . . . . .
H012 H -0.241820 -0.258208 -0.603463 0.020 Uiso 1 1 calc R . . . .
C013 C -0.4152(6) -0.4741(3) -0.9322(2) 0.0140(7) Uani 1 1 d . . . . .
H013 H -0.518357 -0.418085 -0.972813 0.017 Uiso 1 1 calc R . . . .
C014 C -0.7131(7) -0.4006(4) -0.5567(2) 0.0181(8) Uani 1 1 d . . . . .
H014 H -0.731818 -0.334652 -0.515739 0.022 Uiso 1 1 calc R . . . .
C015 C -0.5196(6) -0.4850(3) -0.6877(2) 0.0140(7) Uani 1 1 d . . . . .
C016 C -0.1124(7) -0.3131(3) -0.8611(2) 0.0135(7) Uani 1 1 d . . . . .
H016 H -0.242773 -0.249604 -0.881744 0.016 Uiso 1 1 calc R . . . .
C017 C -0.8519(7) -0.5126(4) -0.5459(3) 0.0201(8) Uani 1 1 d . . . . .
H017 H -0.963778 -0.521358 -0.498254 0.024 Uiso 1 1 calc R . . . .
C018 C -0.1879(7) -0.3521(3) -0.7671(2) 0.0134(7) Uani 1 1 d . . . . .
H018 H -0.028184 -0.364588 -0.728811 0.016 Uiso 1 1 calc R . . . .
C019 C -0.8238(7) -0.6113(4) -0.6060(2) 0.0175(8) Uani 1 1 d . . . . .
C020 C -0.1331(7) -0.4216(3) -0.9276(2) 0.0138(7) Uani 1 1 d . . . . .
H020 H -0.008397 -0.489218 -0.909882 0.017 Uiso 1 1 calc R . . . .
C021 C -0.5683(8) -0.1439(4) -0.6227(3) 0.0230(9) Uani 1 1 d . . . . .
H02A H -0.734098 -0.149469 -0.655914 0.035 Uiso 1 1 calc GR . . . .
H02B H -0.476307 -0.068714 -0.640495 0.035 Uiso 1 1 calc GR . . . .
H02C H -0.599049 -0.139817 -0.559485 0.035 Uiso 1 1 calc GR . . . .
C022 C -0.9576(8) -0.8175(4) -0.6549(3) 0.0261(9) Uani 1 1 d . . . . .
H02D H -0.780542 -0.849658 -0.655619 0.039 Uiso 1 1 calc GR . . . .
H02E H -1.008808 -0.785107 -0.713352 0.039 Uiso 1 1 calc GR . . . .
H02F H -1.075068 -0.884984 -0.639268 0.039 Uiso 1 1 calc GR . . . .
C023 C -0.4399(6) -0.6068(3) -0.9709(2) 0.0161(8) Uani 1 1 d . . . . .
H02G H -0.622460 -0.634074 -0.969646 0.019 Uiso 1 1 calc R . . . .
H02H H -0.389993 -0.605528 -1.033125 0.019 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 C012 1.433(4) . ?
O001 C018 1.434(4) . ?
O002 C020 1.427(4) . ?
O003 C016 1.418(4) . ?
O004 C010 1.451(4) . ?
O004 C013 1.448(4) . ?
O006 C023 1.427(4) . ?
O008 C019 1.369(4) . ?
O008 C022 1.426(5) . ?
C009 C015 1.400(5) . ?
C009 C019 1.384(5) . ?
C010 C015 1.501(5) . ?
C010 C018 1.520(5) . ?
C011 C012 1.515(5) . ?
C011 C014 1.394(5) . ?
C011 C015 1.386(5) . ?
C012 C021 1.513(5) . ?
C013 C020 1.532(5) . ?
C013 C023 1.511(5) . ?
C014 C017 1.384(5) . ?
C016 C018 1.521(5) . ?
C016 C020 1.511(5) . ?
