# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2015346_0m
_database_code_depnum_ccdc_archive 'CCDC 1522578'
_audit_update_record             
;
2016-12-14 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-11-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 O5, C2 H3 N'
_chemical_formula_sum            'C17 H13 N O5'
_chemical_formula_weight         311.28
_chemical_absolute_configuration .
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   3.7206(2)
_cell_length_b                   18.3471(9)
_cell_length_c                   10.1369(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.126(3)
_cell_angle_gamma                90
_cell_volume                     685.02(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2640
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      24.666
_cell_measurement_theta_min      2.220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8854.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9116
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.686
_diffrn_reflns_theta_max         24.686
_diffrn_reflns_theta_min         2.029
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                1530
_reflns_number_total             2319
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.793
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     178
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0595
_refine_ls_restrained_S_all      1.018
_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)+(0.1016P)²+0.6580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 O4, C9
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C4(H4), C7(H7)
4.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
4.c Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O3(H3), O5(H5A)
;
_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
C11 C 0.6029(12) 0.1973(2) 0.3526(5) 0.0238(11) Uani 1 1 d . U . . .
C13 C 0.5957(12) 0.0603(2) 0.3508(4) 0.0244(11) Uani 1 1 d . U . . .
C12 C 0.3885(12) 0.1984(2) 0.2233(4) 0.0217(11) Uani 1 1 d . U . . .
C10 C 0.2696(9) 0.1295(4) 0.1573(3) 0.0227(8) Uani 1 1 d . U . . .
C9 C 0.7040(9) 0.1326(4) 0.4182(3) 0.0279(8) Uani 1 1 d . U . . .
C14 C 0.3936(12) 0.0596(2) 0.2254(4) 0.0232(11) Uani 1 1 d . U . . .
C5 C 0.2990(14) -0.0030(2) 0.1603(5) 0.0287(12) Uani 1 1 d . U . . .
H5 H 0.1641 -0.0018 0.0734 0.034 Uiso 1 1 calc R . . . .
C2 C 0.6129(14) 0.3304(3) 0.3468(5) 0.0346(13) Uani 1 1 d . U . . .
H2 H 0.6888 0.3755 0.3875 0.041 Uiso 1 1 calc R . . . .
C4 C 0.2968(13) 0.2655(2) 0.1581(5) 0.0253(11) Uani 1 1 d . U . . .
H4 H 0.1577 0.2660 0.0719 0.030 Uiso 1 1 calc R . . . .
C3 C 0.4087(14) 0.3295(3) 0.2192(5) 0.0332(13) Uani 1 1 d . U . . .
C1 C 0.7030(13) 0.2663(3) 0.4126(5) 0.0288(12) Uani 1 1 d . U . . .
C8 C 0.7050(14) -0.0062(3) 0.4119(5) 0.0324(13) Uani 1 1 d . U . . .
C7 C 0.6033(14) -0.0716(3) 0.3473(5) 0.0332(13) Uani 1 1 d . U . . .
H7 H 0.6735 -0.1165 0.3901 0.040 Uiso 1 1 calc R . . . .
C6 C 0.4038(14) -0.0720(3) 0.2232(5) 0.0301(12) Uani 1 1 d . U . . .
O4 O 0.2993(13) 0.39721(19) 0.1495(4) 0.0534(12) Uani 1 1 d . U . . .
H4A H 0.4451 0.4305 0.1776 0.080 Uiso 1 1 calc GR . . . .
O1 O 0.8924(7) 0.1300(3) 0.5336(2) 0.0374(7) Uani 1 1 d . U . . .
O3 O 0.9035(10) 0.2703(2) 0.5334(3) 0.0426(11) Uani 1 1 d . U . . .
H3 H 0.9855 0.2288 0.5561 0.064 Uiso 1 1 calc GR . . . .
O2 O 0.0647(7) 0.1300(3) 0.0502(2) 0.0332(7) Uani 1 1 d . U . . .
C15 C 0.2991(13) -0.1359(2) 0.1500(5) 0.0259(12) Uani 1 1 d . U . . .
H15A H 0.4923 -0.1504 0.0989 0.039 Uiso 1 1 calc GR . . . .
H15B H 0.0755 -0.1266 0.0888 0.039 Uiso 1 1 calc GR . . . .
H15C H 0.2568 -0.1752 0.2115 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.5461(16) 0.5360(3) 0.2133(6) 0.0684(16) Uani 1 1 d . U . . .
C16 C 0.5503(19) 0.5917(4) 0.1959(7) 0.0595(19) Uani 1 1 d . U . . .
O5 O 0.8939(10) -0.01098(19) 0.5360(3) 0.0394(11) Uani 1 1 d . U . . .
H5A H 0.9035 0.0302 0.5724 0.059 Uiso 1 1 calc GR . . . .
C17 C 0.5471(14) 0.6713(3) 0.1992(5) 0.0412(14) Uani 1 1 d . U . . .
H17A H 0.3628 0.6896 0.1283 0.062 Uiso 1 1 calc GR . . . .
H17B H 0.7862 0.6898 0.1857 0.062 Uiso 1 1 calc GR . . . .
H17C H 0.4902 0.6878 0.2858 0.062 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
C11 C12 1.434(6) . ?
C11 C9 1.387(8) . ?
C11 C1 1.430(7) . ?
C13 C9 1.520(8) . ?
C13 C14 1.383(6) . ?
C13 C8 1.402(7) . ?
C12 C10 1.468(7) . ?
C12 C4 1.417(6) . ?
C10 C14 1.499(7) . ?
C10 O2 1.235(4) . ?
C9 O1 1.277(4) . ?
C14 C5 1.345(6) . ?
C5 C6 1.447(6) . ?
C2 C3 1.404(7) . ?
C2 C1 1.370(7) . ?
C4 C3 1.364(7) . ?
C3 O4 1.459(6) . ?
C1 O3 1.342(6) . ?
C8 C7 1.394(7) . ?
C8 O5 1.354(6) . ?
C7 C6 1.367(7) . ?
C6 C15 1.413(7) . ?
N1 C16 1.038(8) . ?
C16 C17 1.461(8) . ?

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 C11 C12 121.9(4) . . ?
C9 C11 C1 121.1(4) . . ?
C1 C11 C12 117.0(4) . . ?
C14 C13 C9 119.8(4) . . ?
C14 C13 C8 118.9(4) . . ?
C8 C13 C9 121.2(4) . . ?
C11 C12 C10 119.8(4) . . ?
C4 C12 C11 120.3(4) . . ?
C4 C12 C10 119.9(4) . . ?
C12 C10 C14 118.3(3) . . ?
O2 C10 C12 120.2(6) . . ?
O2 C10 C14 121.5(5) . . ?
C11 C9 C13 119.6(3) . . ?
O1 C9 C11 123.3(6) . . ?
O1 C9 C13 117.1(6) . . ?
C13 C14 C10 120.4(4) . . ?
C5 C14 C13 122.0(4) . . ?
C5 C14 C10 117.5(4) . . ?
C14 C5 C6 119.7(5) . . ?
C1 C2 C3 120.1(5) . . ?
C3 C4 C12 119.9(4) . . ?
C2 C3 O4 120.9(5) . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 O4 117.8(5) . . ?
C2 C1 C11 121.4(4) . . ?
O3 C1 C11 121.0(4) . . ?
O3 C1 C2 117.6(4) . . ?
C7 C8 C13 119.9(5) . . ?
O5 C8 C13 123.2(5) . . ?
O5 C8 C7 116.8(4) . . ?
C6 C7 C8 120.9(5) . . ?
C7 C6 C5 118.5(5) . . ?
C7 C6 C15 124.2(5) . . ?
C15 C6 C5 117.3(4) . . ?
N1 C16 C17 168.7(9) . . ?

_shelx_SHELXL_version_number     2014/7

_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_mo_2015085_0m
_database_code_depnum_ccdc_archive 'CCDC 1522579'
_audit_update_record             
;
2016-12-14 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-11-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C H Cl3, C15 H10 O5'
_chemical_formula_sum            'C16 H11 Cl3 O5'
_chemical_formula_weight         389.60
_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'
Cl Cl 0.1484 0.1585 '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                   6.9658(4)
_cell_length_b                   8.0624(5)
_cell_length_c                   14.6322(9)
_cell_angle_alpha                75.678(4)
_cell_angle_beta                 81.535(4)
_cell_angle_gamma                88.527(4)
_cell_volume                     787.50(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3042
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0648 before and 0.0517 after correction.
