# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2015538_0m
_database_code_depnum_ccdc_archive 'CCDC 1482005'
_audit_update_record             
;
2016-08-11 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2016-07-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 O5'
_chemical_formula_sum            'C15 H10 O5'
_chemical_formula_weight         270.23
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.783(4)
_cell_length_b                   4.6822(8)
_cell_length_c                   20.212(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.891(8)
_cell_angle_gamma                90
_cell_volume                     2302.0(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2205
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.929
_cell_measurement_theta_min      3.011
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.4268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1363 before and 0.0881 after correction.
The Ratio of minimum to maximum transmission is 0.5728.
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    1.559
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.4
_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  0.0895
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13040
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        24.381
_diffrn_reflns_theta_max         24.381
_diffrn_reflns_theta_min         1.674
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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                1098
_reflns_number_total             1875
_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         0.374
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.062
_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)+(0.0825P)²+1.8799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1748
_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:
 C7(H7), C5(H5A), C4(H4A), C2(H2)
2.b 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
O4 O 0.49069(10) 1.1957(6) 0.33220(13) 0.0439(8) Uani 1 1 d . . . . .
H4 H 0.4744(16) 1.280(9) 0.364(2) 0.066 Uiso 1 1 d R . . . .
O5 O 0.73311(9) -0.0672(6) 0.57707(14) 0.0405(7) Uani 1 1 d . . . . .
H5 H 0.7274(17) 0.028(10) 0.537(2) 0.061 Uiso 1 1 d R . . . .
O2 O 0.55157(9) 0.6405(5) 0.57336(12) 0.0406(7) Uani 1 1 d . . . . .
O3 O 0.63607(10) 0.6264(6) 0.35056(14) 0.0430(8) Uani 1 1 d . . . . .
H3 H 0.6569(18) 0.504(10) 0.377(2) 0.064 Uiso 1 1 d R . . . .
O1 O 0.68596(9) 0.2912(5) 0.46656(12) 0.0385(7) Uani 1 1 d . . . . .
C7 C 0.70094(13) -0.0867(8) 0.6647(2) 0.0369(9) Uani 1 1 d . . . . .
H7 H 0.7276 -0.2306 0.6906 0.044 Uiso 1 1 calc R . . . .
C6 C 0.66692(13) -0.0038(8) 0.69291(19) 0.0371(9) Uani 1 1 d . . . . .
C5 C 0.62767(13) 0.2106(8) 0.65322(19) 0.0359(9) Uani 1 1 d . . . . .
H5A H 0.6037 0.2730 0.6715 0.043 Uiso 1 1 calc R . . . .
C12 C 0.62347(13) 0.3305(8) 0.58873(18) 0.0311(9) Uani 1 1 d . . . . .
C10 C 0.58085(13) 0.5531(8) 0.54760(17) 0.0289(9) Uani 1 1 d . . . . .
C14 C 0.57542(13) 0.6699(8) 0.47650(18) 0.0278(8) Uani 1 1 d . . . . .
C4 C 0.53520(13) 0.8709(8) 0.43757(18) 0.0321(9) Uani 1 1 d . . . . .
H4A H 0.5110 0.9278 0.4559 0.039 Uiso 1 1 calc R . . . .
C3 C 0.53004(13) 0.9910(8) 0.37116(18) 0.0327(9) Uani 1 1 d . . . . .
C8 C 0.69775(13) 0.0325(8) 0.59955(19) 0.0328(9) Uani 1 1 d . . . . .
C11 C 0.65843(12) 0.2458(8) 0.55983(18) 0.0291(9) Uani 1 1 d . . . . .
C15 C 0.67049(14) -0.1283(9) 0.76229(19) 0.0424(11) Uani 1 1 d . . . . .
H15A H 0.6962 -0.2895 0.7789 0.064 Uiso 1 1 calc GR . . . .
H15B H 0.6341 -0.1951 0.7519 0.064 Uiso 1 1 calc GR . . . .
H15C H 0.6836 0.0171 0.8021 0.064 Uiso 1 1 calc GR . . . .
C13 C 0.61128(12) 0.5792(7) 0.44946(17) 0.0274(8) Uani 1 1 d . . . . .
C1 C 0.60455(13) 0.6990(8) 0.38133(18) 0.0315(9) Uani 1 1 d . . . . .
C2 C 0.56392(13) 0.9057(8) 0.34309(18) 0.0345(9) Uani 1 1 d . . . . .
H2 H 0.5598 0.9870 0.2976 0.041 Uiso 1 1 calc R . . . .
C9 C 0.65404(13) 0.3686(7) 0.49080(18) 0.0302(9) 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
O4 H4 1.03(4) . ?
O4 C3 1.379(4) . ?
O5 H5 0.88(4) . ?
O5 C8 1.349(4) . ?
O2 C10 1.229(3) . ?
O3 H3 0.81(5) . ?
O3 C1 1.340(4) . ?
O1 C9 1.256(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.375(5) . ?
C7 C8 1.393(5) . ?
C6 C5 1.412(5) . ?
C6 C15 1.477(5) . ?
C5 H5A 0.9500 . ?
C5 C12 1.371(5) . ?
C12 C10 1.493(5) . ?
C12 C11 1.411(4) . ?
C10 C14 1.476(5) . ?
C14 C4 1.380(5) . ?
C14 C13 1.413(4) . ?
C4 H4A 0.9500 . ?
C4 C3 1.397(5) . ?
C3 C2 1.372(4) . ?
C8 C11 1.410(5) . ?
C11 C9 1.459(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C13 C1 1.413(4) . ?
C13 C9 1.457(5) . ?