C017 C019 1.380(5) . ?

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
C012 O001 C018 113.7(3) . . ?
C013 O004 C010 115.0(2) . . ?
C019 O008 C022 116.4(3) . . ?
C019 C009 C015 119.2(3) . . ?
O004 C010 C015 105.9(3) . . ?
O004 C010 C018 108.3(3) . . ?
C015 C010 C018 112.9(3) . . ?
C014 C011 C012 120.9(3) . . ?
C015 C011 C012 120.7(3) . . ?
C015 C011 C014 118.4(3) . . ?
O001 C012 C011 110.3(3) . . ?
O001 C012 C021 104.9(3) . . ?
C021 C012 C011 113.8(3) . . ?
O004 C013 C020 111.8(3) . . ?
O004 C013 C023 110.4(3) . . ?
C023 C013 C020 114.3(3) . . ?
C017 C014 C011 121.1(3) . . ?
C009 C015 C010 117.7(3) . . ?
C011 C015 C009 121.0(3) . . ?
C011 C015 C010 121.3(3) . . ?
O003 C016 C018 112.7(3) . . ?
O003 C016 C020 112.0(3) . . ?
C020 C016 C018 112.7(3) . . ?
C019 C017 C014 119.8(3) . . ?
O001 C018 C010 110.6(3) . . ?
O001 C018 C016 105.2(3) . . ?
C010 C018 C016 111.8(3) . . ?
O008 C019 C009 124.0(3) . . ?
O008 C019 C017 115.6(3) . . ?
C017 C019 C009 120.5(3) . . ?
O002 C020 C013 109.6(3) . . ?
O002 C020 C016 107.1(3) . . ?
C016 C020 C013 109.9(3) . . ?
O006 C023 C013 111.8(3) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.328 0.048 0.186 49.2 18.3 ?
2 -0.182 0.548 0.814 49.2 18.3 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9jula_0m
_database_code_depnum_ccdc_archive 'CCDC 1847782'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-10-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H18 O6'
_chemical_formula_sum            'C14 H18 O6'
_chemical_formula_weight         282.28
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.0069(4)
_cell_length_b                   9.5409(7)
_cell_length_c                   26.840(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1282.17(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3232
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.3
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.0785
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19776
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.408
_diffrn_reflns_theta_min         2.265
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2271
_reflns_number_total             3232
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXL (Sheldrick, 2015)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
 Flack x determined using 719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.080
_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)+(0.0788P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1464
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C5(H5A), C3(H3), C2(H2), C6(H6A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C10(H10)
2.d Tetrahedral OH refined with riding coordinates:
 O4(H4), O5(H5)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O6 O -0.2331(5) -0.2978(3) -0.92953(10) 0.0203(6) Uani 1 1 d . . . . .
O4 O 0.2966(5) 0.1371(3) -1.00666(8) 0.0194(6) Uani 1 1 d . . . . .
H4 H 0.449080 0.167433 -1.003736 0.029 Uiso 1 1 calc R . . . .
O3 O 0.2688(5) -0.0752(2) -0.87220(8) 0.0152(6) Uani 1 1 d . . . . .
O5 O 0.3500(5) -0.1434(3) -0.97156(9) 0.0192(6) Uani 1 1 d . . . . .
H5 H 0.395906 -0.124142 -1.000077 0.029 Uiso 1 1 calc R . . . .
O2 O 0.4845(5) 0.2699(3) -0.91662(10) 0.0192(6) Uani 1 1 d . . . . .
O1 O -0.3321(6) 0.1239(3) -0.74228(10) 0.0283(7) Uani 1 1 d . . . . .
C4 C 0.1975(7) 0.0971(3) -0.95902(12) 0.0131(8) Uani 1 1 d . . . . .
H4A H 0.039023 0.152907 -0.950972 0.016 Uiso 1 1 calc R . . . .
C5 C 0.3480(8) 0.0679(4) -0.86938(13) 0.0139(7) Uani 1 1 d . . . . .
