# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ec68a
_audit_block_doi                 10.5517/ccxn0cx
_database_code_depnum_ccdc_archive 'CCDC 853379'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/ja4088677 2013
2 10.1002/anie.201108019 2012
_audit_update_record             
;
2011-11-09 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;
#TrackingRef 'Xray CIF_IMes+MMA.CIF'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H32 N2 O2'
_chemical_formula_sum            'C26 H32 N2 O2'
_chemical_formula_weight         404.54

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc '

loop_
_symmetry_equiv_pos_as_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                   40.091(5)
_cell_length_b                   7.8348(9)
_cell_length_c                   16.111(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.260(8)
_cell_angle_gamma                90.00
_cell_volume                     4649.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      28.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.658
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.146
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6830
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40348
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.36
_reflns_number_total             5797
_reflns_number_gt                4090
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0659P)²+1.6255P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5797
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09317(4) 0.73787(18) 0.59073(7) 0.0796(4) Uani 1 1 d . . .
O2 O 0.06963(3) 0.57474(16) 0.46762(7) 0.0643(3) Uani 1 1 d . . .
N1 N 0.12343(3) 0.55055(14) 0.32806(7) 0.0445(3) Uani 1 1 d . . .
N2 N 0.17442(3) 0.48007(15) 0.44036(7) 0.0470(3) Uani 1 1 d . . .
C1 C 0.14523(3) 0.59239(16) 0.41738(8) 0.0405(3) Uani 1 1 d . . .
C2 C 0.13949(4) 0.4170(2) 0.29926(10) 0.0548(4) Uani 1 1 d . . .
C3 C 0.17008(5) 0.3762(2) 0.36659(10) 0.0566(4) Uani 1 1 d . . .
C4 C 0.14073(4) 0.71323(17) 0.47206(9) 0.0446(3) Uani 1 1 d . . .
C5 C 0.10604(4) 0.80505(18) 0.45990(9) 0.0483(3) Uani 1 1 d . . .
C6 C 0.08921(4) 0.7078(2) 0.51411(9) 0.0532(4) Uani 1 1 d . . .
C7 C 0.11269(7) 0.9898(2) 0.49042(15) 0.0749(5) Uani 1 1 d . . .
C8 C 0.05473(7) 0.4632(4) 0.51521(18) 0.0920(7) Uani 1 1 d . . .
C9 C 0.09224(3) 0.64249(16) 0.26995(8) 0.0401(3) Uani 1 1 d . . .
C10 C 0.09618(4) 0.80769(18) 0.24270(8) 0.0445(3) Uani 1 1 d . . .
C11 C 0.06495(4) 0.8974(2) 0.19053(9) 0.0517(3) Uani 1 1 d . . .
C12 C 0.03076(4) 0.8266(2) 0.16532(9) 0.0549(4) Uani 1 1 d . . .
C13 C 0.02807(4) 0.6596(2) 0.18990(9) 0.0507(3) Uani 1 1 d . . .
C14 C 0.05826(4) 0.56448(17) 0.24195(8) 0.0443(3) Uani 1 1 d . . .
C15 C 0.13268(5) 0.8904(2) 0.27014(12) 0.0580(4) Uani 1 1 d . . .
C16 C -0.00306(6) 0.9293(4) 0.11414(18) 0.0857(6) Uani 1 1 d . . .
C17 C 0.05434(6) 0.3839(2) 0.26770(14) 0.0634(4) Uani 1 1 d . . .
C18 C 0.20295(3) 0.46134(16) 0.52780(8) 0.0412(3) Uani 1 1 d . . .
C19 C 0.23871(4) 0.49222(17) 0.53789(9) 0.0446(3) Uani 1 1 d . . .
C20 C 0.26622(4) 0.47022(18) 0.62298(10) 0.0474(3) Uani 1 1 d . . .
C21 C 0.25964(4) 0.41568(17) 0.69653(9) 0.0468(3) Uani 1 1 d . . .
C22 C 0.22400(4) 0.38503(18) 0.68387(9) 0.0469(3) Uani 1 1 d . . .
C23 C 0.19524(4) 0.40662(16) 0.60082(9) 0.0435(3) Uani 1 1 d . . .
C24 C 0.24787(6) 0.5444(3) 0.45947(12) 0.0631(4) Uani 1 1 d . . .
C25 C 0.29005(5) 0.3882(3) 0.78753(12) 0.0654(4) Uani 1 1 d . . .
C26 C 0.15724(4) 0.3687(2) 0.59217(13) 0.0594(4) Uani 1 1 d . . .
H2 H 0.1282(5) 0.377(2) 0.2397(12) 0.063(5) Uiso 1 1 d . . .
H3 H 0.1871(5) 0.294(2) 0.3717(12) 0.072(5) Uiso 1 1 d . . .
H4 H 0.1599(4) 0.7188(18) 0.5319(11) 0.052(4) Uiso 1 1 d . . .
H5 H 0.0884(4) 0.8049(17) 0.3980(10) 0.043(4) Uiso 1 1 d . . .
H7A H 0.1326(6) 0.998(3) 0.5550(15) 0.093(6) Uiso 1 1 d . . .
H7B H 0.0898(6) 1.043(3) 0.4882(13) 0.082(6) Uiso 1 1 d . . .
H7C H 0.1242(7) 1.054(3) 0.4540(16) 0.110(8) Uiso 1 1 d . . .
H8A H 0.0737(7) 0.419(3) 0.5670(17) 0.100(7) Uiso 1 1 d . . .
H8B H 0.0389(8) 0.386(4) 0.470(2) 0.134(11) Uiso 1 1 d . . .
H8C H 0.0396(8) 0.534(3) 0.5379(19) 0.128(10) Uiso 1 1 d . . .
H11 H 0.0680(4) 1.011(2) 0.1722(11) 0.066(5) Uiso 1 1 d . . .
H13 H 0.0048(5) 0.613(2) 0.1750(11) 0.062(5) Uiso 1 1 d . . .
H15A H 0.1414(5) 0.934(3) 0.3336(15) 0.087(6) Uiso 1 1 d . . .
H15B H 0.1521(6) 0.809(3) 0.2710(13) 0.087(6) Uiso 1 1 d . . .
H15C H 0.1329(6) 0.985(3) 0.2283(14) 0.091(6) Uiso 1 1 d . . .
H16A H 0.0023(6) 1.042(4) 0.1002(16) 0.106(8) Uiso 1 1 d . . .
H16B H -0.0157(8) 0.879(4) 0.055(2) 0.125(9) Uiso 1 1 d . . .
H16C H -0.0208(9) 0.935(4) 0.145(2) 0.155(12) Uiso 1 1 d . . .
H17A H 0.0623(7) 0.302(3) 0.2350(18) 0.119(8) Uiso 1 1 d . . .
H17B H 0.0689(7) 0.363(3) 0.3301(19) 0.115(8) Uiso 1 1 d . . .
H17C H 0.0292(8) 0.356(3) 0.2542(18) 0.128(9) Uiso 1 1 d . . .
H20 H 0.2910(5) 0.495(2) 0.6300(11) 0.066(5) Uiso 1 1 d . . .
H22 H 0.2185(4) 0.344(2) 0.7344(11) 0.055(4) Uiso 1 1 d . . .
H24A H 0.2489(6) 0.447(3) 0.4248(15) 0.093(7) Uiso 1 1 d . . .
H24B H 0.2719(6) 0.601(2) 0.4834(13) 0.078(6) Uiso 1 1 d . . .
H24C H 0.2296(6) 0.625(3) 0.4198(14) 0.083(6) Uiso 1 1 d . . .
H25A H 0.2931(7) 0.487(4) 0.8260(18) 0.122(9) Uiso 1 1 d . . .
H25B H 0.2846(7) 0.302(3) 0.8253(18) 0.118(8) Uiso 1 1 d . . .
H25C H 0.3120(8) 0.348(3) 0.7857(17) 0.122(9) Uiso 1 1 d . . .
H26A H 0.1408(6) 0.346(3) 0.5293(15) 0.083(6) Uiso 1 1 d . . .
H26B H 0.1588(5) 0.276(3) 0.6309(14) 0.084(6) Uiso 1 1 d . . .
H26C H 0.1480(6) 0.474(3) 0.6180(14) 0.099(7) Uiso 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2040(16) . ?
O2 C6 1.3415(19) . ?
O2 C8 1.439(2) . ?
N1 C1 1.3959(16) . ?
N1 C2 1.4002(17) . ?
N1 C9 1.4264(16) . ?
N2 C1 1.3926(16) . ?
N2 C3 1.3932(17) . ?
N2 C18 1.4289(16) . ?
C1 C4 1.3530(17) . ?
C2 C3 1.316(2) . ?
C4 C5 1.5081(19) . ?
C5 C6 1.505(2) . ?
C5 C7 1.518(2) . ?
C9 C14 1.3955(18) . ?
C9 C10 1.3956(19) . ?
C10 C11 1.392(2) . ?
C10 C15 1.499(2) . ?
C11 C12 1.383(2) . ?
C12 C13 1.384(2) . ?
C12 C16 1.511(2) . ?
C13 C14 1.386(2) . ?
C14 C17 1.500(2) . ?
C18 C23 1.3967(18) . ?
C18 C19 1.3983(19) . ?
C19 C20 1.3897(19) . ?
C19 C24 1.505(2) . ?
C20 C21 1.380(2) . ?
C21 C22 1.382(2) . ?
C21 C25 1.507(2) . ?
C22 C23 1.3892(19) . ?
C23 C26 1.504(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
C6 O2 C8 116.67(16) . . ?
C1 N1 C2 109.54(11) . . ?
C1 N1 C9 126.00(10) . . ?
C2 N1 C9 123.95(11) . . ?
C1 N2 C3 109.48(11) . . ?
C1 N2 C18 126.05(10) . . ?
C3 N2 C18 124.25(11) . . ?
C4 C1 N2 125.68(11) . . ?
C4 C1 N1 130.19(12) . . ?
N2 C1 N1 104.12(10) . . ?
C3 C2 N1 107.99(12) . . ?
C2 C3 N2 108.86(13) . . ?
C1 C4 C5 127.04(12) . . ?
C6 C5 C4 106.56(11) . . ?
C6 C5 C7 110.87(14) . . ?
C4 C5 C7 112.21(14) . . ?
O1 C6 O2 122.40(16) . . ?
O1 C6 C5 126.03(16) . . ?
O2 C6 C5 111.53(11) . . ?
C14 C9 C10 121.45(12) . . ?
C14 C9 N1 118.81(12) . . ?
C10 C9 N1 119.74(12) . . ?
C11 C10 C9 118.15(13) . . ?
C11 C10 C15 120.03(14) . . ?
C9 C10 C15 121.79(13) . . ?
C12 C11 C10 121.71(14) . . ?
C11 C12 C13 118.41(14) . . ?
C11 C12 C16 121.22(18) . . ?
C13 C12 C16 120.35(17) . . ?
C12 C13 C14 122.23(14) . . ?
C13 C14 C9 117.90(13) . . ?
C13 C14 C17 120.82(14) . . ?
C9 C14 C17 121.28(13) . . ?
C23 C18 C19 120.85(12) . . ?
C23 C18 N2 120.31(12) . . ?
C19 C18 N2 118.79(12) . . ?
C20 C19 C18 118.10(12) . . ?
C20 C19 C24 120.01(14) . . ?
C18 C19 C24 121.88(13) . . ?
C21 C20 C19 122.63(13) . . ?
C20 C21 C22 117.65(12) . . ?
C20 C21 C25 121.63(14) . . ?
C22 C21 C25 120.72(14) . . ?
C21 C22 C23 122.51(13) . . ?
C22 C23 C18 118.23(12) . . ?
C22 C23 C26 119.36(13) . . ?
C18 C23 C26 122.40(13) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.033