The Ratio of minimum to maximum transmission is 0.8389.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13070
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.639
_diffrn_reflns_theta_min         2.607
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2720
_reflns_number_total             3636
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)²+1.2797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1444
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C4(H4A), C7(H7), C2(H2)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
Cl1 Cl 0.81173(14) 0.02809(12) 0.61030(7) 0.0300(2) Uani 1 1 d . . . . .
Cl2 Cl 0.82472(15) 0.38650(12) 0.60869(7) 0.0324(2) Uani 1 1 d . . . . .
Cl3 Cl 1.18277(13) 0.20229(12) 0.58095(6) 0.0280(2) Uani 1 1 d . . . . .
O3 O 0.6718(3) 0.1071(3) -0.16674(16) 0.0158(5) Uani 1 1 d . . . . .
H3 H 0.750(6) 0.087(5) -0.123(3) 0.024 Uiso 1 1 d R . . . .
O4 O 0.0645(3) 0.3565(3) -0.20285(16) 0.0171(5) Uani 1 1 d . . . . .
H4 H -0.002(6) 0.412(5) -0.174(3) 0.026 Uiso 1 1 d R . . . .
O2 O 0.1907(3) 0.4364(3) 0.11465(16) 0.0170(5) Uani 1 1 d . . . . .
O5 O 0.9621(3) 0.0866(3) 0.14004(16) 0.0161(5) Uani 1 1 d . . . . .
H5 H 0.951(6) 0.076(5) 0.084(3) 0.024 Uiso 1 1 d R . . . .
O1 O 0.8160(3) 0.1036(3) -0.01363(15) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.5200(4) 0.1876(4) -0.1292(2) 0.0125(6) Uani 1 1 d . . . . .
C11 C 0.5105(4) 0.2242(4) -0.0391(2) 0.0124(6) Uani 1 1 d . . . . .
C9 C 0.6685(4) 0.1781(4) 0.0170(2) 0.0118(6) Uani 1 1 d . . . . .
C13 C 0.6539(4) 0.2175(4) 0.1099(2) 0.0122(6) Uani 1 1 d . . . . .
C14 C 0.4900(4) 0.3029(4) 0.1454(2) 0.0132(6) Uani 1 1 d . . . . .
C5 C 0.4781(4) 0.3414(4) 0.2326(2) 0.0147(6) Uani 1 1 d . . . . .
H5A H 0.3660 0.3967 0.2557 0.018 Uiso 1 1 calc R . . . .
C6 C 0.6297(5) 0.2998(4) 0.2881(2) 0.0157(6) Uani 1 1 d . . . . .
C15 C 0.6194(5) 0.3453(5) 0.3820(2) 0.0234(7) Uani 1 1 d . . . . .
H15A H 0.7089 0.2734 0.4202 0.035 Uiso 1 1 calc GR . . . .
H15B H 0.4867 0.3263 0.4162 0.035 Uiso 1 1 calc GR . . . .
H15C H 0.6557 0.4660 0.3711 0.035 Uiso 1 1 calc GR . . . .
C3 C 0.2074(4) 0.3143(4) -0.1475(2) 0.0143(6) Uani 1 1 d . . . . .
C4 C 0.1946(4) 0.3516(4) -0.0586(2) 0.0139(6) Uani 1 1 d . . . . .
H4A H 0.0829 0.4067 -0.0349 0.017 Uiso 1 1 calc R . . . .
C12 C 0.3444(4) 0.3085(4) -0.0053(2) 0.0133(6) Uani 1 1 d . . . . .
C10 C 0.3297(4) 0.3540(4) 0.0882(2) 0.0128(6) Uani 1 1 d . . . . .
C7 C 0.7913(5) 0.2166(4) 0.2535(2) 0.0164(6) Uani 1 1 d . . . . .
H7 H 0.8950 0.1885 0.2899 0.020 Uiso 1 1 calc R . . . .
C8 C 0.8032(4) 0.1736(4) 0.1661(2) 0.0137(6) Uani 1 1 d . . . . .
C2 C 0.3682(4) 0.2327(4) -0.1827(2) 0.0143(6) Uani 1 1 d . . . . .
H2 H 0.3752 0.2075 -0.2432 0.017 Uiso 1 1 calc R . . . .
C16 C 0.9412(5) 0.1884(4) 0.6397(2) 0.0205(7) Uani 1 1 d . . . . .
H16 H 0.9432 0.1572 0.7101 0.025 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
Cl1 C16 1.766(3) . ?
Cl2 C16 1.760(3) . ?
Cl3 C16 1.766(4) . ?
O3 H3 0.89(4) . ?
O3 C1 1.346(3) . ?
O4 H4 0.79(4) . ?
O4 C3 1.359(3) . ?
O2 C10 1.230(4) . ?
O5 H5 0.86(4) . ?
O5 C8 1.353(3) . ?
O1 C9 1.258(3) . ?
C1 C11 1.413(4) . ?
C1 C2 1.395(4) . ?
C11 C9 1.455(4) . ?
C11 C12 1.415(4) . ?
C9 C13 1.459(4) . ?
C13 C14 1.418(4) . ?
C13 C8 1.405(4) . ?
C14 C5 1.376(4) . ?
C14 C10 1.484(4) . ?
C5 H5A 0.9500 . ?
C5 C6 1.410(4) . ?
C6 C15 1.499(4) . ?
C6 C7 1.391(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 C4 1.395(4) . ?
C3 C2 1.383(4) . ?
C4 H4A 0.9500 . ?
C4 C12 1.380(4) . ?
C12 C10 1.491(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(4) . ?
C2 H2 0.9500 . ?
C16 H16 1.0000 . ?

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 O3 H3 104(3) . . ?
C3 O4 H4 100(3) . . ?
C8 O5 H5 105(3) . . ?
O3 C1 C11 122.4(3) . . ?
O3 C1 C2 117.2(3) . . ?
C2 C1 C11 120.5(3) . . ?
C1 C11 C9 120.8(3) . . ?
C1 C11 C12 118.3(3) . . ?
C12 C11 C9 120.9(3) . . ?
O1 C9 C11 120.5(3) . . ?
O1 C9 C13 120.1(3) . . ?
C11 C9 C13 119.4(3) . . ?
C14 C13 C9 121.0(3) . . ?
C8 C13 C9 120.9(3) . . ?
C8 C13 C14 118.1(3) . . ?
C13 C14 C10 120.2(3) . . ?
C5 C14 C13 120.8(3) . . ?
C5 C14 C10 119.1(3) . . ?
C14 C5 H5A 119.5 . . ?
C14 C5 C6 121.0(3) . . ?
C6 C5 H5A 119.5 . . ?
C5 C6 C15 121.1(3) . . ?
C7 C6 C5 118.5(3) . . ?
C7 C6 C15 120.3(3) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C3 C4 121.8(3) . . ?
O4 C3 C2 117.4(3) . . ?
C2 C3 C4 120.8(3) . . ?
C3 C4 H4A 120.1 . . ?
C12 C4 C3 119.9(3) . . ?
C12 C4 H4A 120.1 . . ?
C11 C12 C10 120.4(3) . . ?
C4 C12 C11 120.8(3) . . ?
C4 C12 C10 118.9(3) . . ?
O2 C10 C14 121.7(3) . . ?
O2 C10 C12 120.2(3) . . ?
C14 C10 C12 118.1(3) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
O5 C8 C13 122.5(3) . . ?
O5 C8 C7 116.9(3) . . ?
C7 C8 C13 120.6(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
Cl1 C16 Cl3 110.25(18) . . ?
Cl1 C16 H16 108.7 . . ?
Cl2 C16 Cl1 109.96(18) . . ?
Cl2 C16 Cl3 110.56(19) . . ?
Cl2 C16 H16 108.7 . . ?
Cl3 C16 H16 108.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C11 C9 1.1(4) . . . . ?
O3 C1 C11 C12 -179.6(3) . . . . ?
O3 C1 C2 C3 179.4(3) . . . . ?
O4 C3 C4 C12 -179.1(3) . . . . ?
O4 C3 C2 C1 179.5(3) . . . . ?
O1 C9 C13 C14 179.3(3) . . . . ?
O1 C9 C13 C8 0.1(4) . . . . ?
C1 C11 C9 O1 -0.5(4) . . . . ?
C1 C11 C9 C13 -179.9(3) . . . . ?
C1 C11 C12 C4 0.9(4) . . . . ?