C1 C2 1.402(5) . ?
C2 H2 0.9500 . ?

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 112(2) . . ?
C8 O5 H5 108(3) . . ?
C1 O3 H3 107(3) . . ?
C6 C7 H7 118.8 . . ?
C6 C7 C8 122.4(4) . . ?
C8 C7 H7 118.8 . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 C15 122.5(3) . . ?
C5 C6 C15 119.9(3) . . ?
C6 C5 H5A 119.4 . . ?
C12 C5 C6 121.2(3) . . ?
C12 C5 H5A 119.4 . . ?
C5 C12 C10 119.7(3) . . ?
C5 C12 C11 121.3(3) . . ?
C11 C12 C10 119.0(3) . . ?
O2 C10 C12 120.4(3) . . ?
O2 C10 C14 120.8(3) . . ?
C14 C10 C12 118.8(3) . . ?
C4 C14 C10 118.8(3) . . ?
C4 C14 C13 120.8(3) . . ?
C13 C14 C10 120.4(3) . . ?
C14 C4 H4A 120.0 . . ?
C14 C4 C3 120.1(3) . . ?
C3 C4 H4A 120.0 . . ?
O4 C3 C4 120.9(3) . . ?
C2 C3 O4 118.6(3) . . ?
C2 C3 C4 120.5(3) . . ?
O5 C8 C7 117.1(3) . . ?
O5 C8 C11 122.9(3) . . ?
C7 C8 C11 120.0(3) . . ?
C12 C11 C9 121.9(3) . . ?
C8 C11 C12 117.5(3) . . ?
C8 C11 C9 120.5(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 . . ?
C14 C13 C9 120.9(3) . . ?
C1 C13 C14 118.1(3) . . ?
C1 C13 C9 121.0(3) . . ?
O3 C1 C13 122.9(3) . . ?
O3 C1 C2 116.9(3) . . ?
C2 C1 C13 120.2(3) . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
O1 C9 C11 120.7(3) . . ?
O1 C9 C13 120.4(3) . . ?
C13 C9 C11 118.9(3) . . ?

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 C2 C1 179.7(3) . . . . ?
O5 C8 C11 C12 179.5(3) . . . . ?
O5 C8 C11 C9 0.5(5) . . . . ?
O2 C10 C14 C4 -2.7(5) . . . . ?
O2 C10 C14 C13 176.6(3) . . . . ?
O3 C1 C2 C3 180.0(3) . . . . ?
C7 C6 C5 C12 0.3(5) . . . . ?
C7 C8 C11 C12 0.1(5) . . . . ?
C7 C8 C11 C9 -178.9(3) . . . . ?
C6 C7 C8 O5 -179.6(3) . . . . ?
C6 C7 C8 C11 -0.2(5) . . . . ?
C6 C5 C12 C10 179.0(3) . . . . ?
C6 C5 C12 C11 -0.5(5) . . . . ?
C5 C12 C10 O2 4.0(5) . . . . ?
C5 C12 C10 C14 -177.3(3) . . . . ?
C5 C12 C11 C8 0.2(5) . . . . ?
C5 C12 C11 C9 179.2(3) . . . . ?
C12 C10 C14 C4 178.5(3) . . . . ?
C12 C10 C14 C13 -2.2(5) . . . . ?
C12 C11 C9 O1 179.4(3) . . . . ?
C12 C11 C9 C13 -1.7(5) . . . . ?
C10 C12 C11 C8 -179.2(3) . . . . ?
C10 C12 C11 C9 -0.2(5) . . . . ?
C10 C14 C4 C3 178.3(3) . . . . ?
C10 C14 C13 C1 -179.6(3) . . . . ?
C10 C14 C13 C9 0.3(5) . . . . ?
C14 C4 C3 O4 -178.9(3) . . . . ?
C14 C4 C3 C2 1.5(5) . . . . ?
C14 C13 C1 O3 -179.5(3) . . . . ?
C14 C13 C1 C2 1.2(5) . . . . ?
C14 C13 C9 O1 -179.5(3) . . . . ?
C14 C13 C9 C11 1.7(5) . . . . ?
C4 C14 C13 C1 -0.3(5) . . . . ?
C4 C14 C13 C9 179.5(3) . . . . ?
C4 C3 C2 C1 -0.7(5) . . . . ?
C8 C7 C6 C5 0.0(5) . . . . ?
C8 C7 C6 C15 -179.5(3) . . . . ?
C8 C11 C9 O1 -1.6(5) . . . . ?
C8 C11 C9 C13 177.3(3) . . . . ?
C11 C12 C10 O2 -176.6(3) . . . . ?
C11 C12 C10 C14 2.2(5) . . . . ?
C15 C6 C5 C12 179.9(3) . . . . ?
C13 C14 C4 C3 -1.0(5) . . . . ?
C13 C1 C2 C3 -0.7(5) . . . . ?
C1 C13 C9 O1 0.4(5) . . . . ?
C1 C13 C9 C11 -178.4(3) . . . . ?
C9 C13 C1 O3 0.6(5) . . . . ?
C9 C13 C1 C2 -178.7(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_2015535_0m_sq_s
_database_code_depnum_ccdc_archive 'CCDC 1482006'
_audit_update_record             
;
2016-08-15 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O5'
_chemical_formula_sum            'C15 H10 O5'
_chemical_formula_weight         270.23
_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                   16.4721(10)
_cell_length_b                   3.6915(2)
_cell_length_c                   19.4294(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.188(4)
_cell_angle_gamma                90
_cell_volume                     1174.56(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1570
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             565
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12341
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.510
_diffrn_reflns_theta_max         24.510
_diffrn_reflns_theta_min         1.541
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_radiation_type           MoK\a

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                909
_reflns_number_total             1954
_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       '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    ?