####################################################################### 
# 
# 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_p15156cu
_database_code_depnum_ccdc_archive 'CCDC 1061009'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;
_audit_creation_date             2015-03-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998),
 SHELXL-2014,
 and manual edit
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 O6'
_chemical_formula_sum            'C19 H24 O6'
_chemical_formula_weight         348.38
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2463(2)
_cell_length_b                   10.3683(3)
_cell_length_c                   19.3151(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1651.44(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9546
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.67
_cell_measurement_theta_min      4.58
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.875
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1009 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8788.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 2.00 0.0270
1.00 2.00 -2.00 0.0500
2.00 1.00 2.00 0.0400
2.00 1.00 0.00 0.0570
-1.00 1.00 7.00 0.0100
0.00 -1.00 -4.00 0.0440
-6.00 -5.00 -2.00 0.0720
-1.00 0.00 -7.00 0.0480
1.00 1.00 -7.00 0.0600
0.00 3.00 -7.00 0.0450
-2.00 7.00 -7.00 0.0350
3.00 -6.00 1.00 0.0550
0.00 -7.00 -3.00 0.0310
7.00 -6.00 -1.00 0.0640
-2.00 7.00 3.00 0.0300
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            40519
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         79.097
_diffrn_reflns_theta_min         4.578
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3433
_reflns_number_total             3557
_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_data_collection       'APEX2 2014.9-0 (Bruker-AXS, 2007)'
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_structure_solution    'XT-2014/4 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1422 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_abs_structure_Hooft   0.07(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.070
_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)+(0.0315P)²+0.3425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0619
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23254(14) 0.24829(11) 0.25005(6) 0.0192(2) Uani 1 1 d . . . . .
O2 O 0.33537(15) 0.14564(11) 0.34069(6) 0.0209(3) Uani 1 1 d . . . . .
O3 O 1.00576(16) 0.50516(12) 0.31547(7) 0.0248(3) Uani 1 1 d . . . . .
O4 O 0.42360(16) 0.11573(11) 0.13350(6) 0.0193(2) Uani 1 1 d . . . . .
H4 H 0.523(4) 0.090(3) 0.1322(13) 0.038(7) Uiso 1 1 d . . . . .
O5 O 0.67107(13) 0.18290(10) 0.24612(5) 0.0128(2) Uani 1 1 d . . . . .
O6 O 0.75229(14) 0.16546(12) 0.13315(6) 0.0180(2) Uani 1 1 d . . . . .
H6 H 0.836(3) 0.121(2) 0.1486(12) 0.034(6) Uiso 1 1 d . . . . .
C1 C 0.34786(19) 0.23022(15) 0.29832(8) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.48069(19) 0.33135(15) 0.29051(8) 0.0144(3) Uani 1 1 d . . . . .
H2 H 0.458(3) 0.395(2) 0.3257(11) 0.019(5) Uiso 1 1 d . . . . .
C3 C 0.65329(19) 0.27942(14) 0.29950(7) 0.0133(3) Uani 1 1 d . . . . .
C4 C 0.6836(2) 0.21649(15) 0.36942(8) 0.0158(3) Uani 1 1 d . . . . .
H4A H 0.625(3) 0.135(2) 0.3715(11) 0.024(5) Uiso 1 1 d . . . . .
H4B H 0.635(3) 0.271(2) 0.4045(11) 0.021(5) Uiso 1 1 d . . . . .
C5 C 0.8635(2) 0.19583(16) 0.38463(8) 0.0165(3) Uani 1 1 d . . . . .
H5 H 0.916(3) 0.148(2) 0.3459(10) 0.019(5) Uiso 1 1 d . . . . .
C6 C 0.9470(2) 0.32790(17) 0.38913(9) 0.0202(3) Uani 1 1 d . . . . .
H6A H 0.905(3) 0.376(2) 0.4292(13) 0.036(6) Uiso 1 1 d . . . . .
H6B H 1.062(3) 0.321(2) 0.3943(12) 0.028(6) Uiso 1 1 d . . . . .
C7 C 0.9172(2) 0.41371(16) 0.32757(8) 0.0168(3) Uani 1 1 d . . . . .
C8 C 0.7758(2) 0.38877(15) 0.27971(8) 0.0148(3) Uani 1 1 d . . . . .
H8 H 0.722(3) 0.475(2) 0.2755(11) 0.019(5) Uiso 1 1 d . . . . .
C9 C 0.83759(19) 0.34565(16) 0.20787(8) 0.0164(3) Uani 1 1 d . . . . .
H9A H 0.853(3) 0.415(2) 0.1771(11) 0.021(5) Uiso 1 1 d . . . . .
H9B H 0.935(3) 0.2960(19) 0.2130(10) 0.014(4) Uiso 1 1 d . . . . .
C10 C 0.70447(19) 0.25448(15) 0.18354(7) 0.0139(3) Uani 1 1 d . . . . .
C11 C 0.55282(19) 0.32674(15) 0.15786(8) 0.0140(3) Uani 1 1 d . . . . .
H11 H 0.591(3) 0.398(2) 0.1292(10) 0.017(5) Uiso 1 1 d . . . . .
C12 C 0.4321(2) 0.24883(15) 0.11226(8) 0.0161(3) Uani 1 1 d . . . . .
C13 C 0.2665(2) 0.30857(16) 0.12851(9) 0.0194(3) Uani 1 1 d . . . . .
H13A H 0.248(3) 0.384(2) 0.0972(11) 0.018(5) Uiso 1 1 d . . . . .
H13B H 0.174(3) 0.246(2) 0.1210(12) 0.033(6) Uiso 1 1 d . . . . .
C14 C 0.2738(2) 0.35427(16) 0.20304(9) 0.0181(3) Uani 1 1 d . . . . .
H14 H 0.197(3) 0.425(2) 0.2137(10) 0.016(5) Uiso 1 1 d . . . . .
C15 C 0.45172(19) 0.38751(14) 0.21820(8) 0.0146(3) Uani 1 1 d . . . . .
H15 H 0.467(3) 0.481(2) 0.2186(11) 0.022(5) Uiso 1 1 d . . . . .
C16 C 0.8961(2) 0.11948(16) 0.45052(8) 0.0190(3) Uani 1 1 d . . . . .
C17 C 1.0677(3) 0.07743(19) 0.46225(10) 0.0250(4) Uani 1 1 d . . . . .
H17A H 1.102(3) 0.017(3) 0.4263(14) 0.043(7) Uiso 1 1 d . . . . .
H17B H 1.081(3) 0.034(2) 0.5083(13) 0.037(7) Uiso 1 1 d . . . . .
H17C H 1.146(4) 0.150(3) 0.4620(14) 0.048(8) Uiso 1 1 d . . . . .
C18 C 0.7793(3) 0.0890(2) 0.49571(9) 0.0270(4) Uani 1 1 d . . . . .
H18A H 0.808(3) 0.039(3) 0.5363(14) 0.039(7) Uiso 1 1 d . . . . .
H18B H 0.665(3) 0.111(3) 0.4869(13) 0.037(7) Uiso 1 1 d . . . . .
C19 C 0.4717(2) 0.25661(18) 0.03518(9) 0.0218(3) Uani 1 1 d . . . . .
H19A H 0.579(3) 0.214(2) 0.0258(12) 0.032(6) Uiso 1 1 d . . . . .
H19B H 0.480(3) 0.345(2) 0.0190(12) 0.027(6) Uiso 1 1 d . . . . .
H19C H 0.383(3) 0.213(2) 0.0088(12) 0.029(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.345(2) . ?
O1 C14 1.466(2) . ?
O2 C1 1.204(2) . ?
O3 C7 1.220(2) . ?
O4 H4 0.86(3) . ?
O4 C12 1.4414(18) . ?
O5 C3 1.4443(17) . ?
O5 C10 1.4448(18) . ?
O6 H6 0.88(3) . ?
O6 C10 1.3982(18) . ?
C1 C2 1.524(2) . ?
C2 H2 0.97(2) . ?
C2 C3 1.532(2) . ?
C2 C15 1.532(2) . ?
C3 C4 1.520(2) . ?
C3 C8 1.566(2) . ?
C4 H4A 0.98(2) . ?
C4 H4B 0.97(2) . ?
C4 C5 1.528(2) . ?
C5 H5 1.00(2) . ?
C5 C6 1.535(2) . ?
C5 C16 1.523(2) . ?
C6 H6A 0.99(3) . ?
C6 H6B 0.96(3) . ?
C6 C7 1.505(2) . ?
C7 C8 1.510(2) . ?
C8 H8 1.01(2) . ?
C8 C9 1.544(2) . ?
C9 H9A 0.94(2) . ?
C9 H9B 0.96(2) . ?
C9 C10 1.523(2) . ?
C10 C11 1.540(2) . ?
C11 H11 0.97(2) . ?
C11 C12 1.556(2) . ?
C11 C15 1.565(2) . ?
C12 C13 1.531(2) . ?
C12 C19 1.526(2) . ?
C13 H13A 1.00(2) . ?
C13 H13B 1.01(3) . ?
C13 C14 1.517(2) . ?
C14 H14 0.99(2) . ?
C14 C15 1.535(2) . ?
C15 H15 0.98(2) . ?
C16 C17 1.497(3) . ?
C16 C18 1.338(3) . ?
C17 H17A 0.98(3) . ?
C17 H17B 1.00(3) . ?
C17 H17C 0.99(3) . ?
C18 H18A 0.97(3) . ?
C18 H18B 0.99(3) . ?
C19 H19A 1.00(3) . ?
C19 H19B 0.97(2) . ?
C19 H19C 1.00(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C14 111.70(12) . . ?
C12 O4 H4 103.7(18) . . ?
C3 O5 C10 105.11(11) . . ?
C10 O6 H6 109.4(16) . . ?
O1 C1 C2 110.10(13) . . ?
O2 C1 O1 120.81(14) . . ?
O2 C1 C2 129.06(15) . . ?
C1 C2 H2 105.4(13) . . ?
C1 C2 C3 114.51(12) . . ?
C1 C2 C15 103.87(13) . . ?
C3 C2 H2 109.7(13) . . ?
C3 C2 C15 112.45(12) . . ?
C15 C2 H2 110.5(12) . . ?
O5 C3 C2 104.89(12) . . ?
O5 C3 C4 108.66(12) . . ?
O5 C3 C8 105.18(11) . . ?
C2 C3 C8 108.50(12) . . ?
C4 C3 C2 113.85(13) . . ?
C4 C3 C8 114.93(13) . . ?
C3 C4 H4A 109.1(13) . . ?
C3 C4 H4B 107.6(13) . . ?
C3 C4 C5 112.99(13) . . ?
H4A C4 H4B 105.8(18) . . ?
C5 C4 H4A 110.7(13) . . ?
C5 C4 H4B 110.3(13) . . ?
C4 C5 H5 110.4(12) . . ?
C4 C5 C6 108.74(13) . . ?
C6 C5 H5 107.1(12) . . ?
C16 C5 C4 113.91(13) . . ?
C16 C5 H5 106.8(12) . . ?
C16 C5 C6 109.71(13) . . ?
C5 C6 H6A 110.0(15) . . ?
C5 C6 H6B 112.6(14) . . ?
H6A C6 H6B 108(2) . . ?
C7 C6 C5 114.17(13) . . ?
C7 C6 H6A 105.2(14) . . ?
C7 C6 H6B 106.8(14) . . ?
O3 C7 C6 120.88(15) . . ?
O3 C7 C8 118.57(15) . . ?
C6 C7 C8 120.55(14) . . ?
C3 C8 H8 112.3(13) . . ?
C7 C8 C3 118.21(13) . . ?
C7 C8 H8 103.8(12) . . ?
C7 C8 C9 110.18(13) . . ?
C9 C8 C3 102.86(12) . . ?
C9 C8 H8 109.4(12) . . ?
C8 C9 H9A 113.1(13) . . ?
C8 C9 H9B 109.8(12) . . ?
H9A C9 H9B 111.1(18) . . ?
C10 C9 C8 102.66(12) . . ?
C10 C9 H9A 112.2(13) . . ?
C10 C9 H9B 107.6(12) . . ?
O5 C10 C9 101.42(11) . . ?
O5 C10 C11 111.38(12) . . ?
O6 C10 O5 107.28(12) . . ?
O6 C10 C9 114.91(13) . . ?
O6 C10 C11 109.02(12) . . ?
C9 C10 C11 112.51(13) . . ?
C10 C11 H11 106.9(12) . . ?
C10 C11 C12 116.72(13) . . ?
C10 C11 C15 112.86(12) . . ?
C12 C11 H11 106.0(12) . . ?
C12 C11 C15 106.84(12) . . ?
C15 C11 H11 106.9(12) . . ?
O4 C12 C11 111.53(12) . . ?
O4 C12 C13 106.61(13) . . ?
O4 C12 C19 109.78(13) . . ?
C13 C12 C11 104.15(12) . . ?
C19 C12 C11 112.81(13) . . ?
C19 C12 C13 111.68(14) . . ?
C12 C13 H13A 109.2(12) . . ?
C12 C13 H13B 112.6(14) . . ?
H13A C13 H13B 107.3(18) . . ?
C14 C13 C12 106.59(13) . . ?
C14 C13 H13A 109.6(12) . . ?
C14 C13 H13B 111.5(14) . . ?
O1 C14 C13 110.16(13) . . ?
O1 C14 H14 106.1(12) . . ?
O1 C14 C15 105.79(13) . . ?
C13 C14 H14 113.8(12) . . ?
C13 C14 C15 106.81(13) . . ?
C15 C14 H14 113.8(12) . . ?
C2 C15 C11 116.28(12) . . ?
C2 C15 C14 103.75(13) . . ?
C2 C15 H15 110.5(13) . . ?
C11 C15 H15 109.8(13) . . ?
C14 C15 C11 106.05(13) . . ?
C14 C15 H15 110.1(13) . . ?
C17 C16 C5 116.41(14) . . ?
C18 C16 C5 122.73(16) . . ?
C18 C16 C17 120.85(16) . . ?
C16 C17 H17A 110.5(17) . . ?
C16 C17 H17B 111.6(16) . . ?
C16 C17 H17C 113.0(17) . . ?
H17A C17 H17B 108(2) . . ?
H17A C17 H17C 107(2) . . ?
H17B C17 H17C 106(2) . . ?
C16 C18 H18A 118.5(17) . . ?
C16 C18 H18B 121.4(15) . . ?
H18A C18 H18B 120(2) . . ?
C12 C19 H19A 110.0(13) . . ?
C12 C19 H19B 112.3(13) . . ?
C12 C19 H19C 108.5(14) . . ?
H19A C19 H19B 107(2) . . ?
H19A C19 H19C 110.7(19) . . ?
H19B C19 H19C 108(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O6 0.86(3) 2.04(3) 2.7591(18) 140(2) .
O6 H6 O3 0.88(3) 1.90(3) 2.7799(17) 172(2) 3_745
C2 H2 O4 0.97(2) 2.61(2) 3.3870(19) 138.0(16) 3_655
C4 H4A O2 0.98(2) 2.46(2) 3.015(2) 115.7(16) .
C8 H8 O4 1.01(2) 2.58(2) 3.324(2) 130.9(15) 3_655
C9 H9B O1 0.96(2) 2.60(2) 3.506(2) 156.9(16) 1_655
C15 H15 O2 0.98(2) 2.62(2) 3.397(2) 136.0(17) 3_655
C15 H15 O5 0.98(2) 2.48(2) 3.2986(18) 141.5(17) 3_655
C19 H19A O6 1.00(3) 2.57(2) 3.135(2) 115.5(16) .