C1 C11 C12 C10 -178.4(3) . . . . ?
C11 C1 C2 C3 0.2(5) . . . . ?
C11 C9 C13 C14 -1.3(4) . . . . ?
C11 C9 C13 C8 179.5(3) . . . . ?
C11 C12 C10 O2 175.5(3) . . . . ?
C11 C12 C10 C14 -2.1(4) . . . . ?
C9 C11 C12 C4 -179.8(3) . . . . ?
C9 C11 C12 C10 0.9(4) . . . . ?
C9 C13 C14 C5 -179.3(3) . . . . ?
C9 C13 C14 C10 0.0(4) . . . . ?
C9 C13 C8 O5 -3.2(4) . . . . ?
C9 C13 C8 C7 177.9(3) . . . . ?
C13 C14 C5 C6 1.2(5) . . . . ?
C13 C14 C10 O2 -176.0(3) . . . . ?
C13 C14 C10 C12 1.7(4) . . . . ?
C14 C13 C8 O5 177.6(3) . . . . ?
C14 C13 C8 C7 -1.3(4) . . . . ?
C14 C5 C6 C15 178.5(3) . . . . ?
C14 C5 C6 C7 -0.9(5) . . . . ?
C5 C14 C10 O2 3.3(5) . . . . ?
C5 C14 C10 C12 -179.0(3) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C6 C7 C8 O5 -177.4(3) . . . . ?
C6 C7 C8 C13 1.6(5) . . . . ?
C15 C6 C7 C8 -179.9(3) . . . . ?
C3 C4 C12 C11 -0.9(4) . . . . ?
C3 C4 C12 C10 178.4(3) . . . . ?
C4 C3 C2 C1 -0.2(5) . . . . ?
C4 C12 C10 O2 -3.7(4) . . . . ?
C4 C12 C10 C14 178.6(3) . . . . ?
C12 C11 C9 O1 -179.8(3) . . . . ?
C12 C11 C9 C13 0.8(4) . . . . ?
C10 C14 C5 C6 -178.1(3) . . . . ?
C8 C13 C14 C5 -0.1(4) . . . . ?
C8 C13 C14 C10 179.2(3) . . . . ?
C2 C1 C11 C9 -179.8(3) . . . . ?
C2 C1 C11 C12 -0.5(4) . . . . ?
C2 C3 C4 C12 0.6(5) . . . . ?

_shelx_SHELXL_version_number     2014/7

_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_mo_2015063_0ma
_database_code_depnum_ccdc_archive 'CCDC 1522577'
_audit_update_record             
;
2016-12-14 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-11-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 O5, C3 H6 O'
_chemical_formula_sum            'C18 H16 O6'
_chemical_formula_weight         328.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.6526(9)
_cell_length_b                   13.0136(6)
_cell_length_c                   7.1164(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.118(3)
_cell_angle_gamma                90
_cell_volume                     1513.25(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2510
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0864 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.8965.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            13671
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.742
_diffrn_reflns_theta_min         2.001
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2194
_reflns_number_total             3538
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.065
_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)+(0.0577P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5A), O4(H4A)
;
_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
C11 C 0.23526(10) 0.18331(13) 0.3147(2) 0.0154(4) Uani 1 1 d . . . . .
C14 C 0.39785(10) 0.15222(13) 0.5416(2) 0.0140(4) Uani 1 1 d . . . . .
C13 C 0.36846(10) 0.25314(13) 0.4971(2) 0.0150(4) Uani 1 1 d . . . . .
C12 C 0.26200(10) 0.08178(13) 0.3605(2) 0.0159(4) Uani 1 1 d . . . . .
C2 C 0.10780(10) 0.11343(14) 0.1336(2) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.0556 0.1235 0.0544 0.024 Uiso 1 1 calc R . . . .
C10 C 0.34406(10) 0.06248(13) 0.4825(2) 0.0151(4) Uani 1 1 d . . . . .
C7 C 0.49923(10) 0.31827(14) 0.6674(2) 0.0177(4) Uani 1 1 d . . . . .
H7 H 0.5336 0.3749 0.7121 0.021 Uiso 1 1 calc R . . . .
C4 C 0.21315(10) -0.00132(14) 0.2958(2) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.2318 -0.0692 0.3282 0.022 Uiso 1 1 calc R . . . .
C5 C 0.47632(10) 0.13629(13) 0.6433(2) 0.0158(4) Uani 1 1 d . . . . .
H5 H 0.4954 0.0682 0.6714 0.019 Uiso 1 1 calc R . . . .
C8 C 0.42046(10) 0.33629(13) 0.5643(2) 0.0163(4) Uani 1 1 d . . . . .
C9 C 0.28711(10) 0.27065(13) 0.3824(2) 0.0153(4) Uani 1 1 d . . . . .
C6 C 0.52822(10) 0.21966(13) 0.7056(2) 0.0164(4) Uani 1 1 d . . . . .
C1 C 0.15605(10) 0.19747(14) 0.2011(2) 0.0174(4) Uani 1 1 d . . . . .
C3 C 0.13552(10) 0.01519(14) 0.1816(2) 0.0191(4) Uani 1 1 d . . . . .
C15 C 0.61431(10) 0.20018(14) 0.8108(3) 0.0201(4) Uani 1 1 d . . . . .
H15A H 0.6483 0.1789 0.7194 0.030 Uiso 1 1 calc GR . . . .
H15B H 0.6140 0.1457 0.9057 0.030 Uiso 1 1 calc GR . . . .
H15C H 0.6367 0.2632 0.8758 0.030 Uiso 1 1 calc GR . . . .
O1 O 0.26248(7) 0.36121(9) 0.34044(17) 0.0203(3) Uani 1 1 d . . . . .
O3 O 0.12488(7) 0.29158(9) 0.15540(18) 0.0231(3) Uani 1 1 d . . . . .
H3 H 0.1591 0.3364 0.2034 0.035 Uiso 1 1 calc GR . . . .
O2 O 0.36494(7) -0.02494(9) 0.53447(17) 0.0207(3) Uani 1 1 d . . . . .
O5 O 0.39672(7) 0.43504(9) 0.53512(18) 0.0225(3) Uani 1 1 d . . . . .
H5A H 0.3477 0.4371 0.4775 0.034 Uiso 1 1 calc GR . . . .
O4 O 0.08537(8) -0.06424(10) 0.11414(18) 0.0269(3) Uani 1 1 d . . . . .
H4A H 0.1070 -0.1198 0.1578 0.040 Uiso 1 1 calc GR . . . .
C17 C 0.14499(11) 0.67125(15) 0.2251(3) 0.0232(4) Uani 1 1 d . . . . .
C18 C 0.06629(12) 0.63210(18) 0.1135(3) 0.0373(6) Uani 1 1 d . . . . .
H18A H 0.0301 0.6901 0.0690 0.056 Uiso 1 1 calc GR . . . .
H18B H 0.0402 0.5874 0.1950 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.0767 0.5930 0.0029 0.056 Uiso 1 1 calc GR . . . .
C16 C 0.21119(12) 0.59651(16) 0.2941(3) 0.0316(5) Uani 1 1 d . . . . .
H16A H 0.2419 0.5832 0.1923 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.1873 0.5322 0.3294 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.2481 0.6248 0.4062 0.047 Uiso 1 1 calc GR . . . .
O6 O 0.15684(9) 0.76241(11) 0.2610(2) 0.0390(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
C11 C12 1.412(2) . ?
C11 C9 1.452(2) . ?
C11 C1 1.420(2) . ?
C14 C13 1.416(2) . ?
C14 C10 1.482(2) . ?
C14 C5 1.382(2) . ?
C13 C8 1.411(2) . ?
C13 C9 1.458(2) . ?
C12 C10 1.492(2) . ?
C12 C4 1.378(2) . ?
C2 C1 1.387(2) . ?
C2 C3 1.380(2) . ?
C10 O2 1.226(2) . ?
C7 C8 1.394(2) . ?
C7 C6 1.380(2) . ?
C4 C3 1.405(2) . ?
C5 C6 1.405(2) . ?
C8 O5 1.349(2) . ?
C9 O1 1.2646(19) . ?
C6 C15 1.505(2) . ?
C1 O3 1.345(2) . ?
C3 O4 1.357(2) . ?
C17 C18 1.485(3) . ?
C17 C16 1.481(3) . ?
C17 O6 1.221(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
C12 C11 C9 120.98(15) . . ?
C12 C11 C1 118.03(16) . . ?