H5A H 0.512687 0.071218 -0.849681 0.017 Uiso 1 1 calc R . . . .
C3 C 0.1258(7) -0.0590(4) -0.95788(13) 0.0151(8) Uani 1 1 d . . . . .
H3 H -0.023748 -0.077365 -0.980514 0.018 Uiso 1 1 calc R . . . .
C11 C -0.0075(8) 0.1050(4) -0.80415(13) 0.0167(8) Uani 1 1 d . . . . .
H11 H 0.012786 0.011688 -0.794828 0.020 Uiso 1 1 calc R . . . .
C8 C 0.1167(8) 0.2987(4) -0.85693(14) 0.0188(8) Uani 1 1 d . . . . .
C9 C 0.1451(7) 0.1598(4) -0.84307(12) 0.0154(8) Uani 1 1 d . . . . .
C2 C 0.0486(7) -0.0990(4) -0.90495(13) 0.0143(8) Uani 1 1 d . . . . .
H2 H -0.102100 -0.040633 -0.894326 0.017 Uiso 1 1 calc R . . . .
C6 C 0.4147(7) 0.1259(4) -0.92110(13) 0.0150(8) Uani 1 1 d . . . . .
H6A H 0.574986 0.076576 -0.932568 0.018 Uiso 1 1 calc R . . . .
C13 C -0.1889(8) 0.1895(4) -0.77942(13) 0.0200(9) Uani 1 1 d . . . . .
C12 C -0.2192(8) 0.3287(4) -0.79269(14) 0.0227(9) Uani 1 1 d . . . . .
H12 H -0.340006 0.385583 -0.775860 0.027 Uiso 1 1 calc R . . . .
C7 C 0.2714(8) 0.3596(4) -0.90005(14) 0.0222(9) Uani 1 1 d . . . . .
H7A H 0.149991 0.376124 -0.927603 0.027 Uiso 1 1 calc R . . . .
H7B H 0.345498 0.449305 -0.890138 0.027 Uiso 1 1 calc R . . . .
C1 C -0.0246(8) -0.2515(4) -0.89812(13) 0.0166(8) Uani 1 1 d . . . . .
H1A H 0.132428 -0.308413 -0.904339 0.020 Uiso 1 1 calc R . . . .
H1B H -0.077350 -0.266300 -0.863740 0.020 Uiso 1 1 calc R . . . .
C10 C -0.0678(8) 0.3819(4) -0.83124(14) 0.0241(9) Uani 1 1 d . . . . .
H10 H -0.088741 0.475296 -0.840373 0.029 Uiso 1 1 calc R . . . .
C14 C -0.5105(9) 0.2078(5) -0.71437(16) 0.0344(11) Uani 1 1 d . . . . .
H14A H -0.641450 0.247987 -0.736248 0.052 Uiso 1 1 calc GR . . . .
H14B H -0.413005 0.281381 -0.698111 0.052 Uiso 1 1 calc GR . . . .
H14C H -0.598241 0.150990 -0.689798 0.052 Uiso 1 1 calc GR . . . .
H6 H -0.355(11) -0.243(6) -0.936(2) 0.054(17) Uiso 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
O6 C1 1.413(4) . ?
O4 C4 1.424(4) . ?
O3 C5 1.424(4) . ?
O3 C2 1.428(4) . ?
O5 C3 1.430(4) . ?
O2 C6 1.423(4) . ?
O2 C7 1.438(5) . ?
O1 C13 1.378(4) . ?
O1 C14 1.414(5) . ?
C4 C3 1.532(5) . ?
C4 C6 1.515(5) . ?
C5 C9 1.516(5) . ?
C5 C6 1.531(5) . ?
C3 C2 1.521(5) . ?
C11 C9 1.396(5) . ?
C11 C13 1.384(5) . ?
C8 C9 1.384(5) . ?
C8 C7 1.509(5) . ?