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
O1 C1 C2 C3 -138.72(13) . . . . ?
O1 C1 C2 C15 -15.70(16) . . . . ?
O1 C14 C15 C2 -20.00(15) . . . . ?
O1 C14 C15 C11 103.00(14) . . . . ?
O2 C1 C2 C3 43.2(2) . . . . ?
O2 C1 C2 C15 166.23(16) . . . . ?
O3 C7 C8 C3 -174.28(15) . . . . ?
O3 C7 C8 C9 67.94(19) . . . . ?
O4 C12 C13 C14 86.84(15) . . . . ?
O5 C3 C4 C5 77.86(15) . . . . ?
O5 C3 C8 C7 -114.56(14) . . . . ?
O5 C3 C8 C9 7.03(15) . . . . ?
O5 C10 C11 C12 -84.55(15) . . . . ?
O5 C10 C11 C15 39.79(17) . . . . ?
O6 C10 C11 C12 33.65(18) . . . . ?
O6 C10 C11 C15 157.99(12) . . . . ?
C1 O1 C14 C13 126.20(14) . . . . ?
C1 O1 C14 C15 11.11(16) . . . . ?
C1 C2 C3 O5 60.00(15) . . . . ?
C1 C2 C3 C4 -58.66(17) . . . . ?
C1 C2 C3 C8 172.01(12) . . . . ?
C1 C2 C15 C11 -94.84(15) . . . . ?
C1 C2 C15 C14 21.15(15) . . . . ?
C2 C3 C4 C5 -165.66(13) . . . . ?
C2 C3 C8 C7 133.63(14) . . . . ?
C2 C3 C8 C9 -104.78(13) . . . . ?
C3 O5 C10 O6 169.22(12) . . . . ?
C3 O5 C10 C9 48.36(14) . . . . ?
C3 O5 C10 C11 -71.54(14) . . . . ?
C3 C2 C15 C11 29.52(18) . . . . ?
C3 C2 C15 C14 145.52(12) . . . . ?
C3 C4 C5 C6 63.83(16) . . . . ?
C3 C4 C5 C16 -173.48(13) . . . . ?
C3 C8 C9 C10 21.03(15) . . . . ?
C4 C3 C8 C7 4.9(2) . . . . ?
C4 C3 C8 C9 126.49(13) . . . . ?
C4 C5 C6 C7 -52.59(18) . . . . ?
C4 C5 C16 C17 170.32(14) . . . . ?
C4 C5 C16 C18 -8.8(2) . . . . ?
C5 C6 C7 O3 -161.18(16) . . . . ?
C5 C6 C7 C8 19.3(2) . . . . ?
C6 C5 C16 C17 -67.52(19) . . . . ?
C6 C5 C16 C18 113.37(19) . . . . ?
C6 C7 C8 C3 5.3(2) . . . . ?
C6 C7 C8 C9 -112.51(17) . . . . ?
C7 C8 C9 C10 147.92(13) . . . . ?
C8 C3 C4 C5 -39.64(18) . . . . ?
C8 C9 C10 O5 -42.13(14) . . . . ?
C8 C9 C10 O6 -157.47(12) . . . . ?
C8 C9 C10 C11 76.97(15) . . . . ?
C9 C10 C11 C12 162.34(13) . . . . ?
C9 C10 C11 C15 -73.31(16) . . . . ?
C10 O5 C3 C2 79.80(13) . . . . ?
C10 O5 C3 C4 -158.10(12) . . . . ?
C10 O5 C3 C8 -34.56(14) . . . . ?
C10 C11 C12 O4 34.69(18) . . . . ?
C10 C11 C12 C13 149.29(13) . . . . ?
C10 C11 C12 C19 -89.42(16) . . . . ?
C10 C11 C15 C2 -19.82(19) . . . . ?
C10 C11 C15 C14 -134.52(14) . . . . ?
C11 C12 C13 C14 -31.21(16) . . . . ?
C12 C11 C15 C2 109.78(14) . . . . ?
C12 C11 C15 C14 -4.92(15) . . . . ?
C12 C13 C14 O1 -85.69(15) . . . . ?
C12 C13 C14 C15 28.74(16) . . . . ?
C13 C14 C15 C2 -137.36(13) . . . . ?
C13 C14 C15 C11 -14.36(16) . . . . ?
C14 O1 C1 O2 -178.78(14) . . . . ?
C14 O1 C1 C2 2.96(17) . . . . ?
C15 C2 C3 O5 -58.27(15) . . . . ?
C15 C2 C3 C4 -176.92(12) . . . . ?
C15 C2 C3 C8 53.75(16) . . . . ?
C15 C11 C12 O4 -92.67(15) . . . . ?
C15 C11 C12 C13 21.93(15) . . . . ?
C15 C11 C12 C19 143.23(13) . . . . ?
C16 C5 C6 C7 -177.78(14) . . . . ?
C19 C12 C13 C14 -153.25(14) . . . . ?

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

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF, Heptane, Benzene'
####################################################################### 
# 
# 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_rac01
_database_code_depnum_ccdc_archive 'CCDC 1061010'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 O4'
_chemical_formula_weight         314.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   11.7563(19)
_cell_length_b                   5.3917(8)
_cell_length_c                   12.861(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.529(8)
_cell_angle_gamma                90
_cell_volume                     789.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1925
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      21.03