C1 C11 C9 120.99(16) . . ?
C13 C14 C10 120.22(14) . . ?
C5 C14 C13 120.49(15) . . ?
C5 C14 C10 119.28(15) . . ?
C14 C13 C9 120.92(15) . . ?
C8 C13 C14 118.20(15) . . ?
C8 C13 C9 120.88(15) . . ?
C11 C12 C10 120.29(15) . . ?
C4 C12 C11 121.17(15) . . ?
C4 C12 C10 118.54(15) . . ?
C3 C2 C1 120.09(16) . . ?
C14 C10 C12 117.90(15) . . ?
O2 C10 C14 121.65(14) . . ?
O2 C10 C12 120.43(15) . . ?
C6 C7 C8 121.23(16) . . ?
C12 C4 C3 119.44(17) . . ?
C14 C5 C6 120.77(16) . . ?
C7 C8 C13 120.22(16) . . ?
O5 C8 C13 122.41(15) . . ?
O5 C8 C7 117.36(15) . . ?
C11 C9 C13 119.47(15) . . ?
O1 C9 C11 120.40(15) . . ?
O1 C9 C13 120.12(16) . . ?
C7 C6 C5 119.04(15) . . ?
C7 C6 C15 121.23(15) . . ?
C5 C6 C15 119.73(15) . . ?
C2 C1 C11 120.48(16) . . ?
O3 C1 C11 121.91(15) . . ?
O3 C1 C2 117.61(15) . . ?
C2 C3 C4 120.77(16) . . ?
O4 C3 C2 117.69(15) . . ?
O4 C3 C4 121.54(16) . . ?
C16 C17 C18 118.39(18) . . ?
O6 C17 C18 122.35(18) . . ?
O6 C17 C16 119.26(18) . . ?

_shelx_SHELXL_version_number     2014/7

_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_mo_2015416_0m
_database_code_depnum_ccdc_archive 'CCDC 1522580'
_audit_update_record             
;
2016-12-14 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-12-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 O5, C4 H8 O2'
_chemical_formula_sum            'C19 H18 O7'
_chemical_formula_weight         358.33
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0520(7)
_cell_length_b                   13.1936(17)
_cell_length_c                   13.2923(17)
_cell_angle_alpha                112.280(5)
_cell_angle_beta                 97.693(5)
_cell_angle_gamma                92.622(5)
_cell_volume                     807.95(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2842
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0980 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.8587.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10730
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.688
_diffrn_reflns_theta_max         24.688
_diffrn_reflns_theta_min         1.677
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1985
_reflns_number_total             2719
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1253P)²+0.3315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1753
_refine_ls_wR_factor_ref         0.2006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Others
 Fixed Sof: O7B(0.5) H17A(0.5) H17B(0.5) H17C(0.5) H17D(0.5) H16A(0.5)
 H16B(0.5) H16C(0.5) H16D(0.5) C19B(0.5) H19A(0.5) H19B(0.5) C18B(0.5)
 H18A(0.5) H18B(0.5) O7A(0.5) C18A(0.5) H18C(0.5) H18D(0.5) C19A(0.5) H19C(0.5)
 H19D(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C17(H17C,H17D), C16(H16A,H16B), C16(H16C,H16D), C19B(H19A,
 H19B), C18B(H18A,H18B), C18A(H18C,H18D), C19A(H19C,H19D)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5A), C7(H7), C4(H4A)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O4(H4)
;
_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
O3 O 1.0408(4) -0.02438(15) 0.20379(15) 0.0235(5) Uani 1 1 d . . . . .
H3 H 0.9227 -0.0196 0.1554 0.035 Uiso 1 1 calc GR . . . .
O1 O 0.6355(4) 0.05461(14) 0.12843(15) 0.0226(5) Uani 1 1 d . . . . .
O5 O 0.2466(4) 0.13693(16) 0.04836(15) 0.0270(5) Uani 1 1 d . . . . .
H5 H 0.3587 0.0914 0.0466 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.6014(4) 0.34999(15) 0.53849(14) 0.0251(5) Uani 1 1 d . . . . .
O4 O 1.3446(4) 0.12021(16) 0.58369(15) 0.0256(5) Uani 1 1 d . . . . .
H4 H 1.3275 0.1730 0.6419 0.038 Uiso 1 1 calc GR . . . .
C2 C 1.1830(5) 0.0481(2) 0.3940(2) 0.0197(6) Uani 1 1 d . . . . .
H2 H 1.3131 -0.0032 0.3837 0.024 Uiso 1 1 calc R . . . .
C1 C 1.0085(5) 0.0480(2) 0.3037(2) 0.0182(6) Uani 1 1 d . . . . .
C11 C 0.8133(5) 0.12303(19) 0.3177(2) 0.0167(6) Uani 1 1 d . . . . .
C12 C 0.8040(5) 0.1990(2) 0.4260(2) 0.0168(6) Uani 1 1 d . . . . .
C10 C 0.6104(5) 0.2833(2) 0.4456(2) 0.0174(6) Uani 1 1 d . . . . .
C14 C 0.4282(5) 0.2847(2) 0.3485(2) 0.0175(6) Uani 1 1 d . . . . .
C5 C 0.2538(5) 0.3655(2) 0.3645(2) 0.0181(6) Uani 1 1 d . . . . .
H5A H 0.2500 0.4176 0.4368 0.022 Uiso 1 1 calc R . . . .
C6 C 0.0832(5) 0.3708(2) 0.2749(2) 0.0196(6) Uani 1 1 d . . . . .
C15 C -0.1010(6) 0.4599(2) 0.2920(2) 0.0237(6) Uani 1 1 d . . . . .
H15A H -0.2140 0.4584 0.3460 0.036 Uiso 1 1 calc GR . . . .
H15B H -0.2151 0.4476 0.2219 0.036 Uiso 1 1 calc GR . . . .
H15C H 0.0058 0.5316 0.3192 0.036 Uiso 1 1 calc GR . . . .
C9 C 0.6295(5) 0.1234(2) 0.2244(2) 0.0183(6) Uani 1 1 d . . . . .
C13 C 0.4356(5) 0.2059(2) 0.2419(2) 0.0172(6) Uani 1 1 d . . . . .
C7 C 0.0898(5) 0.2934(2) 0.1706(2) 0.0214(6) Uani 1 1 d . . . . .
H7 H -0.0243 0.2970 0.1095 0.026 Uiso 1 1 calc R . . . .
C8 C 0.2597(5) 0.2100(2) 0.1528(2) 0.0191(6) Uani 1 1 d . . . . .
C4 C 0.9769(5) 0.1990(2) 0.5152(2) 0.0188(6) Uani 1 1 d . . . . .
H4A H 0.9674 0.2501 0.5874 0.023 Uiso 1 1 calc R . . . .
C3 C 1.1677(5) 0.1225(2) 0.4984(2) 0.0195(6) Uani 1 1 d . . . . .
O6 O 0.3635(5) 0.28872(18) 0.77688(16) 0.0427(6) Uani 1 1 d . . . . .
O7B O 0.7220(9) 0.4050(4) 0.9829(4) 0.0273(11) Uani 0.5 1 d . . P A 1
C17 C 0.5789(11) 0.3708(4) 0.7946(3) 0.0804(15) Uani 1 1 d . U . . .
H17A H 0.7293 0.3312 0.7631 0.096 Uiso 0.5 1 calc R . P B 1
H17B H 0.5187 0.4125 0.7491 0.096 Uiso 0.5 1 calc R . P B 1
H17C H 0.6206 0.3637 0.7217 0.096 Uiso 0.5 1 calc R . P C 2
H17D H 0.5141 0.4439 0.8284 0.096 Uiso 0.5 1 calc R . P C 2
C16 C 0.3730(12) 0.2574(4) 0.8686(3) 0.0819(15) Uani 1 1 d . U . . .