C8 C10 1.400(6) . ?
C2 C1 1.512(5) . ?
C13 C12 1.383(5) . ?
C12 C10 1.380(5) . ?

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 O3 C2 113.6(3) . . ?
C6 O2 C7 114.7(3) . . ?
C13 O1 C14 117.0(3) . . ?
O4 C4 C3 111.1(3) . . ?
O4 C4 C6 107.7(3) . . ?
C6 C4 C3 109.4(3) . . ?
O3 C5 C9 113.1(3) . . ?
O3 C5 C6 111.1(3) . . ?
C9 C5 C6 111.1(3) . . ?
O5 C3 C4 111.0(3) . . ?
O5 C3 C2 107.4(3) . . ?
C2 C3 C4 108.8(3) . . ?
C13 C11 C9 120.0(3) . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 C10 118.6(4) . . ?
C10 C8 C7 119.9(4) . . ?
C11 C9 C5 119.9(3) . . ?
C8 C9 C5 119.8(3) . . ?
C8 C9 C11 120.3(3) . . ?
O3 C2 C3 109.8(3) . . ?
O3 C2 C1 105.4(3) . . ?
C1 C2 C3 114.6(3) . . ?
O2 C6 C4 114.1(3) . . ?
O2 C6 C5 109.0(3) . . ?
C4 C6 C5 112.8(3) . . ?
O1 C13 C11 115.1(3) . . ?
O1 C13 C12 124.4(3) . . ?
C12 C13 C11 120.5(3) . . ?
C10 C12 C13 119.1(4) . . ?
O2 C7 C8 112.9(3) . . ?
O6 C1 C2 114.1(3) . . ?
C12 C10 C8 121.5(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_12julb_0m
_database_code_depnum_ccdc_archive 'CCDC 1847783'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_audit_creation_date             2017-10-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C20 H22 O10)'
_chemical_formula_sum            'C40 H44 O20'
_chemical_formula_weight         844.75
_chemical_absolute_configuration unk
_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      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   10.047(5)
_cell_length_b                   15.961(5)
_cell_length_c                   24.731(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     3966(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4949
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            20164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_min         2.533
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4110
_reflns_number_total             4949
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXL (Sheldrick, 2015)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 1586 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.053
_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)+(0.0462P)²+1.8756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0997
_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:
 C11(H11), C14(H14), C15(H15), C9(H9), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.5098(2) 0.45423(12) 0.61221(8) 0.0247(4) Uani 1 1 d . . . . .
O5 O 0.25757(17) 0.26429(11) 0.65027(7) 0.0177(4) Uani 1 1 d . . . . .
O8 O 0.3383(2) 0.01425(12) 0.62655(8) 0.0281(5) Uani 1 1 d . . . . .
O2 O 0.62285(18) 0.07110(11) 0.65974(7) 0.0178(4) Uani 1 1 d . . . . .
O7 O 0.35638(18) 0.10999(11) 0.69322(7) 0.0184(4) Uani 1 1 d . . . . .
O3 O 0.8366(2) 0.32170(11) 0.47817(8) 0.0231(4) Uani 1 1 d . . . . .
O4 O 0.61373(17) 0.30279(10) 0.66619(7) 0.0160(4) Uani 1 1 d . . . . .
O10 O 0.6663(2) -0.01429(11) 0.59227(8) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.7515(3) 0.27649(16) 0.56530(10) 0.0174(5) Uani 1 1 d . . . . .
H4 H 0.763424 0.329076 0.580756 0.021 Uiso 1 1 calc R . . . .
O6 O 0.1796(2) 0.29563(16) 0.73290(8) 0.0376(6) Uani 1 1 d . . . . .
C11 C 0.4341(3) 0.16545(15) 0.65995(10) 0.0154(5) Uani 1 1 d . . . . .
H11 H 0.421250 0.152275 0.621597 0.018 Uiso 1 1 calc R . . . .