_exptl_crystal_description       hollow
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   0.5501
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS-2014/4 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            8970
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.636
_diffrn_reflns_theta_max         22.464
_diffrn_reflns_theta_full        22.464
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2037
_reflns_number_gt                1451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'APEX2 v2014.9-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0594P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 511 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2037
_refine_ls_number_parameters     213
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1037
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3461(4) 0.5365(8) 0.3878(3) 0.0396(12) Uani 1 1 d . . . . .
C1 C 0.4556(7) 0.4881(12) 0.3816(5) 0.0356(19) Uani 1 1 d . . . . .
O2 O 0.5025(4) 0.2972(8) 0.4167(3) 0.0490(14) Uani 1 1 d . . . . .
C2 C 0.5051(5) 0.7063(10) 0.3307(5) 0.0293(16) Uani 1 1 d . . . . .
H2 H 0.5428 0.8178 0.3918 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6016(6) 0.6448(10) 0.2746(5) 0.0290(17) Uani 1 1 d . . . . .
C4 C 0.7038(6) 0.5073(14) 0.3464(5) 0.0465(19) Uani 1 1 d . . . . .
H4A H 0.6736 0.3951 0.3943 0.056 Uiso 1 1 calc R U . . .
H4B H 0.7570 0.6285 0.3921 0.056 Uiso 1 1 calc R U . . .
C5 C 0.7733(5) 0.3556(10) 0.2834(5) 0.0281(16) Uani 1 1 d . . . . .
H5 H 0.7183 0.2320 0.2392 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8739(6) 0.2141(10) 0.3541(5) 0.0316(16) Uani 1 1 d . . . . .
C17 C 0.8632(7) 0.1281(13) 0.4544(6) 0.056(2) Uani 1 1 d . . . . .
H17A H 0.9335 0.0334 0.4894 0.084 Uiso 1 1 calc R U . . .
H17B H 0.7938 0.0212 0.4441 0.084 Uiso 1 1 calc R U . . .
H17C H 0.8547 0.2697 0.4996 0.084 Uiso 1 1 calc R U . . .
C18 C 0.9737(6) 0.1587(14) 0.3197(6) 0.062(2) Uani 1 1 d . . . . .
H18A H 1.0348 0.0627 0.3639 0.074 Uiso 1 1 calc R U . . .
H18B H 0.9810 0.2168 0.2519 0.074 Uiso 1 1 calc R U . . .
C6 C 0.8111(6) 0.5325(13) 0.2068(6) 0.0442(18) Uani 1 1 d . . . . .
H6A H 0.8703 0.6486 0.2489 0.053 Uiso 1 1 calc R U . . .
H6B H 0.8493 0.4362 0.1594 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7114(6) 0.6803(11) 0.1381(5) 0.0317(17) Uani 1 1 d . . . . .
O3 O 0.7222(4) 0.7704(8) 0.0541(4) 0.0436(12) Uani 1 1 d . . . . .
C8 C 0.6042(5) 0.7252(10) 0.1764(5) 0.0270(15) Uani 1 1 d . . . . .
C9 C 0.5096(5) 0.8726(11) 0.0995(5) 0.0315(16) Uani 1 1 d . . . . .
H9A H 0.5094 1.0436 0.1275 0.038 Uiso 1 1 calc R U . . .
H9B H 0.5297 0.8828 0.0294 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3886(5) 0.7674(10) 0.0819(5) 0.0305(15) Uani 1 1 d . . . . .
H10 H 0.3484 0.7139 0.0119 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3363(5) 0.7471(10) 0.1604(5) 0.0256(15) Uani 1 1 d . . . . .
C12 C 0.2148(6) 0.6428(10) 0.1542(5) 0.0325(17) Uani 1 1 d . . . . .
O4 O 0.2230(4) 0.3726(8) 0.1651(3) 0.0360(12) Uani 1 1 d D . . . .
H4O H 0.245(6) 0.322(13) 0.112(4) 0.054 Uiso 1 1 d D U . . .
C19 C 0.1219(5) 0.7101(11) 0.0538(5) 0.0397(18) Uani 1 1 d . . . . .
H19A H 0.1426 0.6385 -0.0090 0.060 Uiso 1 1 calc R U . . .
H19B H 0.1170 0.8910 0.0465 0.060 Uiso 1 1 calc R U . . .
H19C H 0.0457 0.6445 0.0589 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1888(6) 0.7406(13) 0.2568(5) 0.0410(17) Uani 1 1 d . . . . .
H13A H 0.1460 0.9002 0.2429 0.049 Uiso 1 1 calc R U . . .
H13B H 0.1398 0.6206 0.2846 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3051(6) 0.7757(11) 0.3367(5) 0.0351(17) Uani 1 1 d . . . . .
H14 H 0.3016 0.9069 0.3907 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3927(5) 0.8399(10) 0.2713(5) 0.0271(16) Uani 1 1 d . . . . .
H15 H 0.4056 1.0232 0.2706 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.336(8) . ?
O1 C14 1.473(7) . ?
C1 O2 1.201(8) . ?
C1 C2 1.530(8) . ?
C2 C3 1.526(8) . ?
C2 C15 1.531(8) . ?
C2 H2 1.0000 . ?
C3 C8 1.342(8) . ?
C3 C4 1.513(9) . ?
C4 C5 1.525(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C16 1.506(8) . ?
C5 C6 1.516(8) . ?
C5 H5 1.0000 . ?
C16 C18 1.387(8) . ?
C16 C17 1.406(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C6 C7 1.506(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.221(7) . ?
C7 C8 1.484(8) . ?
C8 C9 1.515(8) . ?
C9 C10 1.495(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.311(7) . ?
C10 H10 0.9500 . ?
C11 C15 1.499(8) . ?
C11 C12 1.519(8) . ?
C12 O4 1.465(7) . ?
C12 C19 1.512(8) . ?
C12 C13 1.522(8) . ?
O4 H4O 0.83(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13 C14 1.502(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.524(8) . ?
C14 H14 1.0000 . ?
C15 H15 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 O1 C14 110.9(5) . . ?
O2 C1 O1 120.2(6) . . ?
O2 C1 C2 129.2(7) . . ?
O1 C1 C2 110.5(6) . . ?
C3 C2 C1 116.3(5) . . ?
C3 C2 C15 121.1(5) . . ?
C1 C2 C15 101.7(5) . . ?
C3 C2 H2 105.5 . . ?
C1 C2 H2 105.5 . . ?
C15 C2 H2 105.5 . . ?
C8 C3 C4 122.1(6) . . ?
C8 C3 C2 124.7(5) . . ?
C4 C3 C2 112.8(5) . . ?
C3 C4 C5 112.8(5) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C16 C5 C6 113.4(5) . . ?
C16 C5 C4 113.3(5) . . ?
C6 C5 C4 107.0(5) . . ?
C16 C5 H5 107.6 . . ?
C6 C5 H5 107.6 . . ?
C4 C5 H5 107.6 . . ?
C18 C16 C17 120.0(6) . . ?
C18 C16 C5 121.1(6) . . ?
C17 C16 C5 118.9(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 120.0 . . ?
C16 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C7 C6 C5 113.7(5) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O3 C7 C8 120.9(6) . . ?
O3 C7 C6 119.5(6) . . ?
C8 C7 C6 119.5(6) . . ?
C3 C8 C7 118.7(5) . . ?
C3 C8 C9 126.7(5) . . ?
C7 C8 C9 114.5(5) . . ?
C10 C9 C8 114.5(5) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 121.8(6) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C15 121.6(5) . . ?
C10 C11 C12 127.4(5) . . ?
C15 C11 C12 111.0(5) . . ?
O4 C12 C19 109.7(5) . . ?
O4 C12 C11 109.0(5) . . ?
C19 C12 C11 115.1(5) . . ?
O4 C12 C13 106.5(5) . . ?
C19 C12 C13 113.5(5) . . ?
C11 C12 C13 102.6(5) . . ?
C12 O4 H4O 106(5) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C13 C12 106.9(5) . . ?
C14 C13 H13A 110.4 . . ?
C12 C13 H13A 110.4 . . ?
C14 C13 H13B 110.4 . . ?
C12 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
O1 C14 C13 109.5(5) . . ?
O1 C14 C15 104.8(5) . . ?
C13 C14 C15 106.0(5) . . ?
O1 C14 H14 112.0 . . ?
C13 C14 H14 112.0 . . ?
C15 C14 H14 112.0 . . ?
C11 C15 C14 104.5(5) . . ?
C11 C15 C2 116.0(5) . . ?
C14 C15 C2 103.6(5) . . ?
C11 C15 H15 110.8 . . ?
C14 C15 H15 110.8 . . ?
C2 C15 H15 110.8 . . ?

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
C14 O1 C1 O2 -178.0(5) . . . . ?
C14 O1 C1 C2 4.1(6) . . . . ?
O2 C1 C2 C3 28.0(9) . . . . ?
O1 C1 C2 C3 -154.4(5) . . . . ?
O2 C1 C2 C15 161.6(6) . . . . ?
O1 C1 C2 C15 -20.8(6) . . . . ?
C1 C2 C3 C8 132.6(6) . . . . ?
C15 C2 C3 C8 8.5(8) . . . . ?
C1 C2 C3 C4 -54.4(7) . . . . ?
C15 C2 C3 C4 -178.6(5) . . . . ?
C8 C3 C4 C5 -30.4(9) . . . . ?
C2 C3 C4 C5 156.4(5) . . . . ?
C3 C4 C5 C16 -178.9(5) . . . . ?
C3 C4 C5 C6 55.4(7) . . . . ?
C6 C5 C16 C18 -29.2(8) . . . . ?
C4 C5 C16 C18 -151.3(6) . . . . ?
C6 C5 C16 C17 153.7(6) . . . . ?
C4 C5 C16 C17 31.6(8) . . . . ?
C16 C5 C6 C7 -178.3(5) . . . . ?
C4 C5 C6 C7 -52.7(7) . . . . ?
C5 C6 C7 O3 -158.3(6) . . . . ?
C5 C6 C7 C8 24.8(8) . . . . ?
C4 C3 C8 C7 -0.8(8) . . . . ?
C2 C3 C8 C7 171.5(5) . . . . ?
C4 C3 C8 C9 -177.5(6) . . . . ?
C2 C3 C8 C9 -5.2(9) . . . . ?
O3 C7 C8 C3 -172.9(5) . . . . ?
C6 C7 C8 C3 3.9(8) . . . . ?
O3 C7 C8 C9 4.1(8) . . . . ?
C6 C7 C8 C9 -179.1(5) . . . . ?
C3 C8 C9 C10 -49.6(8) . . . . ?
C7 C8 C9 C10 133.6(5) . . . . ?
C8 C9 C10 C11 62.6(8) . . . . ?
C9 C10 C11 C15 3.1(9) . . . . ?
C9 C10 C11 C12 -179.5(5) . . . . ?
C10 C11 C12 O4 84.5(7) . . . . ?
C15 C11 C12 O4 -98.0(5) . . . . ?
C10 C11 C12 C19 -39.2(8) . . . . ?
C15 C11 C12 C19 138.4(5) . . . . ?
C10 C11 C12 C13 -162.9(6) . . . . ?
C15 C11 C12 C13 14.7(6) . . . . ?
O4 C12 C13 C14 86.9(6) . . . . ?
C19 C12 C13 C14 -152.3(5) . . . . ?
C11 C12 C13 C14 -27.5(6) . . . . ?
C1 O1 C14 C13 127.9(5) . . . . ?
C1 O1 C14 C15 14.6(6) . . . . ?
C12 C13 C14 O1 -81.9(6) . . . . ?
C12 C13 C14 C15 30.7(6) . . . . ?
C10 C11 C15 C14 -178.9(5) . . . . ?
C12 C11 C15 C14 3.4(6) . . . . ?
C10 C11 C15 C2 -65.5(7) . . . . ?
C12 C11 C15 C2 116.8(5) . . . . ?
O1 C14 C15 C11 95.2(5) . . . . ?
C13 C14 C15 C11 -20.6(6) . . . . ?
O1 C14 C15 C2 -26.7(5) . . . . ?
C13 C14 C15 C2 -142.5(5) . . . . ?
C3 C2 C15 C11 44.8(7) . . . . ?
C1 C2 C15 C11 -85.9(6) . . . . ?
C3 C2 C15 C14 158.7(5) . . . . ?
C1 C2 C15 C14 28.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 1.00 2.65 3.309(7) 123.5 2_656
O4 H4O O3 0.83(3) 2.28(3) 3.094(6) 165(7) 2_645
C15 H15 O2 1.00 2.44 3.167(7) 129.5 1_565

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pentane, Diethyl Ether'
####################################################################### 
# 
# 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_rac03
_database_code_depnum_ccdc_archive 'CCDC 1061011'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 O5'
_chemical_formula_weight         330.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   6.9222(2)
_cell_length_b                   11.1470(4)
_cell_length_c                   10.4409(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.070(2)
_cell_angle_gamma                90
_cell_volume                     803.61(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9893
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      35.53