H16A H 0.4762 0.1927 0.8538 0.098 Uiso 0.5 1 calc R . P D 1
H16B H 0.1873 0.2329 0.8718 0.098 Uiso 0.5 1 calc R . P D 1
H16C H 0.2708 0.3084 0.9211 0.098 Uiso 0.5 1 calc R . P E 2
H16D H 0.2729 0.1833 0.8415 0.098 Uiso 0.5 1 calc R . P E 2
C19B C 0.4859(13) 0.3374(6) 0.9747(5) 0.0334(15) Uani 0.5 1 d . . P A 1
H19A H 0.3465 0.3863 1.0028 0.040 Uiso 0.5 1 calc R . P A 1
H19B H 0.5267 0.2984 1.0246 0.040 Uiso 0.5 1 calc R . P A 1
C18B C 0.6836(13) 0.4460(5) 0.8961(5) 0.0316(14) Uani 0.5 1 d . . P A 1
H18A H 0.5639 0.5054 0.9167 0.038 Uiso 0.5 1 calc R . P A 1
H18B H 0.8594 0.4793 0.8921 0.038 Uiso 0.5 1 calc R . P A 1
O7A O 0.7761(10) 0.3480(5) 0.9489(4) 0.0359(13) Uani 0.5 1 d . . P A 2
C18A C 0.7955(12) 0.3693(6) 0.8539(5) 0.0360(15) Uani 0.5 1 d . . P A 2
H18C H 0.9024 0.4416 0.8772 0.043 Uiso 0.5 1 calc R . P A 2
H18D H 0.8985 0.3130 0.8072 0.043 Uiso 0.5 1 calc R . P A 2
C19A C 0.5835(16) 0.2540(6) 0.9203(7) 0.0459(18) Uani 0.5 1 d . . P A 2
H19C H 0.6629 0.1872 0.8769 0.055 Uiso 0.5 1 calc R . P A 2
H19D H 0.5491 0.2467 0.9890 0.055 Uiso 0.5 1 calc R . P A 2


_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
O3 H3 0.8400 . ?
O3 C1 1.346(3) . ?
O1 C9 1.260(3) . ?
O5 H5 0.8400 . ?
O5 C8 1.348(3) . ?
O2 C10 1.223(3) . ?
O4 H4 0.8400 . ?
O4 C3 1.357(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.390(4) . ?
C2 C3 1.378(4) . ?
C1 C11 1.409(4) . ?
C11 C12 1.417(4) . ?
C11 C9 1.449(4) . ?
C12 C10 1.487(4) . ?
C12 C4 1.376(4) . ?
C10 C14 1.489(4) . ?
C14 C5 1.386(4) . ?
C14 C13 1.411(4) . ?
C5 H5A 0.9500 . ?
C5 C6 1.400(4) . ?
C6 C15 1.501(4) . ?
C6 C7 1.381(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9 C13 1.472(4) . ?
C13 C8 1.401(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.395(4) . ?
C4 H4A 0.9500 . ?
C4 C3 1.404(4) . ?
O6 C17 1.429(5) . ?
O6 C16 1.424(4) . ?
O7B C19B 1.423(7) . ?
O7B C18B 1.443(7) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 H17C 0.9900 . ?
C17 H17D 0.9900 . ?
C17 C18B 1.354(7) . ?
C17 C18A 1.266(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 H16C 0.9900 . ?
C16 H16D 0.9900 . ?
C16 C19B 1.425(7) . ?
C16 C19A 1.199(9) . ?
C19B H19A 0.9900 . ?
C19B H19B 0.9900 . ?
C18B H18A 0.9900 . ?
C18B H18B 0.9900 . ?
O7A C18A 1.408(7) . ?
O7A C19A 1.436(9) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?

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 O3 H3 109.5 . . ?
C8 O5 H5 109.5 . . ?
C3 O4 H4 109.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
O3 C1 C2 116.9(2) . . ?
O3 C1 C11 122.4(2) . . ?
C2 C1 C11 120.6(2) . . ?
C1 C11 C12 117.9(2) . . ?
C1 C11 C9 121.2(2) . . ?
C12 C11 C9 120.9(2) . . ?
C11 C12 C10 120.4(2) . . ?
C4 C12 C11 121.4(2) . . ?
C4 C12 C10 118.2(2) . . ?
O2 C10 C12 121.2(2) . . ?
O2 C10 C14 120.8(2) . . ?
C12 C10 C14 118.0(2) . . ?
C5 C14 C10 118.9(2) . . ?
C5 C14 C13 120.7(2) . . ?
C13 C14 C10 120.5(2) . . ?
C14 C5 H5A 119.7 . . ?
C14 C5 C6 120.5(2) . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C15 120.5(2) . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 C15 120.7(2) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C9 C11 120.7(2) . . ?
O1 C9 C13 119.7(2) . . ?
C11 C9 C13 119.5(2) . . ?
C14 C13 C9 120.6(2) . . ?
C8 C13 C14 118.6(2) . . ?
C8 C13 C9 120.8(2) . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C8 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
O5 C8 C13 123.1(2) . . ?
O5 C8 C7 117.2(2) . . ?
C7 C8 C13 119.7(2) . . ?
C12 C4 H4A 120.4 . . ?
C12 C4 C3 119.3(2) . . ?
C3 C4 H4A 120.4 . . ?
O4 C3 C2 117.9(2) . . ?
O4 C3 C4 121.4(2) . . ?
C2 C3 C4 120.7(2) . . ?
C16 O6 C17 111.1(3) . . ?
C19B O7B C18B 108.7(5) . . ?
O6 C17 H17A 106.7 . . ?
O6 C17 H17B 106.7 . . ?
O6 C17 H17C 108.0 . . ?
O6 C17 H17D 108.0 . . ?
H17A C17 H17B 106.6 . . ?
H17C C17 H17D 107.2 . . ?
C18B C17 O6 122.4(4) . . ?
C18B C17 H17A 106.7 . . ?
C18B C17 H17B 106.7 . . ?
C18A C17 O6 117.4(5) . . ?
C18A C17 H17C 108.0 . . ?
C18A C17 H17D 108.0 . . ?
O6 C16 H16A 107.8 . . ?
O6 C16 H16B 107.8 . . ?
O6 C16 H16C 107.1 . . ?
O6 C16 H16D 107.1 . . ?
O6 C16 C19B 117.9(4) . . ?
H16A C16 H16B 107.2 . . ?
H16C C16 H16D 106.8 . . ?
C19B C16 H16A 107.8 . . ?
C19B C16 H16B 107.8 . . ?
C19A C16 O6 121.0(6) . . ?
C19A C16 H16C 107.1 . . ?
C19A C16 H16D 107.1 . . ?
O7B C19B C16 117.6(5) . . ?
O7B C19B H19A 107.9 . . ?
O7B C19B H19B 107.9 . . ?
C16 C19B H19A 107.9 . . ?
C16 C19B H19B 107.9 . . ?
H19A C19B H19B 107.2 . . ?
O7B C18B H18A 108.3 . . ?
O7B C18B H18B 108.3 . . ?
C17 C18B O7B 115.9(5) . . ?
C17 C18B H18A 108.3 . . ?
C17 C18B H18B 108.3 . . ?
H18A C18B H18B 107.4 . . ?
C18A O7A C19A 109.0(6) . . ?
C17 C18A O7A 117.6(5) . . ?
C17 C18A H18C 107.9 . . ?
C17 C18A H18D 107.9 . . ?
O7A C18A H18C 107.9 . . ?
O7A C18A H18D 107.9 . . ?
H18C C18A H18D 107.2 . . ?
C16 C19A O7A 114.8(6) . . ?
C16 C19A H19C 108.6 . . ?
C16 C19A H19D 108.6 . . ?
O7A C19A H19C 108.6 . . ?
O7A C19A H19D 108.6 . . ?
H19C C19A H19D 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C1 C11 C12 -177.2(2) . . . . ?
O3 C1 C11 C9 2.2(4) . . . . ?
O1 C9 C13 C14 -179.1(2) . . . . ?
O1 C9 C13 C8 -0.9(4) . . . . ?
O2 C10 C14 C5 2.2(4) . . . . ?
O2 C10 C14 C13 -178.6(2) . . . . ?
C2 C1 C11 C12 0.9(4) . . . . ?
C2 C1 C11 C9 -179.7(2) . . . . ?
C1 C2 C3 O4 -179.2(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C11 C12 C10 177.4(2) . . . . ?
C1 C11 C12 C4 -0.9(4) . . . . ?
C1 C11 C9 O1 1.8(4) . . . . ?
C1 C11 C9 C13 -177.6(2) . . . . ?
C11 C12 C10 O2 -179.4(2) . . . . ?
C11 C12 C10 C14 0.2(3) . . . . ?
C11 C12 C4 C3 0.4(4) . . . . ?
C11 C9 C13 C14 0.3(4) . . . . ?
C11 C9 C13 C8 178.5(2) . . . . ?
C12 C11 C9 O1 -178.8(2) . . . . ?
C12 C11 C9 C13 1.8(4) . . . . ?