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         1954
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.1845
_refine_ls_R_factor_gt           0.0907
_refine_ls_restrained_S_all      1.103
_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)+(0.1638P)²+1.3269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2232
_refine_ls_wR_factor_ref         0.3060
_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, C3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C1, C11
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C4, C3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C1 \\sim C11: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
O4 \\sim C3: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
C3 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C9) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(O3) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O2) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4A), C5(H5A), C7(H7)
4.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
4.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3), O5(H5)
;
_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
O4 O -0.1055(3) 1.2511(13) 0.3426(2) 0.0584(13) Uani 1 1 d . U . . .
H4 H -0.1205 1.2925 0.3819 0.088 Uiso 1 1 calc GR . . . .
O3 O 0.1220(3) 0.7445(12) 0.24491(19) 0.0468(13) Uani 1 1 d . U . . .
H3 H 0.1724 0.7081 0.2530 0.070 Uiso 1 1 calc GR . . . .
O1 O 0.2602(2) 0.7081(11) 0.32131(19) 0.0429(12) Uani 1 1 d . U . . .
O2 O 0.1264(2) 1.3367(10) 0.53294(19) 0.0388(12) Uani 1 1 d . U . . .
O5 O 0.3989(2) 0.6323(12) 0.3990(2) 0.0485(13) Uani 1 1 d . U . . .
H5 H 0.3676 0.6274 0.3619 0.073 Uiso 1 1 calc GR . . . .
C2 C 0.0122(4) 0.9930(17) 0.2952(3) 0.0419(16) Uani 1 1 d . U . . .
H2 H -0.0207 0.9563 0.2525 0.050 Uiso 1 1 calc R . . . .
C3 C -0.0223(4) 1.1439(17) 0.3501(3) 0.0410(12) Uani 1 1 d . U . . .
C4 C 0.0251(3) 1.1954(16) 0.4128(3) 0.0376(12) Uani 1 1 d . U . . .
H4A H 0.0013 1.2928 0.4512 0.045 Uiso 1 1 calc R . . . .
C12 C 0.1067(3) 1.1049(14) 0.4194(3) 0.0261(13) Uani 1 1 d . U . . .
C10 C 0.1562(3) 1.1717(15) 0.4866(3) 0.0302(14) Uani 1 1 d . U . . .
C14 C 0.2418(3) 1.0472(15) 0.4955(3) 0.0281(14) Uani 1 1 d . U . . .
C5 C 0.2869(4) 1.0803(16) 0.5584(3) 0.0373(15) Uani 1 1 d . U . . .
H5A H 0.2627 1.1823 0.5962 0.045 Uiso 1 1 calc R . . . .
C6 C 0.3690(4) 0.9650(18) 0.5680(3) 0.0482(18) Uani 1 1 d . U . . .
C15 C 0.4149(4) 1.0194(19) 0.6352(3) 0.0565(19) Uani 1 1 d . . . . .
H15A H 0.4676 0.8955 0.6365 0.085 Uiso 1 1 calc GR . . . .
H15B H 0.3841 0.9203 0.6713 0.085 Uiso 1 1 calc GR . . . .
H15C H 0.4239 1.2791 0.6431 0.085 Uiso 1 1 calc GR . . . .
C11 C 0.1432(3) 0.9455(15) 0.3640(3) 0.0298(12) Uani 1 1 d . U . . .
C1 C 0.0939(3) 0.8937(15) 0.3010(3) 0.0320(12) Uani 1 1 d . U . . .
C9 C 0.2288(3) 0.8434(15) 0.3723(3) 0.0319(15) Uani 1 1 d . U . . .
C13 C 0.2763(3) 0.8895(15) 0.4382(3) 0.0298(14) Uani 1 1 d . U . . .
C7 C 0.4031(4) 0.8207(17) 0.5131(3) 0.0445(17) Uani 1 1 d . U . . .
H7 H 0.4587 0.7470 0.5192 0.053 Uiso 1 1 calc R . . . .
C8 C 0.3594(3) 0.7790(16) 0.4493(3) 0.0356(15) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 H4 0.8400 . ?
O4 C3 1.419(7) . ?
O3 H3 0.8400 . ?
O3 C1 1.346(6) . ?
O1 C9 1.268(6) . ?
O2 C10 1.232(6) . ?
O5 H5 0.8400 . ?
O5 C8 1.345(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(8) . ?
C2 C1 1.388(8) . ?
C3 C4 1.388(8) . ?
C4 H4A 0.9500 . ?
C4 C12 1.379(7) . ?
C12 C10 1.483(7) . ?
C12 C11 1.416(7) . ?
C10 C14 1.477(7) . ?
C14 C5 1.367(8) . ?
C14 C13 1.426(7) . ?
C5 H5A 0.9500 . ?
C5 C6 1.411(8) . ?
C6 C15 1.449(8) . ?
C6 C7 1.366(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C11 C1 1.407(8) . ?
C11 C9 1.452(7) . ?
C9 C13 1.437(8) . ?
C13 C8 1.423(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(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
C3 O4 H4 109.5 . . ?
C1 O3 H3 109.5 . . ?
C8 O5 H5 109.5 . . ?
C3 C2 H2 119.3 . . ?
C3 C2 C1 121.4(5) . . ?
C1 C2 H2 119.3 . . ?
C2 C3 O4 120.5(6) . . ?
C2 C3 C4 119.7(6) . . ?