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6239
_exptl_absorpt_correction_T_max  0.7475
_exptl_absorpt_process_details   'SADABS-2014/4 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            30117
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.955
_diffrn_reflns_theta_max         36.317
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7796
_reflns_number_gt                6951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'APEX2 v2014.9-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.0123P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3016 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.5(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7796
_refine_ls_number_parameters     222
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1198
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67803(17) 0.35258(11) 0.25289(11) 0.0167(2) Uani 1 1 d . . . . .
C1 C 0.63608(19) 0.36312(13) 0.37701(14) 0.0128(2) Uani 1 1 d . . . . .
O2 O 0.62003(17) 0.27608(10) 0.44317(12) 0.0177(2) Uani 1 1 d . . . . .
C2 C 0.60857(18) 0.49575(12) 0.40836(12) 0.0109(2) Uani 1 1 d . . . . .
H2 H 0.4698 0.5133 0.3818 0.013 Uiso 1 1 calc R U . . .
C3 C 0.63235(19) 0.52687(12) 0.54905(13) 0.0108(2) Uani 1 1 d . . . . .
C4 C 0.4753(2) 0.46995(14) 0.62204(13) 0.0139(2) Uani 1 1 d . . . . .
H4A H 0.4519 0.3874 0.5897 0.017 Uiso 1 1 calc R U . . .
H4B H 0.3539 0.5160 0.6051 0.017 Uiso 1 1 calc R U . . .
C5 C 0.5248(2) 0.46501(13) 0.76660(13) 0.0125(2) Uani 1 1 d . . . . .
H5 H 0.6428 0.4140 0.7829 0.015 Uiso 1 1 calc R U . . .
C16 C 0.3659(2) 0.41396(13) 0.84208(14) 0.0147(2) Uani 1 1 d . . . . .
C17 C 0.1649(2) 0.46431(18) 0.81558(18) 0.0227(3) Uani 1 1 d . . . . .
H17A H 0.0792 0.4315 0.8777 0.034 Uiso 1 1 calc R U . . .
H17B H 0.1155 0.4422 0.7285 0.034 Uiso 1 1 calc R U . . .
H17C H 0.1692 0.5519 0.8233 0.034 Uiso 1 1 calc R U . . .
C18 C 0.4057(3) 0.33089(15) 0.93223(16) 0.0207(3) Uani 1 1 d . . . . .
H18A H 0.3058 0.3018 0.9819 0.025 Uiso 1 1 calc R U . . .
H18B H 0.5338 0.3009 0.9467 0.025 Uiso 1 1 calc R U . . .
C6 C 0.5752(2) 0.59233(13) 0.80974(13) 0.0140(2) Uani 1 1 d . . . . .
H6A H 0.4587 0.6435 0.7960 0.017 Uiso 1 1 calc R U . . .
H6B H 0.6141 0.5920 0.9028 0.017 Uiso 1 1 calc R U . . .
C7 C 0.7361(2) 0.64501(13) 0.73849(14) 0.0140(2) Uani 1 1 d . . . . .
O3 O 0.83953(19) 0.72382(12) 0.78984(12) 0.0216(2) Uani 1 1 d . . . . .
C8 C 0.76292(19) 0.60475(12) 0.60530(13) 0.0118(2) Uani 1 1 d . . . . .
C9 C 0.9282(2) 0.66814(14) 0.54670(15) 0.0157(2) Uani 1 1 d . . . . .
H9A H 0.8762 0.7428 0.5061 0.019 Uiso 1 1 calc R U . . .
H9B H 1.0228 0.6922 0.6176 0.019 Uiso 1 1 calc R U . . .
C10 C 1.0375(2) 0.60223(13) 0.44845(14) 0.0133(2) Uani 1 1 d . . . . .
H10 H 1.1720 0.6319 0.4387 0.016 Uiso 1 1 calc R U . . .
O5 O 1.01273(14) 0.47271(10) 0.43656(10) 0.01305(18) Uani 1 1 d . . . . .
C11 C 0.94111(19) 0.55097(12) 0.33345(13) 0.0112(2) Uani 1 1 d . . . . .
C12 C 1.0337(2) 0.53809(13) 0.20457(13) 0.0134(2) Uani 1 1 d . . . . .
O4 O 1.21209(15) 0.47544(12) 0.21641(12) 0.0175(2) Uani 1 1 d D . . . .
H4O H 1.189(4) 0.405(2) 0.235(3) 0.026 Uiso 1 1 d D U . . .
C19 C 1.0782(3) 0.66152(17) 0.15206(19) 0.0248(3) Uani 1 1 d . . . . .
H19A H 1.1784 0.7003 0.2089 0.037 Uiso 1 1 calc R U . . .
H19B H 0.9605 0.7106 0.1475 0.037 Uiso 1 1 calc R U . . .
H19C H 1.1245 0.6532 0.0660 0.037 Uiso 1 1 calc R U . . .
C13 C 0.8747(2) 0.47240(17) 0.11840(14) 0.0175(3) Uani 1 1 d . . . . .
H13A H 0.8498 0.5155 0.0360 0.021 Uiso 1 1 calc R U . . .
H13B H 0.9165 0.3896 0.0999 0.021 Uiso 1 1 calc R U . . .
C14 C 0.69167(19) 0.47010(15) 0.19210(13) 0.0145(2) Uani 1 1 d . . . . .
H14 H 0.5727 0.4906 0.1364 0.017 Uiso 1 1 calc R U . . .
C15 C 0.72406(19) 0.55554(13) 0.30684(13) 0.0118(2) Uani 1 1 d . . . . .
H15 H 0.6769 0.6385 0.2859 0.014 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3531(18) . ?
O1 C14 1.462(2) . ?
C1 O2 1.2007(19) . ?
C1 C2 1.5291(19) . ?
C2 C3 1.5070(18) . ?
C2 C15 1.5255(19) . ?
C2 H2 1.0000 . ?
C3 C8 1.3565(18) . ?
C3 C4 1.5109(19) . ?
C4 C5 1.5248(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C16 1.509(2) . ?
C5 C6 1.522(2) . ?
C5 H5 1.0000 . ?
C16 C18 1.335(2) . ?
C16 C17 1.508(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C6 C7 1.502(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.2318(18) . ?
C7 C8 1.485(2) . ?
C8 C9 1.511(2) . ?
C9 C10 1.508(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.4490(19) . ?
C10 O5 1.4582(18) . ?
C10 H10 1.0000 . ?
O5 C11 1.4458(17) . ?
C11 C15 1.5093(19) . ?
C11 C12 1.5377(19) . ?
C12 O4 1.4163(18) . ?
C12 C19 1.521(2) . ?
C12 C13 1.555(2) . ?
O4 H4O 0.83(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13 C14 1.528(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.534(2) . ?
C14 H14 1.0000 . ?
C15 H15 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 O1 C14 111.28(11) . . ?
O2 C1 O1 121.05(13) . . ?
O2 C1 C2 129.80(13) . . ?
O1 C1 C2 109.11(12) . . ?
C3 C2 C15 123.39(12) . . ?
C3 C2 C1 115.12(11) . . ?
C15 C2 C1 101.21(11) . . ?
C3 C2 H2 105.2 . . ?
C15 C2 H2 105.2 . . ?
C1 C2 H2 105.2 . . ?
C8 C3 C2 126.34(12) . . ?
C8 C3 C4 122.11(12) . . ?
C2 C3 C4 111.24(11) . . ?
C3 C4 C5 113.28(11) . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C16 C5 C6 110.93(12) . . ?
C16 C5 C4 114.17(11) . . ?
C6 C5 C4 106.86(11) . . ?
C16 C5 H5 108.2 . . ?
C6 C5 H5 108.2 . . ?
C4 C5 H5 108.2 . . ?
C18 C16 C17 121.95(15) . . ?
C18 C16 C5 120.53(14) . . ?
C17 C16 C5 117.47(13) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 120.0 . . ?
C16 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C7 C6 C5 112.36(12) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O3 C7 C8 121.04(14) . . ?
O3 C7 C6 119.45(13) . . ?
C8 C7 C6 119.46(12) . . ?
C3 C8 C7 118.36(12) . . ?
C3 C8 C9 128.65(13) . . ?
C7 C8 C9 112.73(12) . . ?
C10 C9 C8 118.59(12) . . ?
C10 C9 H9A 107.7 . . ?
C8 C9 H9A 107.7 . . ?
C10 C9 H9B 107.7 . . ?
C8 C9 H9B 107.7 . . ?
H9A C9 H9B 107.1 . . ?
C11 C10 O5 59.64(9) . . ?
C11 C10 C9 122.14(12) . . ?
O5 C10 C9 118.60(12) . . ?
C11 C10 H10 115.1 . . ?
O5 C10 H10 115.1 . . ?
C9 C10 H10 115.1 . . ?
C11 O5 C10 59.86(9) . . ?
O5 C11 C10 60.50(9) . . ?
O5 C11 C15 116.21(11) . . ?
C10 C11 C15 122.21(12) . . ?
O5 C11 C12 116.94(11) . . ?
C10 C11 C12 124.47(12) . . ?
C15 C11 C12 108.27(11) . . ?
O4 C12 C19 106.25(13) . . ?
O4 C12 C11 112.63(11) . . ?
C19 C12 C11 109.80(13) . . ?
O4 C12 C13 113.30(13) . . ?
C19 C12 C13 111.77(13) . . ?
C11 C12 C13 103.20(11) . . ?
C12 O4 H4O 108(2) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C13 C12 107.14(12) . . ?
C14 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
C14 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.5 . . ?
O1 C14 C13 108.36(13) . . ?
O1 C14 C15 103.16(10) . . ?
C13 C14 C15 107.59(12) . . ?
O1 C14 H14 112.4 . . ?
C13 C14 H14 112.4 . . ?
C15 C14 H14 112.4 . . ?
C11 C15 C2 114.92(11) . . ?
C11 C15 C14 102.19(11) . . ?
C2 C15 C14 102.50(11) . . ?
C11 C15 H15 112.1 . . ?
C2 C15 H15 112.1 . . ?
C14 C15 H15 112.1 . . ?