C12 C10 C14 C5 -177.4(2) . . . . ?
C12 C10 C14 C13 1.8(4) . . . . ?
C12 C4 C3 O4 179.2(2) . . . . ?
C12 C4 C3 C2 0.1(4) . . . . ?
C10 C12 C4 C3 -177.9(2) . . . . ?
C10 C14 C5 C6 178.7(2) . . . . ?
C10 C14 C13 C9 -2.1(4) . . . . ?
C10 C14 C13 C8 179.7(2) . . . . ?
C14 C5 C6 C15 -178.6(2) . . . . ?
C14 C5 C6 C7 0.8(4) . . . . ?
C14 C13 C8 O5 -178.3(2) . . . . ?
C14 C13 C8 C7 2.4(4) . . . . ?
C5 C14 C13 C9 177.2(2) . . . . ?
C5 C14 C13 C8 -1.1(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 O5 178.5(2) . . . . ?
C6 C7 C8 C13 -2.2(4) . . . . ?
C15 C6 C7 C8 179.9(2) . . . . ?
C9 C11 C12 C10 -2.0(4) . . . . ?
C9 C11 C12 C4 179.7(2) . . . . ?
C9 C13 C8 O5 3.5(4) . . . . ?
C9 C13 C8 C7 -175.9(2) . . . . ?
C13 C14 C5 C6 -0.5(4) . . . . ?
C4 C12 C10 O2 -1.0(4) . . . . ?
C4 C12 C10 C14 178.5(2) . . . . ?
C3 C2 C1 O3 177.8(2) . . . . ?
C3 C2 C1 C11 -0.4(4) . . . . ?
O6 C17 C18B O7B 41.8(9) . . . . ?
O6 C17 C18A O7A -40.8(9) . . . . ?
O6 C16 C19B O7B -41.5(9) . . . . ?
O6 C16 C19A O7A 46.1(10) . . . . ?
C17 O6 C16 C19B 29.5(7) . . . . ?
C17 O6 C16 C19A -34.7(8) . . . . ?
C16 O6 C17 C18B -31.3(7) . . . . ?
C16 O6 C17 C18A 30.2(7) . . . . ?
C19B O7B C18B C17 -46.2(8) . . . . ?
C18B O7B C19B C16 46.9(8) . . . . ?
C18A O7A C19A C16 -49.3(9) . . . . ?
C19A O7A C18A C17 47.5(9) . . . . ?

_shelx_SHELXL_version_number     2014/7

_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_mo_2015048_0m
_database_code_depnum_ccdc_archive 'CCDC 1522576'
_audit_update_record             
;
2016-12-14 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-11-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 O5, C2 H6 O'
_chemical_formula_sum            'C17 H16 O6'
_chemical_formula_weight         316.30
_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      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                   4.2914(3)
_cell_length_b                   10.3982(7)
_cell_length_c                   16.1764(10)
_cell_angle_alpha                81.924(4)
_cell_angle_beta                 89.829(4)
_cell_angle_gamma                85.327(4)
_cell_volume                     712.28(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2579
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0918 before and 0.0539 after correction.
The Ratio of minimum to maximum transmission is 0.7795.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7391
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.271
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1851
_reflns_number_total             2473
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0475
_refine_ls_restrained_S_all      1.086
_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)+(0.0891P)²+0.1800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1594
_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 Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C5(H5A), C4(H4A)
2.c Tetrahedral OH refined with riding coordinates:
 O5(H5), O3(H3), O6(H6)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_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
O5 O 0.7658(3) 0.45969(13) 0.12951(9) 0.0250(4) Uani 1 1 d . . . . .
H5 H 0.7052 0.4347 0.1781 0.037 Uiso 1 1 calc R . . . .
O1 O 0.4341(3) 0.46889(13) 0.26150(8) 0.0227(4) Uani 1 1 d . . . . .
O3 O 0.1102(4) 0.47173(13) 0.39375(8) 0.0247(4) Uani 1 1 d . . . . .
H3 H 0.2375 0.4415 0.3604 0.037 Uiso 1 1 calc R . . . .
O4 O -0.5670(4) 0.85065(15) 0.41482(9) 0.0272(4) Uani 1 1 d . . . . .
H4 H -0.610(6) 0.805(2) 0.4659(17) 0.041 Uiso 1 1 d R . . . .
O6 O 0.7240(4) 0.25275(15) 0.43285(9) 0.0323(5) Uani 1 1 d . . . . .
H6 H 0.8164 0.3213 0.4226 0.048 Uiso 1 1 calc R . . . .
C2 C -0.2274(5) 0.6577(2) 0.40534(12) 0.0218(5) Uani 1 1 d . . . . .
H2 H -0.2859 0.6184 0.4591 0.026 Uiso 1 1 calc R . . . .
C1 C -0.0116(5) 0.59183(19) 0.35938(12) 0.0200(5) Uani 1 1 d . . . . .
C11 C 0.0774(5) 0.64773(19) 0.27880(12) 0.0190(5) Uani 1 1 d . . . . .
C9 C 0.3071(5) 0.57937(19) 0.23144(12) 0.0192(5) Uani 1 1 d . . . . .
C13 C 0.3923(5) 0.63985(18) 0.14788(12) 0.0177(5) Uani 1 1 d . . . . .
C8 C 0.6139(5) 0.57601(19) 0.10037(13) 0.0199(5) Uani 1 1 d . . . . .
C7 C 0.6844(5) 0.6334(2) 0.01990(12) 0.0222(5) Uani 1 1 d . . . . .
H7 H 0.8318 0.5887 -0.0121 0.027 Uiso 1 1 calc R . . . .
C6 C 0.5460(5) 0.7528(2) -0.01405(12) 0.0210(5) Uani 1 1 d . . . . .
C15 C 0.6278(5) 0.8117(2) -0.10102(12) 0.0247(5) Uani 1 1 d . . . . .
H15A H 0.7415 0.8890 -0.0983 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.4357 0.8366 -0.1340 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.7595 0.7477 -0.1274 0.037 Uiso 1 1 calc GR . . . .
C14 C 0.2524(5) 0.76327(19) 0.11308(12) 0.0186(5) Uani 1 1 d . . . . .
C5 C 0.3303(5) 0.81883(19) 0.03353(12) 0.0200(5) Uani 1 1 d . . . . .
H5A H 0.2367 0.9023 0.0111 0.024 Uiso 1 1 calc R . . . .
C10 C 0.0204(5) 0.83565(19) 0.16151(12) 0.0196(5) Uani 1 1 d . . . . .
C12 C -0.0614(5) 0.77232(19) 0.24727(12) 0.0181(5) Uani 1 1 d . . . . .
C3 C -0.3588(5) 0.7809(2) 0.37321(12) 0.0220(5) Uani 1 1 d . . . . .
C4 C -0.2736(5) 0.83813(19) 0.29301(12) 0.0202(5) Uani 1 1 d . . . . .
H4A H -0.3632 0.9223 0.2706 0.024 Uiso 1 1 calc R . . . .
O2 O -0.1009(4) 0.94193(14) 0.13332(9) 0.0278(4) Uani 1 1 d . . . . .
C17 C 0.9550(7) 0.1737(2) 0.30907(15) 0.0395(7) Uani 1 1 d . . . . .
H17A H 0.7519 0.1873 0.2803 0.059 Uiso 1 1 calc GR . . . .
H17B H 1.0766 0.0991 0.2907 0.059 Uiso 1 1 calc GR . . . .
H17C H 1.0687 0.2519 0.2958 0.059 Uiso 1 1 calc GR . . . .
C16 C 0.9059(6) 0.1473(2) 0.40139(14) 0.0353(6) Uani 1 1 d . . . . .
H16A H 0.7978 0.0664 0.4146 0.042 Uiso 1 1 calc R . . . .
H16B H 1.1119 0.1330 0.4301 0.042 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
O5 H5 0.8400 . ?
O5 C8 1.350(2) . ?
O1 C9 1.263(2) . ?
O3 H3 0.8400 . ?
O3 C1 1.357(2) . ?
O4 H4 0.92(3) . ?
O4 C3 1.343(3) . ?
O6 H6 0.8400 . ?
O6 C16 1.444(3) . ?
C2 H2 0.9500 . ?
C2 C1 1.384(3) . ?
C2 C3 1.388(3) . ?
C1 C11 1.416(3) . ?
C11 C9 1.449(3) . ?
C11 C12 1.409(3) . ?