C4 C3 O4 119.8(5) . . ?
C3 C4 H4A 120.0 . . ?
C12 C4 C3 119.9(5) . . ?
C12 C4 H4A 120.0 . . ?
C4 C12 C10 118.6(5) . . ?
C4 C12 C11 121.3(5) . . ?
C11 C12 C10 120.1(5) . . ?
O2 C10 C12 120.1(5) . . ?
O2 C10 C14 121.3(5) . . ?
C14 C10 C12 118.5(5) . . ?
C5 C14 C10 119.8(5) . . ?
C5 C14 C13 120.8(5) . . ?
C13 C14 C10 119.5(5) . . ?
C14 C5 H5A 119.6 . . ?
C14 C5 C6 120.8(5) . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C15 118.4(6) . . ?
C7 C6 C5 118.9(6) . . ?
C7 C6 C15 122.7(6) . . ?
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 . . ?
C12 C11 C9 120.6(5) . . ?
C1 C11 C12 117.7(5) . . ?
C1 C11 C9 121.6(5) . . ?
O3 C1 C2 117.2(5) . . ?
O3 C1 C11 122.9(5) . . ?
C2 C1 C11 119.9(5) . . ?
O1 C9 C11 119.2(5) . . ?
O1 C9 C13 121.0(5) . . ?
C13 C9 C11 119.8(5) . . ?
C14 C13 C9 121.3(5) . . ?
C8 C13 C14 117.1(5) . . ?
C8 C13 C9 121.5(5) . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.0(6) . . ?
C8 C7 H7 119.0 . . ?
O5 C8 C13 122.5(5) . . ?
O5 C8 C7 117.0(5) . . ?
C7 C8 C13 120.5(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 -177.4(5) . . . . ?
O1 C9 C13 C14 178.9(5) . . . . ?
O1 C9 C13 C8 -1.3(8) . . . . ?
O2 C10 C14 C5 7.0(8) . . . . ?
O2 C10 C14 C13 -173.8(5) . . . . ?
C2 C3 C4 C12 1.8(9) . . . . ?
C3 C2 C1 O3 179.2(5) . . . . ?
C3 C2 C1 C11 0.2(9) . . . . ?
C3 C4 C12 C10 178.5(5) . . . . ?
C3 C4 C12 C11 -2.6(8) . . . . ?
C4 C12 C10 O2 -7.0(8) . . . . ?
C4 C12 C10 C14 175.0(5) . . . . ?
C4 C12 C11 C1 2.2(8) . . . . ?
C4 C12 C11 C9 -178.4(5) . . . . ?
C12 C10 C14 C5 -175.1(5) . . . . ?
C12 C10 C14 C13 4.2(8) . . . . ?
C12 C11 C1 O3 -179.9(5) . . . . ?
C12 C11 C1 C2 -0.9(8) . . . . ?
C12 C11 C9 O1 -178.6(5) . . . . ?
C12 C11 C9 C13 2.7(8) . . . . ?
C10 C12 C11 C1 -179.0(5) . . . . ?
C10 C12 C11 C9 0.5(8) . . . . ?
C10 C14 C5 C6 -179.7(5) . . . . ?
C10 C14 C13 C9 -1.1(8) . . . . ?
C10 C14 C13 C8 179.1(5) . . . . ?
C14 C5 C6 C15 177.7(5) . . . . ?
C14 C5 C6 C7 0.3(9) . . . . ?
C14 C13 C8 O5 -178.9(5) . . . . ?
C14 C13 C8 C7 0.9(8) . . . . ?
C5 C14 C13 C9 178.2(5) . . . . ?
C5 C14 C13 C8 -1.6(8) . . . . ?
C5 C6 C7 C8 -1.2(10) . . . . ?
C6 C7 C8 O5 -179.7(6) . . . . ?
C6 C7 C8 C13 0.5(9) . . . . ?
C15 C6 C7 C8 -178.4(6) . . . . ?
C11 C12 C10 O2 174.1(5) . . . . ?
C11 C12 C10 C14 -3.9(7) . . . . ?
C11 C9 C13 C14 -2.4(8) . . . . ?
C11 C9 C13 C8 177.4(5) . . . . ?
C1 C2 C3 O4 178.6(5) . . . . ?
C1 C2 C3 C4 -0.6(9) . . . . ?
C1 C11 C9 O1 0.8(8) . . . . ?
C1 C11 C9 C13 -177.8(5) . . . . ?
C9 C11 C1 O3 0.7(8) . . . . ?
C9 C11 C1 C2 179.6(5) . . . . ?
C9 C13 C8 O5 1.3(8) . . . . ?
C9 C13 C8 C7 -179.0(5) . . . . ?
C13 C14 C5 C6 1.1(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_2015467_0m_sq_s
_database_code_depnum_ccdc_archive 'CCDC 1482007'
_audit_update_record             
;
2016-08-18 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O5'
_chemical_formula_sum            'C15 H10 O5'
_chemical_formula_weight         270.23
_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                   12.6343(6)
_cell_length_b                   3.6437(2)
_cell_length_c                   31.2026(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.706(3)
_cell_angle_gamma                90
_cell_volume                     1429.31(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2393
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.962
_cell_measurement_theta_min      2.421
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0942 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.8671.
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    1.256
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            19465
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.449
_diffrn_reflns_theta_max         24.449
_diffrn_reflns_theta_min         1.686
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1354
_reflns_number_total             2367
_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       '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    ?