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
C14 O1 C1 O2 -179.60(13) . . . . ?
C14 O1 C1 C2 2.52(15) . . . . ?
O2 C1 C2 C3 23.4(2) . . . . ?
O1 C1 C2 C3 -158.97(11) . . . . ?
O2 C1 C2 C15 158.84(15) . . . . ?
O1 C1 C2 C15 -23.52(13) . . . . ?
C15 C2 C3 C8 -3.9(2) . . . . ?
C1 C2 C3 C8 120.54(15) . . . . ?
C15 C2 C3 C4 169.78(12) . . . . ?
C1 C2 C3 C4 -65.73(15) . . . . ?
C8 C3 C4 C5 -23.87(19) . . . . ?
C2 C3 C4 C5 162.09(11) . . . . ?
C3 C4 C5 C16 177.19(12) . . . . ?
C3 C4 C5 C6 54.15(15) . . . . ?
C6 C5 C16 C18 -106.25(16) . . . . ?
C4 C5 C16 C18 132.96(15) . . . . ?
C6 C5 C16 C17 71.09(16) . . . . ?
C4 C5 C16 C17 -49.70(18) . . . . ?
C16 C5 C6 C7 178.75(12) . . . . ?
C4 C5 C6 C7 -56.22(15) . . . . ?
C5 C6 C7 O3 -153.51(14) . . . . ?
C5 C6 C7 C8 28.95(18) . . . . ?
C2 C3 C8 C7 166.22(13) . . . . ?
C4 C3 C8 C7 -6.9(2) . . . . ?
C2 C3 C8 C9 -7.4(2) . . . . ?
C4 C3 C8 C9 179.48(14) . . . . ?
O3 C7 C8 C3 -173.25(14) . . . . ?
C6 C7 C8 C3 4.3(2) . . . . ?
O3 C7 C8 C9 1.4(2) . . . . ?
C6 C7 C8 C9 178.87(13) . . . . ?
C3 C8 C9 C10 -36.1(2) . . . . ?
C7 C8 C9 C10 149.96(13) . . . . ?
C8 C9 C10 C11 55.5(2) . . . . ?
C8 C9 C10 O5 -14.76(19) . . . . ?
C9 C10 O5 C11 112.51(14) . . . . ?
C10 O5 C11 C15 -113.83(13) . . . . ?
C10 O5 C11 C12 116.22(14) . . . . ?
C9 C10 C11 O5 -106.68(15) . . . . ?
O5 C10 C11 C15 104.08(14) . . . . ?
C9 C10 C11 C15 -2.6(2) . . . . ?
O5 C10 C11 C12 -104.06(14) . . . . ?
C9 C10 C11 C12 149.26(14) . . . . ?
O5 C11 C12 O4 -16.85(17) . . . . ?
C10 C11 C12 O4 54.41(19) . . . . ?
C15 C11 C12 O4 -150.44(12) . . . . ?
O5 C11 C12 C19 -135.03(13) . . . . ?
C10 C11 C12 C19 -63.77(18) . . . . ?
C15 C11 C12 C19 91.38(14) . . . . ?
O5 C11 C12 C13 105.68(13) . . . . ?
C10 C11 C12 C13 176.95(13) . . . . ?
C15 C11 C12 C13 -27.91(15) . . . . ?
O4 C12 C13 C14 131.35(13) . . . . ?
C19 C12 C13 C14 -108.65(15) . . . . ?
C11 C12 C13 C14 9.26(16) . . . . ?
C1 O1 C14 C13 133.46(12) . . . . ?
C1 O1 C14 C15 19.59(14) . . . . ?
C12 C13 C14 O1 -99.06(14) . . . . ?
C12 C13 C14 C15 11.85(17) . . . . ?
O5 C11 C15 C2 11.18(17) . . . . ?
C10 C11 C15 C2 -59.03(18) . . . . ?
C12 C11 C15 C2 145.14(12) . . . . ?
O5 C11 C15 C14 -98.98(13) . . . . ?
C10 C11 C15 C14 -169.19(13) . . . . ?
C12 C11 C15 C14 34.99(14) . . . . ?
C3 C2 C15 C11 54.29(18) . . . . ?
C1 C2 C15 C11 -76.18(13) . . . . ?
C3 C2 C15 C14 164.26(12) . . . . ?
C1 C2 C15 C14 33.79(12) . . . . ?
O1 C14 C15 C11 86.14(12) . . . . ?
C13 C14 C15 C11 -28.29(14) . . . . ?
O1 C14 C15 C2 -33.17(13) . . . . ?
C13 C14 C15 C2 -147.59(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O4 1.00 2.43 3.2893(17) 143.6 1_455
C6 H6A O1 0.99 2.55 3.4282(18) 147.3 2_656
C10 H10 O2 1.00 2.43 3.2055(18) 133.5 2_756
O4 H4O O3 0.83(2) 2.04(2) 2.8276(19) 158(3) 2_746

_refine_diff_density_max         0.732
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.108


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate, Heptane, Benzene'
####################################################################### 
# 
# 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_rac06
_database_code_depnum_ccdc_archive 'CCDC 1061012'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 O6'
_chemical_formula_weight         346.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   8.2576(3)
_cell_length_b                   10.4049(4)
_cell_length_c                   19.0995(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641.02(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9870
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      38.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_T_max  0.7487
_exptl_absorpt_process_details   'SADABS-2014/4 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            85501
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         43.738
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12633
_reflns_number_gt                10319
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'APEX2 v2014.9-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+0.0894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3972 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.35(16)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         12633
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.05480(10) 0.60250(8) 0.12791(4) 0.01582(14) Uani 1 1 d . . . . .
C1 C 0.97038(12) 0.53258(10) 0.17467(5) 0.01259(15) Uani 1 1 d . . . . .
O2 O 1.03818(11) 0.45991(9) 0.21425(5) 0.01827(15) Uani 1 1 d . . . . .
C2 C 0.78920(12) 0.55644(9) 0.16810(5) 0.01054(14) Uani 1 1 d . . . . .
H2 H 0.7285 0.4750 0.1588 0.013 Uiso 1 1 calc R U . . .
C3 C 0.71592(11) 0.63197(9) 0.23110(5) 0.00966(13) Uani 1 1 d . . . . .
O5 O 0.73755(9) 0.76435(7) 0.21128(3) 0.00961(11) Uani 1 1 d . . . . .
C4 C 0.80081(12) 0.61211(10) 0.30079(5) 0.01183(14) Uani 1 1 d . . . . .
H4A H 0.9174 0.6316 0.2952 0.014 Uiso 1 1 calc R U . . .
H4B H 0.7909 0.5208 0.3147 0.014 Uiso 1 1 calc R U . . .
C5 C 0.73097(13) 0.69680(10) 0.35904(5) 0.01256(15) Uani 1 1 d . . . . .
H5 H 0.7440 0.7884 0.3443 0.015 Uiso 1 1 calc R U . . .
C16 C 0.82769(14) 0.67776(10) 0.42533(5) 0.01434(16) Uani 1 1 d . . . . .
C17 C 0.98409(17) 0.75136(13) 0.42875(6) 0.0217(2) Uani 1 1 d . . . . .
H17A H 1.0447 0.7253 0.4705 0.033 Uiso 1 1 calc R U . . .
H17B H 0.9609 0.8436 0.4311 0.033 Uiso 1 1 calc R U . . .
H17C H 1.0487 0.7331 0.3869 0.033 Uiso 1 1 calc R U . . .
C18 C 0.78196(17) 0.59998(12) 0.47720(6) 0.01901(19) Uani 1 1 d . . . . .
H18A H 0.8487 0.5902 0.5174 0.023 Uiso 1 1 calc R U . . .
H18B H 0.6826 0.5543 0.4740 0.023 Uiso 1 1 calc R U . . .
C6 C 0.54835(13) 0.66990(11) 0.36612(6) 0.01567(17) Uani 1 1 d . . . . .
H6A H 0.5304 0.5794 0.3801 0.019 Uiso 1 1 calc R U . . .
H6B H 0.5007 0.7264 0.4024 0.019 Uiso 1 1 calc R U . . .
C7 C 0.47010(12) 0.69541(10) 0.29656(6) 0.01404(16) Uani 1 1 d . . . . .
O3 O 0.37282(12) 0.78144(9) 0.28699(5) 0.02211(18) Uani 1 1 d . . . . .
C8 C 0.53033(12) 0.61163(10) 0.23615(5) 0.01182(14) Uani 1 1 d . . . . .
H8 H 0.5077 0.5194 0.2471 0.014 Uiso 1 1 calc R U . . .
C9 C 0.44511(12) 0.64806(11) 0.16768(6) 0.01420(16) Uani 1 1 d . . . . .
H9A H 0.4510 0.5741 0.1352 0.017 Uiso 1 1 calc R U . . .
H9B H 0.3293 0.6644 0.1777 0.017 Uiso 1 1 calc R U . . .
C10 C 0.51569(12) 0.76551(10) 0.13146(5) 0.01234(15) Uani 1 1 d . . . . .
O6 O 0.43365(10) 0.83920(10) 0.09714(5) 0.01996(16) Uani 1 1 d . . . . .
C11 C 0.69958(11) 0.77294(9) 0.13794(5) 0.00982(13) Uani 1 1 d . . . . .
C12 C 0.80070(12) 0.88681(10) 0.11016(5) 0.01171(14) Uani 1 1 d . . . . .
O4 O 0.78475(10) 0.99692(8) 0.15327(4) 0.01461(13) Uani 1 1 d D . . . .
H4O H 0.817(2) 0.979(2) 0.1914(10) 0.022 Uiso 1 1 d D U . . .
C19 C 0.75716(15) 0.92752(12) 0.03587(6) 0.01678(18) Uani 1 1 d . . . . .
H19A H 0.6468 0.9622 0.0352 0.025 Uiso 1 1 calc R U . . .
H19B H 0.7635 0.8529 0.0047 0.025 Uiso 1 1 calc R U . . .
H19C H 0.8332 0.9937 0.0199 0.025 Uiso 1 1 calc R U . . .
C13 C 0.97319(12) 0.82872(10) 0.11210(6) 0.01374(15) Uani 1 1 d . . . . .
H13A H 1.0463 0.8753 0.0798 0.016 Uiso 1 1 calc R U . . .
H13B H 1.0188 0.8329 0.1600 0.016 Uiso 1 1 calc R U . . .
C14 C 0.95137(12) 0.68916(10) 0.08879(5) 0.01287(15) Uani 1 1 d . . . . .
H14 H 0.9716 0.6805 0.0374 0.015 Uiso 1 1 calc R U . . .
C15 C 0.77532(11) 0.65068(9) 0.10671(5) 0.01027(13) Uani 1 1 d . . . . .
H15 H 0.7139 0.6154 0.0659 0.012 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3464(14) . ?
O1 C14 1.4494(13) . ?
C1 O2 1.2070(13) . ?
C1 C2 1.5217(14) . ?
C2 C15 1.5328(13) . ?
C2 C3 1.5593(13) . ?
C2 H2 1.0000 . ?
C3 O5 1.4396(12) . ?
C3 C4 1.5185(13) . ?
C3 C8 1.5501(13) . ?
O5 C11 1.4381(11) . ?
C4 C5 1.5318(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C16 1.5101(15) . ?
C5 C6 1.5397(15) . ?
C5 H5 1.0000 . ?
C16 C18 1.3338(15) . ?
C16 C17 1.5029(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C6 C7 1.5010(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.2165(14) . ?
C7 C8 1.5292(14) . ?
C8 C9 1.5326(15) . ?
C8 H8 1.0000 . ?
C9 C10 1.5204(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O6 1.2150(13) . ?
C10 C11 1.5255(13) . ?
C11 C15 1.5379(13) . ?
C11 C12 1.5436(13) . ?
C12 O4 1.4169(13) . ?
C12 C19 1.5238(14) . ?
C12 C13 1.5477(14) . ?
O4 H4O 0.797(17) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C13 C14 1.5296(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5462(14) . ?
C14 H14 1.0000 . ?
C15 H15 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 O1 C14 111.90(8) . . ?
O2 C1 O1 120.92(10) . . ?
O2 C1 C2 127.58(10) . . ?
O1 C1 C2 111.48(8) . . ?
C1 C2 C15 103.94(8) . . ?
C1 C2 C3 113.59(7) . . ?
C15 C2 C3 103.82(7) . . ?
C1 C2 H2 111.7 . . ?
C15 C2 H2 111.7 . . ?
C3 C2 H2 111.7 . . ?
O5 C3 C4 107.67(7) . . ?
O5 C3 C8 105.65(8) . . ?
C4 C3 C8 112.54(8) . . ?
O5 C3 C2 103.36(7) . . ?
C4 C3 C2 115.38(8) . . ?
C8 C3 C2 111.27(7) . . ?
C11 O5 C3 106.77(7) . . ?
C3 C4 C5 112.61(8) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C16 C5 C4 109.53(8) . . ?
C16 C5 C6 114.87(8) . . ?
C4 C5 C6 109.15(8) . . ?
C16 C5 H5 107.7 . . ?
C4 C5 H5 107.7 . . ?
C6 C5 H5 107.7 . . ?
C18 C16 C17 121.35(10) . . ?
C18 C16 C5 123.55(11) . . ?
C17 C16 C5 115.09(9) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 120.0 . . ?
C16 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C7 C6 C5 108.16(8) . . ?
C7 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
C7 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O3 C7 C6 123.18(10) . . ?
O3 C7 C8 121.40(10) . . ?
C6 C7 C8 115.28(9) . . ?
C7 C8 C9 110.70(9) . . ?
C7 C8 C3 106.90(8) . . ?
C9 C8 C3 111.54(8) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C3 C8 H8 109.2 . . ?
C10 C9 C8 114.27(8) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
O6 C10 C9 122.61(9) . . ?
O6 C10 C11 124.53(10) . . ?
C9 C10 C11 112.67(8) . . ?
O5 C11 C10 107.03(7) . . ?
O5 C11 C15 103.75(7) . . ?
C10 C11 C15 109.36(8) . . ?
O5 C11 C12 105.34(7) . . ?
C10 C11 C12 123.33(8) . . ?
C15 C11 C12 106.36(8) . . ?
O4 C12 C19 107.12(8) . . ?
O4 C12 C11 111.75(8) . . ?
C19 C12 C11 113.94(8) . . ?
O4 C12 C13 112.79(8) . . ?
C19 C12 C13 110.36(9) . . ?
C11 C12 C13 100.94(8) . . ?
C12 O4 H4O 108.3(15) . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C13 C12 104.80(8) . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
O1 C14 C13 111.79(8) . . ?
O1 C14 C15 106.19(8) . . ?
C13 C14 C15 106.98(8) . . ?
O1 C14 H14 110.6 . . ?
C13 C14 H14 110.6 . . ?
C15 C14 H14 110.6 . . ?
C2 C15 C11 105.24(7) . . ?
C2 C15 C14 105.35(7) . . ?
C11 C15 C14 104.72(8) . . ?
C2 C15 H15 113.5 . . ?
C11 C15 H15 113.5 . . ?
C14 C15 H15 113.5 . . ?