C9 C13 1.467(3) . ?
C13 C8 1.404(3) . ?
C13 C14 1.413(3) . ?
C8 C7 1.397(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.373(3) . ?
C6 C15 1.506(3) . ?
C6 C5 1.401(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 C5 1.386(3) . ?
C14 C10 1.487(3) . ?
C5 H5A 0.9500 . ?
C10 C12 1.503(3) . ?
C10 O2 1.211(2) . ?
C12 C4 1.372(3) . ?
C3 C4 1.409(3) . ?
C4 H4A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C16 1.497(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C8 O5 H5 109.5 . . ?
C1 O3 H3 109.5 . . ?
C3 O4 H4 110.9(16) . . ?
C16 O6 H6 109.5 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.30(18) . . ?
C3 C2 H2 119.9 . . ?
O3 C1 C2 117.94(18) . . ?
O3 C1 C11 121.09(19) . . ?
C2 C1 C11 120.97(19) . . ?
C1 C11 C9 120.79(18) . . ?
C12 C11 C1 117.64(19) . . ?
C12 C11 C9 121.56(18) . . ?
O1 C9 C11 120.64(18) . . ?
O1 C9 C13 120.04(19) . . ?
C11 C9 C13 119.32(18) . . ?
C8 C13 C9 120.69(18) . . ?
C8 C13 C14 118.42(18) . . ?
C14 C13 C9 120.89(19) . . ?
O5 C8 C13 122.46(18) . . ?
O5 C8 C7 117.74(19) . . ?
C7 C8 C13 119.79(19) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 C8 121.6(2) . . ?
C6 C7 H7 119.2 . . ?
C7 C6 C15 120.18(19) . . ?
C7 C6 C5 119.06(19) . . ?
C5 C6 C15 120.76(18) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 C10 120.41(18) . . ?
C5 C14 C13 120.5(2) . . ?
C5 C14 C10 119.04(18) . . ?
C6 C5 H5A 119.7 . . ?
C14 C5 C6 120.50(19) . . ?
C14 C5 H5A 119.7 . . ?
C14 C10 C12 117.79(17) . . ?
O2 C10 C14 121.65(18) . . ?
O2 C10 C12 120.56(19) . . ?
C11 C12 C10 120.00(19) . . ?
C4 C12 C11 121.46(18) . . ?
C4 C12 C10 118.54(18) . . ?
O4 C3 C2 123.34(19) . . ?
O4 C3 C4 117.09(19) . . ?
C2 C3 C4 119.58(19) . . ?
C12 C4 C3 120.05(19) . . ?
C12 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
O6 C16 C17 112.5(2) . . ?
O6 C16 H16A 109.1 . . ?
O6 C16 H16B 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C8 C7 C6 -178.64(18) . . . . ?
O1 C9 C13 C8 0.2(3) . . . . ?
O1 C9 C13 C14 179.85(17) . . . . ?
O3 C1 C11 C9 -1.4(3) . . . . ?
O3 C1 C11 C12 179.51(17) . . . . ?
O4 C3 C4 C12 179.80(18) . . . . ?
C2 C1 C11 C9 179.00(18) . . . . ?
C2 C1 C11 C12 -0.1(3) . . . . ?
C2 C3 C4 C12 -0.2(3) . . . . ?
C1 C2 C3 O4 -179.31(18) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C11 C9 O1 -0.5(3) . . . . ?
C1 C11 C9 C13 179.58(18) . . . . ?
C1 C11 C12 C10 -179.04(17) . . . . ?
C1 C11 C12 C4 0.5(3) . . . . ?
C11 C9 C13 C8 -179.94(17) . . . . ?
C11 C9 C13 C14 -0.3(3) . . . . ?
C11 C12 C4 C3 -0.4(3) . . . . ?
C9 C11 C12 C10 1.9(3) . . . . ?
C9 C11 C12 C4 -178.50(18) . . . . ?
C9 C13 C8 O5 -2.3(3) . . . . ?
C9 C13 C8 C7 177.96(18) . . . . ?
C9 C13 C14 C5 -178.94(18) . . . . ?
C9 C13 C14 C10 1.3(3) . . . . ?
C13 C8 C7 C6 1.2(3) . . . . ?
C13 C14 C5 C6 0.8(3) . . . . ?
C13 C14 C10 C12 -0.8(3) . . . . ?
C13 C14 C10 O2 179.43(19) . . . . ?
C8 C13 C14 C5 0.7(3) . . . . ?
C8 C13 C14 C10 -178.99(17) . . . . ?
C8 C7 C6 C15 179.97(19) . . . . ?
C8 C7 C6 C5 0.4(3) . . . . ?
C7 C6 C5 C14 -1.4(3) . . . . ?
C15 C6 C5 C14 179.04(19) . . . . ?
C14 C13 C8 O5 178.07(17) . . . . ?
C14 C13 C8 C7 -1.7(3) . . . . ?
C14 C10 C12 C11 -0.8(3) . . . . ?
C14 C10 C12 C4 179.59(18) . . . . ?
C5 C14 C10 C12 179.46(18) . . . . ?
C5 C14 C10 O2 -0.3(3) . . . . ?
C10 C14 C5 C6 -179.44(18) . . . . ?
C10 C12 C4 C3 179.16(18) . . . . ?
C12 C11 C9 O1 178.48(17) . . . . ?
C12 C11 C9 C13 -1.4(3) . . . . ?
C3 C2 C1 O3 179.86(17) . . . . ?
C3 C2 C1 C11 -0.6(3) . . . . ?
O2 C10 C12 C11 178.96(19) . . . . ?
O2 C10 C12 C4 -0.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7

_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_mo_2015136_0m
_database_code_depnum_ccdc_archive 'CCDC 1522575'
_audit_update_record             
;
2016-12-14 deposited with the CCDC.
2017-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-11-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 O5, C H4 O'
_chemical_formula_sum            'C16 H14 O6'
_chemical_formula_weight         302.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8735(5)
_cell_length_b                   15.890(2)
_cell_length_c                   21.215(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.664(6)
_cell_angle_gamma                90
_cell_volume                     1304.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1512
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1248 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.6313.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0691
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11373
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_min         1.602
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1273
_reflns_number_total             2957
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'SMART (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2957
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1694
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.147
_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)+(0.1123P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1726
_refine_ls_wR_factor_ref         0.2248
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H6-O6
 1.54 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C2(H2), C5(H5A), C7(H7)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
3.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O6(H6)
;
_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
O4 O -0.4800(8) 0.78159(18) 0.25250(11) 0.0666(9) Uani 1 1 d . . . . .
H4 H -0.5203 0.7301 0.2571 0.100 Uiso 1 1 calc GR . . . .
O5 O 0.4692(8) 0.86357(15) -0.09407(12) 0.0562(8) Uani 1 1 d . . . . .
H5 H 0.408(13) 0.897(3) -0.062(2) 0.084 Uiso 1 1 d R . . . .
O3 O -0.0605(8) 0.97235(14) 0.10773(12) 0.0621(9) Uani 1 1 d . . . . .
H3 H 0.0269 0.9747 0.0723 0.093 Uiso 1 1 calc GR . . . .
O2 O -0.0271(7) 0.59677(14) 0.08008(11) 0.0517(7) Uani 1 1 d . . . . .
O1 O 0.2075(7) 0.91610(13) 0.00817(11) 0.0531(8) Uani 1 1 d . . . . .
O6 O 0.0420(15) 0.1285(3) 0.21326(17) 0.142(2) Uani 1 1 d D . . . .
H6 H 0.0533 0.1256 0.1739 0.213 Uiso 1 1 calc DGR . . . .
C3 C -0.3276(10) 0.7942(3) 0.19661(15) 0.0507(11) Uani 1 1 d . . . . .
C4 C -0.2367(9) 0.7259(2) 0.15854(15) 0.0422(9) Uani 1 1 d . . . . .
H4A H -0.2825 0.6698 0.1712 0.051 Uiso 1 1 calc R . . . .
C12 C -0.0804(9) 0.7414(2) 0.10267(14) 0.0349(8) Uani 1 1 d . . . . .
C10 C 0.0212(9) 0.66917(19) 0.06305(14) 0.0345(8) Uani 1 1 d . . . . .
C14 C 0.1799(8) 0.68719(19) 0.00236(14) 0.0317(8) Uani 1 1 d . . . . .
C13 C 0.2431(9) 0.77124(18) -0.01544(14) 0.0338(8) Uani 1 1 d . . . . .