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.006(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2367
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.069
_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)+(0.0915P)²+0.7811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1967
_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. Shared sites
{O4, C16}
{C15, O15}
3. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O4) = Uanis(C16)
Uanis(C15) = Uanis(O15)
4. Others
 Fixed Sof: O4(0.5) H4(0.5) C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C16(0.5)
 H16A(0.5) H16B(0.5) H16C(0.5) O15(0.5) H15(0.5)
5.a Riding coordinates:
 O4(H4), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), O15(H15)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C5(H5A), C4(H4A)
5.c Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA), O5(H5)
;
_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
O0AA O 0.3381(2) 1.3658(7) 0.19804(7) 0.0735(9) Uani 1 1 d . . . . .
H0AA H 0.3828 1.3211 0.1805 0.110 Uiso 1 1 calc GR . . . .
O2AA O 0.40387(19) 1.1233(7) 0.12811(7) 0.0609(7) Uani 1 1 d . . . . .
O5 O 0.47318(18) 0.8820(8) 0.05863(9) 0.0724(8) Uani 1 1 d . . . . .
H5 H 0.4774 0.9816 0.0830 0.109 Uiso 1 1 calc GR . . . .
O5AA O -0.00021(18) 0.8584(7) 0.06248(7) 0.0535(7) Uani 1 1 d . . . . .
O4 O -0.0387(3) 1.3822(10) 0.20933(12) 0.1042(14) Uani 0.5 1 d . U P A 1
H4 H -0.0191 1.4212 0.2355 0.156 Uiso 0.5 1 d R . P A 1
C15 C 0.2184(3) 0.4792(8) -0.05663(8) 0.0731(11) Uani 0.5 1 d . . P B 1
H15A H 0.2827 0.3826 -0.0677 0.110 Uiso 0.5 1 d R . P B 1
H15B H 0.1882 0.6746 -0.0757 0.110 Uiso 0.5 1 d R . P B 1
H15C H 0.1662 0.2813 -0.0555 0.110 Uiso 0.5 1 d R . P B 1
C6 C 0.2448(3) 0.6250(9) -0.01392(9) 0.0489(9) Uani 1 1 d . . . . .
C7 C 0.3476(3) 0.6870(9) 0.00270(12) 0.0589(11) Uani 1 1 d . . . . .
H7 H 0.4042 0.6334 -0.0142 0.071 Uiso 1 1 calc R . . . .
C8 C 0.3701(3) 0.8290(9) 0.04435(11) 0.0505(9) Uani 1 1 d . . . . .
C13 C 0.2870(2) 0.9089(8) 0.06964(9) 0.0354(7) Uani 1 1 d . . . . .
C9 C 0.3091(3) 1.0615(8) 0.11275(10) 0.0432(9) Uani 1 1 d . . . . .
C11 C 0.2205(3) 1.1452(8) 0.13751(8) 0.0393(8) Uani 1 1 d . . . . .
C1 C 0.2397(3) 1.2921(9) 0.17946(10) 0.0541(10) Uani 1 1 d . . . . .
C2 C 0.1560(4) 1.3691(9) 0.20322(11) 0.0664(12) Uani 1 1 d . . . . .
H2 H 0.1696 1.4674 0.2314 0.080 Uiso 1 1 calc R . . . .
C5 C 0.1616(3) 0.7024(8) 0.01088(9) 0.0400(8) Uani 1 1 d . . . . .
H5A H 0.0903 0.6580 -0.0006 0.048 Uiso 1 1 calc R . . . .
C14 C 0.1817(2) 0.8419(7) 0.05172(8) 0.0323(7) Uani 1 1 d . . . . .
C10 C 0.0921(3) 0.9228(8) 0.07723(9) 0.0351(7) Uani 1 1 d . . . . .
C12 C 0.1154(2) 1.0804(8) 0.12102(8) 0.0357(8) Uani 1 1 d . . . . .
C4 C 0.0325(3) 1.1593(9) 0.14469(10) 0.0518(9) Uani 1 1 d . . . . .
H4A H -0.0387 1.1162 0.1330 0.062 Uiso 1 1 calc R . . . .
C3 C 0.0539(4) 1.3052(10) 0.18655(12) 0.0639(11) Uani 1 1 d . . . . .
C16 C -0.0387(3) 1.3822(10) 0.20933(12) 0.1042(14) Uani 0.5 1 d . . P A 2
H16A H -0.0433 1.6471 0.2143 0.156 Uiso 0.5 1 d R . P A 2
H16B H -0.0316 1.2536 0.2370 0.156 Uiso 0.5 1 d R . P A 2
H16C H -0.1029 1.2983 0.1920 0.156 Uiso 0.5 1 d R . P A 2
O15 O 0.2184(3) 0.4792(8) -0.05663(8) 0.0731(11) Uani 0.5 1 d . . P B 2
H15 H 0.2240 0.2494 -0.0559 0.110 Uiso 0.5 1 d R . P B 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
O0AA H0AA 0.8400 . ?
O0AA C1 1.345(4) . ?
O2AA C9 1.265(4) . ?
O5 H5 0.8400 . ?
O5 C8 1.347(4) . ?
O5AA C10 1.233(3) . ?
O4 H4 0.8400 . ?
O4 C3 1.455(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9799 . ?
C15 H15C 0.9800 . ?
C15 C6 1.443(4) . ?
C6 C7 1.368(5) . ?
C6 C5 1.395(4) . ?
C6 O15 1.443(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(5) . ?
C8 C13 1.406(4) . ?
C13 C9 1.457(4) . ?
C13 C14 1.412(4) . ?
C9 C11 1.454(4) . ?
C11 C1 1.413(4) . ?
C11 C12 1.396(4) . ?
C1 C2 1.380(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.362(5) . ?
C5 H5A 0.9500 . ?