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
C14 O1 C1 O2 -176.30(10) . . . . ?
C14 O1 C1 C2 5.14(12) . . . . ?
O2 C1 C2 C15 -176.46(10) . . . . ?
O1 C1 C2 C15 1.98(10) . . . . ?
O2 C1 C2 C3 71.40(13) . . . . ?
O1 C1 C2 C3 -110.16(9) . . . . ?
C1 C2 C3 O5 87.64(9) . . . . ?
C15 C2 C3 O5 -24.57(9) . . . . ?
C1 C2 C3 C4 -29.62(12) . . . . ?
C15 C2 C3 C4 -141.83(8) . . . . ?
C1 C2 C3 C8 -159.41(8) . . . . ?
C15 C2 C3 C8 88.38(9) . . . . ?
C4 C3 O5 C11 163.62(7) . . . . ?
C8 C3 O5 C11 -75.92(8) . . . . ?
C2 C3 O5 C11 41.07(9) . . . . ?
O5 C3 C4 C5 60.78(10) . . . . ?
C8 C3 C4 C5 -55.23(11) . . . . ?
C2 C3 C4 C5 175.59(8) . . . . ?
C3 C4 C5 C16 -176.57(8) . . . . ?
C3 C4 C5 C6 56.88(11) . . . . ?
C4 C5 C16 C18 -98.21(13) . . . . ?
C6 C5 C16 C18 25.02(15) . . . . ?
C4 C5 C16 C17 80.52(12) . . . . ?
C6 C5 C16 C17 -156.25(10) . . . . ?
C16 C5 C6 C7 178.99(9) . . . . ?
C4 C5 C6 C7 -57.58(11) . . . . ?
C5 C6 C7 O3 -114.46(12) . . . . ?
C5 C6 C7 C8 61.17(12) . . . . ?
O3 C7 C8 C9 -3.01(14) . . . . ?
C6 C7 C8 C9 -178.72(8) . . . . ?
O3 C7 C8 C3 118.66(11) . . . . ?
C6 C7 C8 C3 -57.06(11) . . . . ?
O5 C3 C8 C7 -65.30(9) . . . . ?
C4 C3 C8 C7 51.92(10) . . . . ?
C2 C3 C8 C7 -176.81(8) . . . . ?
O5 C3 C8 C9 55.83(10) . . . . ?
C4 C3 C8 C9 173.05(8) . . . . ?
C2 C3 C8 C9 -55.68(11) . . . . ?
C7 C8 C9 C10 80.85(11) . . . . ?
C3 C8 C9 C10 -38.03(12) . . . . ?
C8 C9 C10 O6 -147.94(11) . . . . ?
C8 C9 C10 C11 36.97(12) . . . . ?
C3 O5 C11 C10 75.12(9) . . . . ?
C3 O5 C11 C15 -40.47(9) . . . . ?
C3 O5 C11 C12 -152.05(7) . . . . ?
O6 C10 C11 O5 131.33(11) . . . . ?
C9 C10 C11 O5 -53.70(11) . . . . ?
O6 C10 C11 C15 -116.89(12) . . . . ?
C9 C10 C11 C15 58.08(11) . . . . ?
O6 C10 C11 C12 9.15(16) . . . . ?
C9 C10 C11 C12 -175.88(9) . . . . ?
O5 C11 C12 O4 -48.50(10) . . . . ?
C10 C11 C12 O4 74.44(11) . . . . ?
C15 C11 C12 O4 -158.22(8) . . . . ?
O5 C11 C12 C19 -170.10(8) . . . . ?
C10 C11 C12 C19 -47.15(13) . . . . ?
C15 C11 C12 C19 80.18(10) . . . . ?
O5 C11 C12 C13 71.63(9) . . . . ?
C10 C11 C12 C13 -165.42(9) . . . . ?
C15 C11 C12 C13 -38.09(9) . . . . ?
O4 C12 C13 C14 158.08(8) . . . . ?
C19 C12 C13 C14 -82.15(10) . . . . ?
C11 C12 C13 C14 38.69(9) . . . . ?
C1 O1 C14 C13 106.34(10) . . . . ?
C1 O1 C14 C15 -9.99(11) . . . . ?
C12 C13 C14 O1 -141.52(8) . . . . ?
C12 C13 C14 C15 -25.67(10) . . . . ?
C1 C2 C15 C11 -117.99(8) . . . . ?
C3 C2 C15 C11 1.06(9) . . . . ?
C1 C2 C15 C14 -7.63(9) . . . . ?
C3 C2 C15 C14 111.42(8) . . . . ?
O5 C11 C15 C2 22.86(9) . . . . ?
C10 C11 C15 C2 -91.07(9) . . . . ?
C12 C11 C15 C2 133.69(8) . . . . ?
O5 C11 C15 C14 -87.95(8) . . . . ?
C10 C11 C15 C14 158.12(8) . . . . ?
C12 C11 C15 C14 22.89(9) . . . . ?
O1 C14 C15 C2 10.64(10) . . . . ?
C13 C14 C15 C2 -108.89(8) . . . . ?
O1 C14 C15 C11 121.37(8) . . . . ?
C13 C14 C15 C11 1.84(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O3 1.00 2.41 3.2731(13) 143.6 3_645
C6 H6A O6 0.99 2.55 3.5149(15) 163.6 3_645
C9 H9B O1 0.99 2.54 3.3451(13) 138.2 1_455
O4 H4O O2 0.797(17) 2.171(17) 2.9477(12) 164.6(19) 3_755
C19 H19A O6 0.98 2.48 3.0578(15) 117.7 .
C14 H14 O6 1.00 2.60 3.5664(14) 163.4 4_565

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate, Heptane, Benzene'
####################################################################### 
# 
# 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_rac10
_database_code_depnum_ccdc_archive 'CCDC 1061013'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Br O5'
_chemical_formula_weight         411.28

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.6137(4)
_cell_length_b                   9.3584(5)
_cell_length_c                   24.1592(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1721.39(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9810
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      37.12

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.416
_shelx_estimated_absorpt_T_min   0.378
_shelx_estimated_absorpt_T_max   0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_T_max  0.7478
_exptl_absorpt_process_details   'SADABS-2014/4 (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker KAPPA APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            51998
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.334
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             8272
_reflns_number_gt                7574
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.980