C8 C 0.3943(9) 0.78530(19) -0.07298(15) 0.0372(9) Uani 1 1 d . . . . .
C2 C -0.2670(11) 0.8746(2) 0.17861(17) 0.0519(11) Uani 1 1 d . . . . .
H2 H -0.3311 0.9198 0.2050 0.062 Uiso 1 1 calc R . . . .
C1 C -0.1148(10) 0.8918(2) 0.12301(16) 0.0463(10) Uani 1 1 d . . . . .
C11 C -0.0169(9) 0.82431(19) 0.08321(15) 0.0368(9) Uani 1 1 d . . . . .
C5 C 0.2672(9) 0.62161(19) -0.03626(15) 0.0356(8) Uani 1 1 d . . . . .
H5A H 0.2261 0.5654 -0.0234 0.043 Uiso 1 1 calc R . . . .
C6 C 0.4153(9) 0.63634(19) -0.09411(15) 0.0375(9) Uani 1 1 d . . . . .
C15 C 0.5044(10) 0.5654(2) -0.13634(16) 0.0476(10) Uani 1 1 d . . . . .
H15A H 0.6514 0.5862 -0.1693 0.071 Uiso 1 1 calc GR . . . .
H15B H 0.2919 0.5415 -0.1558 0.071 Uiso 1 1 calc GR . . . .
H15C H 0.6283 0.5219 -0.1116 0.071 Uiso 1 1 calc GR . . . .
C7 C 0.4786(9) 0.7185(2) -0.11123(15) 0.0411(9) Uani 1 1 d . . . . .
H7 H 0.5824 0.7294 -0.1501 0.049 Uiso 1 1 calc R . . . .
C9 C 0.1468(9) 0.8411(2) 0.02482(15) 0.0378(9) Uani 1 1 d . . . . .
C16 C 0.2402(16) 0.0696(3) 0.2401(3) 0.0995(19) Uani 1 1 d . . . . .
H16A H 0.4702 0.0718 0.2228 0.149 Uiso 1 1 calc GR . . . .
H16B H 0.1371 0.0142 0.2316 0.149 Uiso 1 1 calc GR . . . .
H16C H 0.2603 0.0792 0.2857 0.149 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
O4 H4 0.8400 . ?
O4 C3 1.364(4) . ?
O5 H5 0.90(4) . ?
O5 C8 1.358(4) . ?
O3 H3 0.8400 . ?
O3 C1 1.339(4) . ?
O2 C10 1.223(3) . ?
O1 C9 1.269(4) . ?
O6 H6 0.8400 . ?
O6 C16 1.322(6) . ?
C3 C4 1.407(5) . ?
C3 C2 1.358(5) . ?
C4 H4A 0.9500 . ?
C4 C12 1.378(5) . ?
C12 C10 1.487(5) . ?
C12 C11 1.406(4) . ?
C10 C14 1.480(5) . ?
C14 C13 1.412(4) . ?
C14 C5 1.377(4) . ?
C13 C8 1.396(5) . ?
C13 C9 1.459(4) . ?
C8 C7 1.384(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.370(6) . ?
C1 C11 1.427(5) . ?
C11 C9 1.442(5) . ?
C5 H5A 0.9500 . ?
C5 C6 1.398(5) . ?
C6 C15 1.490(4) . ?
C6 C7 1.380(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C7 H7 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C3 O4 H4 109.5 . . ?
C8 O5 H5 103(3) . . ?
C1 O3 H3 109.5 . . ?
C16 O6 H6 109.5 . . ?
O4 C3 C4 121.1(4) . . ?
C2 C3 O4 118.0(3) . . ?
C2 C3 C4 120.9(3) . . ?
C3 C4 H4A 120.4 . . ?
C12 C4 C3 119.2(3) . . ?
C12 C4 H4A 120.4 . . ?
C4 C12 C10 119.1(3) . . ?
C4 C12 C11 120.7(3) . . ?
C11 C12 C10 120.2(3) . . ?
O2 C10 C12 120.8(3) . . ?
O2 C10 C14 121.0(3) . . ?
C14 C10 C12 118.3(3) . . ?
C13 C14 C10 120.0(3) . . ?
C5 C14 C10 119.6(3) . . ?
C5 C14 C13 120.4(3) . . ?
C14 C13 C9 120.7(3) . . ?
C8 C13 C14 118.0(3) . . ?
C8 C13 C9 121.3(3) . . ?
O5 C8 C13 122.6(3) . . ?
O5 C8 C7 116.7(3) . . ?
C7 C8 C13 120.6(3) . . ?
C3 C2 H2 119.4 . . ?
C3 C2 C1 121.1(3) . . ?
C1 C2 H2 119.4 . . ?
O3 C1 C2 118.5(3) . . ?
O3 C1 C11 121.7(3) . . ?
C2 C1 C11 119.8(3) . . ?
C12 C11 C1 118.4(3) . . ?
C12 C11 C9 121.0(3) . . ?
C1 C11 C9 120.6(3) . . ?
C14 C5 H5A 119.4 . . ?
C14 C5 C6 121.2(3) . . ?
C6 C5 H5A 119.4 . . ?
C5 C6 C15 121.1(3) . . ?
C7 C6 C5 118.3(3) . . ?
C7 C6 C15 120.6(3) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C7 H7 119.3 . . ?
C6 C7 C8 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
O1 C9 C13 119.7(3) . . ?
O1 C9 C11 120.5(3) . . ?
C11 C9 C13 119.8(3) . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C3 C4 C12 -179.4(3) . . . . ?
O4 C3 C2 C1 -180.0(3) . . . . ?
O5 C8 C7 C6 179.7(3) . . . . ?
O3 C1 C11 C12 179.6(3) . . . . ?
O3 C1 C11 C9 0.3(5) . . . . ?
O2 C10 C14 C13 -178.0(3) . . . . ?
O2 C10 C14 C5 1.5(5) . . . . ?
C3 C4 C12 C10 178.9(3) . . . . ?
C3 C4 C12 C11 -1.0(5) . . . . ?
C3 C2 C1 O3 -179.8(3) . . . . ?
C3 C2 C1 C11 -0.2(6) . . . . ?
C4 C3 C2 C1 -0.2(6) . . . . ?
C4 C12 C10 O2 -1.3(5) . . . . ?
C4 C12 C10 C14 178.3(3) . . . . ?
C4 C12 C11 C1 0.7(5) . . . . ?
C4 C12 C11 C9 180.0(3) . . . . ?
C12 C10 C14 C13 2.4(4) . . . . ?
C12 C10 C14 C5 -178.1(3) . . . . ?
C12 C11 C9 O1 -178.9(3) . . . . ?
C12 C11 C9 C13 1.1(5) . . . . ?
C10 C12 C11 C1 -179.3(3) . . . . ?
C10 C12 C11 C9 0.0(5) . . . . ?
C10 C14 C13 C8 179.8(3) . . . . ?
C10 C14 C13 C9 -1.3(4) . . . . ?
C10 C14 C5 C6 179.6(3) . . . . ?
C14 C13 C8 O5 -179.2(3) . . . . ?
C14 C13 C8 C7 0.0(5) . . . . ?
C14 C13 C9 O1 179.6(3) . . . . ?
C14 C13 C9 C11 -0.4(4) . . . . ?
C14 C5 C6 C15 -179.0(3) . . . . ?
C14 C5 C6 C7 1.3(5) . . . . ?
C13 C14 C5 C6 -0.9(5) . . . . ?
C13 C8 C7 C6 0.3(5) . . . . ?
C8 C13 C9 O1 -1.5(5) . . . . ?
C8 C13 C9 C11 178.4(3) . . . . ?
C2 C3 C4 C12 0.8(5) . . . . ?
C2 C1 C11 C12 0.0(5) . . . . ?
C2 C1 C11 C9 -179.4(3) . . . . ?
C1 C11 C9 O1 0.3(5) . . . . ?
C1 C11 C9 C13 -179.6(3) . . . . ?
C11 C12 C10 O2 178.7(3) . . . . ?
C11 C12 C10 C14 -1.8(4) . . . . ?
C5 C14 C13 C8 0.2(5) . . . . ?
C5 C14 C13 C9 179.1(3) . . . . ?
C5 C6 C7 C8 -1.0(5) . . . . ?
C15 C6 C7 C8 179.3(3) . . . . ?
C9 C13 C8 O5 1.9(5) . . . . ?
C9 C13 C8 C7 -178.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