C5 C14 1.372(4) . ?
C14 C10 1.477(4) . ?
C10 C12 1.484(4) . ?
C12 C4 1.371(4) . ?
C4 H4A 0.9500 . ?
C4 C3 1.411(5) . ?
C3 C16 1.455(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9791 . ?
C16 H16C 0.9788 . ?
O15 H15 0.8402 . ?

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 O0AA H0AA 109.5 . . ?
C8 O5 H5 109.5 . . ?
C3 O4 H4 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.4 . . ?
C6 C15 H15C 109.4 . . ?
C7 C6 C15 122.3(3) . . ?
C7 C6 C5 119.7(3) . . ?
C7 C6 O15 122.3(3) . . ?
C5 C6 C15 118.0(3) . . ?
C5 C6 O15 118.0(3) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
O5 C8 C7 117.4(3) . . ?
O5 C8 C13 122.4(3) . . ?
C7 C8 C13 120.1(3) . . ?
C8 C13 C9 120.8(3) . . ?
C8 C13 C14 118.0(3) . . ?
C14 C13 C9 121.2(3) . . ?
O2AA C9 C13 120.3(3) . . ?
O2AA C9 C11 120.7(3) . . ?
C11 C9 C13 118.9(3) . . ?
C1 C11 C9 120.1(3) . . ?
C12 C11 C9 121.5(3) . . ?
C12 C11 C1 118.4(3) . . ?
O0AA C1 C11 122.8(4) . . ?
O0AA C1 C2 116.9(3) . . ?
C2 C1 C11 120.3(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C14 C5 C6 120.7(3) . . ?
C14 C5 H5A 119.7 . . ?
C13 C14 C10 119.6(3) . . ?
C5 C14 C13 120.8(3) . . ?
C5 C14 C10 119.6(3) . . ?
O5AA C10 C14 120.5(3) . . ?
O5AA C10 C12 120.8(3) . . ?
C14 C10 C12 118.7(3) . . ?
C11 C12 C10 120.0(3) . . ?
C4 C12 C11 121.1(3) . . ?
C4 C12 C10 119.0(3) . . ?
C12 C4 H4A 120.3 . . ?
C12 C4 C3 119.5(4) . . ?
C3 C4 H4A 120.3 . . ?
C2 C3 O4 123.9(4) . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 C16 123.9(4) . . ?
C4 C3 O4 115.9(4) . . ?
C4 C3 C16 115.9(4) . . ?
C3 C16 H16A 109.3 . . ?
C3 C16 H16B 109.4 . . ?
C3 C16 H16C 109.4 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.6 . . ?
H16B C16 H16C 109.7 . . ?
C6 O15 H15 109.3 . . ?

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
O0AA C1 C2 C3 179.4(3) . . . . ?
O2AA C9 C11 C1 -1.0(4) . . . . ?
O2AA C9 C11 C12 179.7(3) . . . . ?
O5 C8 C13 C9 1.2(5) . . . . ?
O5 C8 C13 C14 -179.7(3) . . . . ?
O5AA C10 C12 C11 178.8(3) . . . . ?
O5AA C10 C12 C4 -1.1(4) . . . . ?
C15 C6 C7 C8 -180.0(3) . . . . ?
C15 C6 C5 C14 -179.9(3) . . . . ?
C6 C7 C8 O5 179.8(3) . . . . ?
C6 C7 C8 C13 0.1(5) . . . . ?
C6 C5 C14 C13 -0.3(4) . . . . ?
C6 C5 C14 C10 179.8(3) . . . . ?
C7 C6 C5 C14 0.3(4) . . . . ?
C7 C8 C13 C9 -179.1(3) . . . . ?
C7 C8 C13 C14 0.0(4) . . . . ?
C8 C13 C9 O2AA -0.2(4) . . . . ?
C8 C13 C9 C11 179.1(3) . . . . ?
C8 C13 C14 C5 0.1(4) . . . . ?
C8 C13 C14 C10 -179.9(3) . . . . ?
C13 C9 C11 C1 179.8(3) . . . . ?
C13 C9 C11 C12 0.5(4) . . . . ?
C13 C14 C10 O5AA -178.4(3) . . . . ?
C13 C14 C10 C12 1.2(4) . . . . ?
C9 C13 C14 C5 179.2(2) . . . . ?
C9 C13 C14 C10 -0.8(4) . . . . ?
C9 C11 C1 O0AA 1.0(4) . . . . ?
C9 C11 C1 C2 -179.4(3) . . . . ?
C9 C11 C12 C10 -0.1(4) . . . . ?
C9 C11 C12 C4 179.8(3) . . . . ?
C11 C1 C2 C3 -0.1(5) . . . . ?
C11 C12 C4 C3 -0.6(4) . . . . ?
C1 C11 C12 C10 -179.4(3) . . . . ?
C1 C11 C12 C4 0.5(4) . . . . ?
C1 C2 C3 O4 -179.4(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C16 -179.4(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C5 C14 C10 O5AA 1.6(4) . . . . ?
C5 C14 C10 C12 -178.8(2) . . . . ?
C14 C13 C9 O2AA -179.3(3) . . . . ?
C14 C13 C9 C11 0.0(4) . . . . ?
C14 C10 C12 C11 -0.7(4) . . . . ?
C14 C10 C12 C4 179.4(3) . . . . ?
C10 C12 C4 C3 179.3(3) . . . . ?
C12 C11 C1 O0AA -179.6(3) . . . . ?
C12 C11 C1 C2 -0.1(4) . . . . ?
C12 C4 C3 O4 179.8(3) . . . . ?