O9 O 0.4438(2) 0.57051(13) 0.65564(9) 0.0335(5) Uani 1 1 d . . . . .
C14 C 0.3893(3) 0.25384(16) 0.67186(10) 0.0162(5) Uani 1 1 d . . . . .
H14 H 0.389292 0.263981 0.710939 0.019 Uiso 1 1 calc R . . . .
C6 C 0.6873(3) 0.13124(16) 0.57340(10) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.7585(3) 0.18486(17) 0.48729(11) 0.0213(6) Uani 1 1 d . . . . .
H3 H 0.772843 0.177319 0.450461 0.026 Uiso 1 1 calc R . . . .
C2 C 0.7826(3) 0.26295(16) 0.51109(10) 0.0189(5) Uani 1 1 d . . . . .
C15 C 0.4836(2) 0.31463(16) 0.64361(11) 0.0156(5) Uani 1 1 d . . . . .
H15 H 0.485429 0.302899 0.604719 0.019 Uiso 1 1 calc R . . . .
C1 C 0.8708(3) 0.39996(17) 0.50234(12) 0.0254(6) Uani 1 1 d . . . . .
H1A H 0.792555 0.425158 0.517544 0.038 Uiso 1 1 calc GR . . . .
H1B H 0.907644 0.436486 0.475369 0.038 Uiso 1 1 calc GR . . . .
H1C H 0.935337 0.390901 0.530379 0.038 Uiso 1 1 calc GR . . . .
C5 C 0.7025(2) 0.21047(15) 0.59594(10) 0.0153(5) Uani 1 1 d . . . . .
C17 C 0.0323(3) 0.3028(2) 0.65700(13) 0.0292(7) Uani 1 1 d . . . . .
H17A H -0.036648 0.313951 0.682868 0.044 Uiso 1 1 calc GR . . . .
H17B H 0.009363 0.254023 0.636254 0.044 Uiso 1 1 calc GR . . . .
H17C H 0.041835 0.349980 0.633261 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.5794(3) 0.15355(15) 0.67593(10) 0.0157(5) Uani 1 1 d . . . . .
H9 H 0.583202 0.155418 0.715509 0.019 Uiso 1 1 calc R . . . .
C18 C 0.4450(3) 0.40465(16) 0.65309(11) 0.0199(6) Uani 1 1 d . . . . .
H18A H 0.349222 0.411064 0.650576 0.024 Uiso 1 1 calc R . . . .
H18B H 0.473260 0.422458 0.688790 0.024 Uiso 1 1 calc R . . . .
C8 C 0.6712(3) 0.22263(15) 0.65498(10) 0.0151(5) Uani 1 1 d . . . . .
H8 H 0.755091 0.218880 0.675044 0.018 Uiso 1 1 calc R . . . .
C16 C 0.1597(3) 0.28784(17) 0.68574(11) 0.0205(6) Uani 1 1 d . . . . .
C20 C 0.5561(3) 0.58349(19) 0.57051(14) 0.0361(8) Uani 1 1 d . . . . .
H20A H 0.487664 0.614435 0.552216 0.054 Uiso 1 1 calc GR . . . .
H20B H 0.594967 0.543781 0.546000 0.054 Uiso 1 1 calc GR . . . .
H20C H 0.623527 0.621410 0.583061 0.054 Uiso 1 1 calc GR . . . .
C12 C 0.3197(3) 0.03432(16) 0.67242(11) 0.0207(6) Uani 1 1 d . . . . .
C10 C 0.6563(3) 0.05735(17) 0.60730(11) 0.0197(6) Uani 1 1 d . . . . .
C19 C 0.4972(3) 0.53809(18) 0.61762(13) 0.0265(6) Uani 1 1 d . . . . .
C7 C 0.7139(3) 0.11962(17) 0.51828(11) 0.0219(6) Uani 1 1 d . . . . .
H7 H 0.701164 0.067225 0.502659 0.026 Uiso 1 1 calc R . . . .