C12 C4 C3 C2 0.4(5) . . . . ?
C12 C4 C3 C16 179.8(3) . . . . ?
O15 C6 C7 C8 -180.0(3) . . . . ?
O15 C6 C5 C14 -179.9(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 -0.250 -0.781 0.250 157.9 55.1 ?
2 0.250 -0.099 0.750 157.9 55.1 ?

_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_2015505_0m_sq_s
_database_code_depnum_ccdc_archive 'CCDC 1482008'
_audit_update_record             
;
2016-08-15 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 O5'
_chemical_formula_sum            'C15 H10 O5'
_chemical_formula_weight         270.23
_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                   16.6384(6)
_cell_length_b                   3.6887(2)
_cell_length_c                   19.4060(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.544(3)
_cell_angle_gamma                90
_cell_volume                     1185.45(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2177
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.37
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0896 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.8725.
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    1.514
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12962
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.397
_diffrn_reflns_theta_max         24.397
_diffrn_reflns_theta_min         1.540
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                1317
_reflns_number_total             1949
_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       '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    ?
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.072
_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)+(0.1005P)²+2.0877P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1839
_refine_ls_wR_factor_ref         0.2158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H4 of O4
 At 1.5 times of:
  All C(H,H,H) groups, H3 of O3, H5 of O5
2. Rigid bond restraints
 O4, C9
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C13, C14
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C2, C7
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C2 \\sim C7: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(O4) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C7) \\sim
Ueq, Uanis(C13) \\sim Ueq, Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C14(H14), C12(H12)
4.b Tetrahedral OH refined with riding coordinates:
 O4(H4)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O3 O 0.12381(17) 0.2432(8) 0.24522(12) 0.0482(8) Uani 1 1 d . . . A 1
H3 H 0.1728 0.1911 0.2542 0.072 Uiso 1 1 calc GR . . A 1
O4 O -0.10002(17) 0.7489(9) 0.34458(17) 0.0667(10) Uani 1 1 d . U . A 1
H4 H -0.1078 0.9032 0.3751 0.080 Uiso 1 1 calc R . . A 1
O2 O 0.12684(16) 0.8336(7) 0.53385(13) 0.0460(8) Uani 1 1 d . . . A 1
O5 O 0.39690(17) 0.1318(8) 0.39776(17) 0.0542(8) Uani 1 1 d . . . A 1
H5 H 0.362(3) 0.126(16) 0.358(3) 0.081 Uiso 1 1 d R . . B 1
O1 O 0.26042(15) 0.2050(7) 0.32124(12) 0.0441(7) Uani 1 1 d . . . A 1
C8 C 0.0147(2) 0.4945(11) 0.29577(19) 0.0445(10) Uani 1 1 d . . . A 1
H8 H -0.0175 0.4615 0.2531 0.053 Uiso 1 1 calc R . . A 1
C9 C -0.0190(2) 0.6441(10) 0.3515(2) 0.0433(10) Uani 1 1 d . U . A 1
C10 C 0.0277(2) 0.6949(10) 0.41393(19) 0.0373(9) Uani 1 1 d . . . A 1
H10 H 0.0041 0.7956 0.4523 0.045 Uiso 1 1 calc R . . A 1
C3 C 0.1079(2) 0.6006(9) 0.42060(17) 0.0317(8) Uani 1 1 d . . . A 1
C4 C 0.1566(2) 0.6696(9) 0.48710(17) 0.0347(9) Uani 1 1 d . . . A 1
C5 C 0.2413(2) 0.5442(9) 0.49561(18) 0.0360(9) Uani 1 1 d . . . A 1
C14 C 0.2857(2) 0.5818(11) 0.55879(19) 0.0444(9) Uani 1 1 d . U . A 1
H14 H 0.2615 0.6852 0.5966 0.053 Uiso 1 1 calc R . . A 1
C13 C 0.3666(3) 0.4682(12) 0.5678(2) 0.0550(11) Uani 1 1 d . U . A 1
C15 C 0.4116(3) 0.5191(14) 0.6351(2) 0.0692(14) Uani 1 1 d . . . A 1
H15A H 0.4636 0.3939 0.6360 0.104 Uiso 1 1 calc GR . . A 1
H15B H 0.3807 0.4193 0.6712 0.104 Uiso 1 1 calc GR . . A 1
H15C H 0.4208 0.7785 0.6434 0.104 Uiso 1 1 calc GR . . A 1
C7 C 0.0954(2) 0.3917(10) 0.30183(17) 0.0367(8) Uani 1 1 d . U . A 1
C2 C 0.1442(2) 0.4448(9) 0.36440(16) 0.0327(7) Uani 1 1 d . U . A 1
C6 C 0.2759(2) 0.3884(9) 0.43828(18) 0.0352(9) Uani 1 1 d . . . A 1
C11 C 0.3573(2) 0.2799(10) 0.4485(2) 0.0441(10) Uani 1 1 d . . . A 1
C12 C 0.4007(3) 0.3207(11) 0.5122(2) 0.0510(11) Uani 1 1 d . U . A 1
H12 H 0.4556 0.2453 0.5179 0.061 Uiso 1 1 calc R . . A 1
C1 C 0.2289(2) 0.3421(9) 0.37215(18) 0.0344(9) Uani 1 1 d . . . A 1


_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 C7 1.353(4) . ?
O4 H4 0.8400 . ?
O4 C9 1.397(5) . ?
O2 C4 1.233(4) . ?
O5 H5 0.92(5) . ?
O5 C11 1.352(4) . ?
O1 C1 1.268(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.380(5) . ?
C8 C7 1.389(5) . ?
C9 C10 1.387(5) . ?
C10 H10 0.9500 . ?
C10 C3 1.372(5) . ?
C3 C4 1.478(5) . ?
C3 C2 1.418(4) . ?
C4 C5 1.478(5) . ?
C5 C14 1.376(5) . ?
C5 C6 1.422(5) . ?
C14 H14 0.9500 . ?
C14 C13 1.404(6) . ?
C13 C15 1.453(6) . ?
C13 C12 1.379(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C7 C2 1.408(5) . ?
C2 C1 1.453(5) . ?
C6 C11 1.408(5) . ?
C6 C1 1.447(5) . ?
C11 C12 1.378(6) . ?
C12 H12 0.9500 . ?

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
C7 O3 H3 109.5 . . ?
C9 O4 H4 109.5 . . ?
C11 O5 H5 107(3) . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C8 C9 O4 119.8(4) . . ?
C8 C9 C10 120.2(3) . . ?
C10 C9 O4 120.0(3) . . ?
C9 C10 H10 119.8 . . ?
C3 C10 C9 120.4(3) . . ?
C3 C10 H10 119.8 . . ?
C10 C3 C4 119.0(3) . . ?
C10 C3 C2 120.8(3) . . ?
C2 C3 C4 120.2(3) . . ?
O2 C4 C3 120.1(3) . . ?
O2 C4 C5 121.2(3) . . ?
C5 C4 C3 118.7(3) . . ?
C14 C5 C4 119.5(3) . . ?
C14 C5 C6 121.0(3) . . ?
C6 C5 C4 119.5(3) . . ?
C5 C14 H14 119.8 . . ?
C5 C14 C13 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C14 C13 C15 118.5(4) . . ?
C12 C13 C14 118.9(4) . . ?
C12 C13 C15 122.6(4) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C7 C8 116.9(3) . . ?
O3 C7 C2 122.6(3) . . ?
C8 C7 C2 120.5(3) . . ?
C3 C2 C1 120.4(3) . . ?
C7 C2 C3 117.8(3) . . ?
C7 C2 C1 121.8(3) . . ?
C5 C6 C1 121.2(3) . . ?
C11 C6 C5 117.4(3) . . ?
C11 C6 C1 121.4(3) . . ?
O5 C11 C6 122.8(4) . . ?
O5 C11 C12 116.5(4) . . ?
C12 C11 C6 120.6(4) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 C13 121.6(4) . . ?
C11 C12 H12 119.2 . . ?
O1 C1 C2 119.5(3) . . ?
O1 C1 C6 120.7(3) . . ?
C6 C1 C2 119.8(3) . . ?

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 C7 C2 C3 -179.6(3) . . . . ?
O3 C7 C2 C1 -0.1(5) . . . . ?
O4 C9 C10 C3 -178.4(3) . . . . ?
O2 C4 C5 C14 5.9(5) . . . . ?
O2 C4 C5 C6 -173.8(3) . . . . ?
O5 C11 C12 C13 -179.9(4) . . . . ?
C8 C9 C10 C3 0.7(5) . . . . ?
C8 C7 C2 C3 0.9(5) . . . . ?
C8 C7 C2 C1 -179.6(3) . . . . ?
C9 C8 C7 O3 179.3(3) . . . . ?
C9 C8 C7 C2 -1.1(5) . . . . ?
C9 C10 C3 C4 178.0(3) . . . . ?
C9 C10 C3 C2 -1.0(5) . . . . ?
C10 C3 C4 O2 -5.3(5) . . . . ?
C10 C3 C4 C5 175.7(3) . . . . ?
C10 C3 C2 C7 0.2(5) . . . . ?
C10 C3 C2 C1 -179.3(3) . . . . ?
C3 C4 C5 C14 -175.2(3) . . . . ?
C3 C4 C5 C6 5.2(5) . . . . ?
C3 C2 C1 O1 -179.6(3) . . . . ?
C3 C2 C1 C6 2.0(5) . . . . ?
C4 C3 C2 C7 -178.8(3) . . . . ?
C4 C3 C2 C1 1.7(5) . . . . ?
C4 C5 C14 C13 -179.3(3) . . . . ?
C4 C5 C6 C11 178.7(3) . . . . ?
C4 C5 C6 C1 -1.6(5) . . . . ?
C5 C14 C13 C15 178.9(4) . . . . ?
C5 C14 C13 C12 0.4(6) . . . . ?
C5 C6 C11 O5 -179.4(3) . . . . ?
C5 C6 C11 C12 0.8(5) . . . . ?
C5 C6 C1 O1 179.6(3) . . . . ?
C5 C6 C1 C2 -2.1(5) . . . . ?
C14 C5 C6 C11 -0.9(5) . . . . ?
C14 C5 C6 C1 178.8(3) . . . . ?
C14 C13 C12 C11 -0.5(6) . . . . ?
C15 C13 C12 C11 -179.0(4) . . . . ?
C7 C8 C9 O4 179.5(3) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C7 C2 C1 O1 0.9(5) . . . . ?
C7 C2 C1 C6 -177.5(3) . . . . ?
C2 C3 C4 O2 173.7(3) . . . . ?
C2 C3 C4 C5 -5.3(5) . . . . ?
C6 C5 C14 C13 0.4(6) . . . . ?
C6 C11 C12 C13 -0.1(6) . . . . ?
C11 C6 C1 O1 -0.7(5) . . . . ?
C11 C6 C1 C2 177.7(3) . . . . ?
C1 C6 C11 O5 0.9(5) . . . . ?
C1 C6 C11 C12 -178.9(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