C13 C 0.2552(3) -0.01624(19) 0.71614(12) 0.0325(7) Uani 1 1 d . . . . .
H13A H 0.226244 -0.068949 0.701610 0.049 Uiso 1 1 calc GR . . . .
H13B H 0.179965 0.013743 0.730185 0.049 Uiso 1 1 calc GR . . . .
H13C H 0.318159 -0.025958 0.744669 0.049 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
O1 C18 1.439(3) . ?
O1 C19 1.351(3) . ?
O5 C14 1.437(3) . ?
O5 C16 1.370(3) . ?
O8 C12 1.193(3) . ?
O2 C9 1.443(3) . ?
O2 C10 1.358(3) . ?
O7 C11 1.439(3) . ?
O7 C12 1.364(3) . ?
O3 C2 1.355(3) . ?
O3 C1 1.427(3) . ?
O4 C15 1.434(3) . ?
O4 C8 1.431(3) . ?
O10 C10 1.207(3) . ?
C4 C2 1.393(4) . ?
C4 C5 1.388(4) . ?
O6 C16 1.190(3) . ?
C11 C14 1.510(4) . ?
C11 C9 1.524(4) . ?
O9 C19 1.200(4) . ?
C14 C15 1.525(4) . ?
C6 C5 1.391(3) . ?
C6 C10 1.480(4) . ?
C6 C7 1.401(4) . ?
C3 C2 1.399(4) . ?
C3 C7 1.368(4) . ?
C15 C18 1.507(4) . ?
C5 C8 1.506(3) . ?
C17 C16 1.483(4) . ?
C9 C8 1.528(3) . ?
C20 C19 1.494(4) . ?
C12 C13 1.496(4) . ?

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
C19 O1 C18 115.6(2) . . ?
C16 O5 C14 117.1(2) . . ?
C10 O2 C9 119.2(2) . . ?
C12 O7 C11 118.4(2) . . ?
C2 O3 C1 116.8(2) . . ?
C8 O4 C15 114.22(19) . . ?
C5 C4 C2 119.1(2) . . ?
O7 C11 C14 107.6(2) . . ?
O7 C11 C9 107.13(19) . . ?
C14 C11 C9 110.6(2) . . ?
O5 C14 C11 108.1(2) . . ?
O5 C14 C15 109.1(2) . . ?
C11 C14 C15 108.7(2) . . ?
C5 C6 C10 121.4(2) . . ?
C5 C6 C7 119.3(2) . . ?
C7 C6 C10 119.1(2) . . ?
C7 C3 C2 119.9(2) . . ?
O3 C2 C4 124.1(2) . . ?
O3 C2 C3 115.6(2) . . ?
C4 C2 C3 120.3(2) . . ?
O4 C15 C14 107.7(2) . . ?
O4 C15 C18 107.4(2) . . ?
C18 C15 C14 112.1(2) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 C8 120.4(2) . . ?
C6 C5 C8 118.9(2) . . ?
O2 C9 C11 109.4(2) . . ?
O2 C9 C8 112.4(2) . . ?
C11 C9 C8 113.6(2) . . ?
O1 C18 C15 107.4(2) . . ?
O4 C8 C5 112.8(2) . . ?
O4 C8 C9 109.6(2) . . ?
C5 C8 C9 111.2(2) . . ?
O5 C16 C17 110.9(2) . . ?
O6 C16 O5 122.4(3) . . ?
O6 C16 C17 126.7(3) . . ?
O8 C12 O7 123.6(3) . . ?
O8 C12 C13 127.6(3) . . ?
O7 C12 C13 108.8(2) . . ?
O2 C10 C6 117.7(2) . . ?
O10 C10 O2 117.9(2) . . ?
O10 C10 C6 124.3(2) . . ?
O1 C19 C20 111.5(3) . . ?
O9 C19 O1 123.1(3) . . ?
O9 C19 C20 125.4(3) . . ?
C3 C7 C6 120.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