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

_computing_data_collection       'APEX2 v2014.9-0 (Bruker-AXS, 2014)'
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2013)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0289P)²+0.0363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3023 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.014(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8272
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0625
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.63451(14) 0.62093(12) 0.71588(4) 0.01358(18) Uani 1 1 d . . . . .
C1 C 0.48231(17) 0.61085(16) 0.68712(5) 0.0113(2) Uani 1 1 d . . . . .
O2 O 0.38402(15) 0.71029(12) 0.68272(4) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.45834(16) 0.46188(14) 0.66416(5) 0.0098(2) Uani 1 1 d . . . . .
H2 H 0.3367 0.4256 0.6709 0.012 Uiso 1 1 calc R U . . .
C3 C 0.51136(15) 0.44727(15) 0.60170(5) 0.0083(2) Uani 1 1 d . . . . .
O5 O 0.69277(11) 0.40385(10) 0.60411(4) 0.00778(16) Uani 1 1 d . . . . .
C4 C 0.50239(16) 0.58369(15) 0.56808(5) 0.0104(2) Uani 1 1 d . . . . .
H4A H 0.5792 0.6564 0.5854 0.013 Uiso 1 1 calc R U . . .
H4B H 0.3806 0.6206 0.5688 0.013 Uiso 1 1 calc R U . . .
C5 C 0.55896(16) 0.56180(16) 0.50772(5) 0.0107(2) Uani 1 1 d . . . . .
H5 H 0.6841 0.5293 0.5081 0.013 Uiso 1 1 calc R U . . .
C6 C 0.44889(18) 0.44112(16) 0.48195(6) 0.0134(2) Uani 1 1 d . . . . .
H6A H 0.3250 0.4723 0.4792 0.016 Uiso 1 1 calc R U . . .
H6B H 0.4919 0.4217 0.4440 0.016 Uiso 1 1 calc R U . . .
C7 C 0.45835(16) 0.30642(16) 0.51547(6) 0.0117(2) Uani 1 1 d . . . . .
O3 O 0.50005(18) 0.19191(13) 0.49554(5) 0.0193(2) Uani 1 1 d . . . . .
C8 C 0.41043(16) 0.32116(15) 0.57603(5) 0.0104(2) Uani 1 1 d . . . . .
H8 H 0.2823 0.3441 0.5781 0.013 Uiso 1 1 calc R U . . .
C9 C 0.44112(17) 0.18463(15) 0.60929(6) 0.0122(2) Uani 1 1 d . . . . .
H9A H 0.4023 0.1014 0.5872 0.015 Uiso 1 1 calc R U . . .
H9B H 0.3691 0.1877 0.6434 0.015 Uiso 1 1 calc R U . . .
C10 C 0.63472(17) 0.16534(14) 0.62510(6) 0.0114(2) Uani 1 1 d . . . . .
H10 H 0.7020 0.1439 0.5905 0.014 Uiso 1 1 calc R U . . .
Br1 Br 0.64560(2) -0.00416(2) 0.67287(2) 0.01929(4) Uani 1 1 d . . . . .
C11 C 0.70781(16) 0.30346(14) 0.64968(5) 0.0084(2) Uani 1 1 d . . . . .
C12 C 0.90051(16) 0.32182(16) 0.66851(5) 0.0111(2) Uani 1 1 d . . . . .
O4 O 1.02077(12) 0.30674(13) 0.62394(4) 0.01398(19) Uani 1 1 d D . . . .
H4O H 0.973(3) 0.345(2) 0.5936(8) 0.021 Uiso 1 1 d D U . . .
C13 C 0.89513(16) 0.47402(16) 0.69262(6) 0.0136(3) Uani 1 1 d . . . . .
H13A H 0.9934 0.4894 0.7188 0.016 Uiso 1 1 calc R U . . .
H13B H 0.9022 0.5464 0.6628 0.016 Uiso 1 1 calc R U . . .
C14 C 0.71760(16) 0.48243(16) 0.72261(5) 0.0120(2) Uani 1 1 d . . . . .
H14 H 0.7323 0.4596 0.7628 0.014 Uiso 1 1 calc R U . . .
C15 C 0.59482(16) 0.37202(15) 0.69466(5) 0.0095(2) Uani 1 1 d . . . . .
H15 H 0.5427 0.3016 0.7211 0.011 Uiso 1 1 calc R U . . .
C16 C 0.55023(17) 0.69695(17) 0.47277(6) 0.0146(2) Uani 1 1 d . . . . .
C17 C 0.5870(2) 0.6771(2) 0.41174(6) 0.0219(3) Uani 1 1 d . . . . .
H17A H 0.4884 0.6268 0.3944 0.033 Uiso 1 1 calc R U . . .
H17B H 0.6946 0.6209 0.4071 0.033 Uiso 1 1 calc R U . . .
H17C H 0.6019 0.7708 0.3942 0.033 Uiso 1 1 calc R U . . .
C18 C 0.5173(2) 0.82494(18) 0.49352(8) 0.0201(3) Uani 1 1 d . . . . .
H18A H 0.5165 0.9063 0.4700 0.024 Uiso 1 1 calc R U . . .
H18B H 0.4944 0.8356 0.5320 0.024 Uiso 1 1 calc R U . . .
C19 C 0.96213(19) 0.21786(19) 0.71277(7) 0.0183(3) Uani 1 1 d . . . . .
H19A H 0.9719 0.1219 0.6968 0.027 Uiso 1 1 calc R U . . .
H19B H 0.8772 0.2164 0.7432 0.027 Uiso 1 1 calc R U . . .
H19C H 1.0770 0.2482 0.7268 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3544(17) . ?
O1 C14 1.4514(18) . ?
C1 O2 1.1989(18) . ?
C1 C2 1.5115(19) . ?
C2 C15 1.5264(19) . ?
C2 C3 1.5679(18) . ?
C2 H2 1.0000 . ?
C3 O5 1.4409(14) . ?
C3 C4 1.515(2) . ?
C3 C8 1.5388(18) . ?
O5 C11 1.4519(16) . ?
C4 C5 1.5342(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C16 1.522(2) . ?
C5 C6 1.538(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.500(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O3 1.2170(17) . ?
C7 C8 1.5142(19) . ?
C8 C9 1.527(2) . ?
C8 H8 1.0000 . ?
C9 C10 1.5334(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5275(19) . ?
C10 Br1 1.9635(13) . ?
C10 H10 1.0000 . ?
C11 C15 1.5273(18) . ?
C11 C12 1.5456(17) . ?
C12 O4 1.4205(16) . ?
C12 C19 1.520(2) . ?
C12 C13 1.539(2) . ?
O4 H4O 0.893(18) . ?
C13 C14 1.5356(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5484(19) . ?
C14 H14 1.0000 . ?
C15 H15 1.0000 . ?
C16 C18 1.322(2) . ?
C16 C17 1.512(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C1 O1 C14 111.60(11) . . ?
O2 C1 O1 121.69(13) . . ?
O2 C1 C2 127.45(13) . . ?
O1 C1 C2 110.85(11) . . ?
C1 C2 C15 104.40(11) . . ?
C1 C2 C3 113.74(11) . . ?
C15 C2 C3 103.96(10) . . ?
C1 C2 H2 111.4 . . ?
C15 C2 H2 111.4 . . ?
C3 C2 H2 111.4 . . ?
O5 C3 C4 107.61(10) . . ?
O5 C3 C8 106.18(10) . . ?
C4 C3 C8 114.06(11) . . ?
O5 C3 C2 103.45(10) . . ?
C4 C3 C2 115.53(11) . . ?
C8 C3 C2 109.04(10) . . ?
C3 O5 C11 106.78(9) . . ?
C3 C4 C5 112.61(11) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C16 C5 C4 113.83(12) . . ?
C16 C5 C6 111.21(11) . . ?
C4 C5 C6 109.26(11) . . ?
C16 C5 H5 107.4 . . ?
C4 C5 H5 107.4 . . ?
C6 C5 H5 107.4 . . ?
C7 C6 C5 111.86(11) . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O3 C7 C6 122.61(13) . . ?
O3 C7 C8 121.70(13) . . ?
C6 C7 C8 115.69(12) . . ?
C7 C8 C9 113.28(12) . . ?
C7 C8 C3 109.82(11) . . ?
C9 C8 C3 110.68(11) . . ?
C7 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C3 C8 H8 107.6 . . ?
C8 C9 C10 112.12(11) . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 110.33(11) . . ?
C11 C10 Br1 116.09(9) . . ?
C9 C10 Br1 106.38(9) . . ?
C11 C10 H10 107.9 . . ?
C9 C10 H10 107.9 . . ?
Br1 C10 H10 107.9 . . ?
O5 C11 C15 102.90(10) . . ?
O5 C11 C10 102.94(10) . . ?
C15 C11 C10 115.27(11) . . ?
O5 C11 C12 103.07(10) . . ?
C15 C11 C12 106.18(10) . . ?
C10 C11 C12 123.66(11) . . ?
O4 C12 C19 105.71(11) . . ?
O4 C12 C13 113.32(11) . . ?
C19 C12 C13 109.53(12) . . ?
O4 C12 C11 112.19(11) . . ?
C19 C12 C11 115.40(12) . . ?
C13 C12 C11 100.89(10) . . ?
C12 O4 H4O 108.7(15) . . ?
C14 C13 C12 104.44(11) . . ?
C14 C13 H13A 110.9 . . ?
C12 C13 H13A 110.9 . . ?
C14 C13 H13B 110.9 . . ?
C12 C13 H13B 110.9 . . ?
H13A C13 H13B 108.9 . . ?
O1 C14 C13 112.12(12) . . ?
O1 C14 C15 106.49(10) . . ?
C13 C14 C15 106.94(11) . . ?
O1 C14 H14 110.4 . . ?
C13 C14 H14 110.4 . . ?
C15 C14 H14 110.4 . . ?
C2 C15 C11 105.75(10) . . ?
C2 C15 C14 104.71(11) . . ?
C11 C15 C14 104.51(10) . . ?
C2 C15 H15 113.6 . . ?
C11 C15 H15 113.6 . . ?
C14 C15 H15 113.6 . . ?
C18 C16 C17 121.05(15) . . ?
C18 C16 C5 123.41(15) . . ?
C17 C16 C5 115.52(14) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 120.0 . . ?
C16 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C12 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C12 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C14 O1 C1 O2 171.18(12) . . . . ?
C14 O1 C1 C2 -7.77(14) . . . . ?
O2 C1 C2 C15 -165.39(13) . . . . ?
O1 C1 C2 C15 13.48(14) . . . . ?
O2 C1 C2 C3 81.97(16) . . . . ?
O1 C1 C2 C3 -99.16(12) . . . . ?
C1 C2 C3 O5 92.31(12) . . . . ?
C15 C2 C3 O5 -20.60(12) . . . . ?
C1 C2 C3 C4 -25.01(14) . . . . ?
C15 C2 C3 C4 -137.92(11) . . . . ?
C1 C2 C3 C8 -155.00(11) . . . . ?
C15 C2 C3 C8 92.08(12) . . . . ?
C4 C3 O5 C11 162.08(10) . . . . ?
C8 C3 O5 C11 -75.41(12) . . . . ?
C2 C3 O5 C11 39.34(12) . . . . ?
O5 C3 C4 C5 64.07(13) . . . . ?
C8 C3 C4 C5 -53.44(13) . . . . ?
C2 C3 C4 C5 179.03(10) . . . . ?
C3 C4 C5 C16 179.64(10) . . . . ?
C3 C4 C5 C6 54.66(13) . . . . ?
C16 C5 C6 C7 179.13(11) . . . . ?
C4 C5 C6 C7 -54.39(15) . . . . ?
C5 C6 C7 O3 -126.40(14) . . . . ?
C5 C6 C7 C8 54.29(15) . . . . ?
O3 C7 C8 C9 6.81(18) . . . . ?
C6 C7 C8 C9 -173.87(11) . . . . ?
O3 C7 C8 C3 131.12(14) . . . . ?
C6 C7 C8 C3 -49.56(14) . . . . ?
O5 C3 C8 C7 -69.79(13) . . . . ?
C4 C3 C8 C7 48.54(14) . . . . ?
C2 C3 C8 C7 179.34(10) . . . . ?
O5 C3 C8 C9 56.02(13) . . . . ?
C4 C3 C8 C9 174.35(10) . . . . ?
C2 C3 C8 C9 -54.86(13) . . . . ?
C7 C8 C9 C10 79.81(14) . . . . ?
C3 C8 C9 C10 -44.03(14) . . . . ?
C8 C9 C10 C11 48.25(14) . . . . ?
C8 C9 C10 Br1 174.95(9) . . . . ?
C3 O5 C11 C15 -41.94(12) . . . . ?
C3 O5 C11 C10 78.19(11) . . . . ?
C3 O5 C11 C12 -152.22(10) . . . . ?
C9 C10 C11 O5 -62.73(12) . . . . ?
Br1 C10 C11 O5 176.18(7) . . . . ?
C9 C10 C11 C15 48.48(15) . . . . ?
Br1 C10 C11 C15 -72.60(13) . . . . ?
C9 C10 C11 C12 -178.32(11) . . . . ?
Br1 C10 C11 C12 60.60(14) . . . . ?
O5 C11 C12 O4 -52.81(14) . . . . ?
C15 C11 C12 O4 -160.63(12) . . . . ?
C10 C11 C12 O4 62.71(17) . . . . ?
O5 C11 C12 C19 -173.97(12) . . . . ?
C15 C11 C12 C19 78.21(15) . . . . ?
C10 C11 C12 C19 -58.45(17) . . . . ?
O5 C11 C12 C13 68.11(11) . . . . ?
C15 C11 C12 C13 -39.71(13) . . . . ?
C10 C11 C12 C13 -176.37(12) . . . . ?
O4 C12 C13 C14 159.21(11) . . . . ?
C19 C12 C13 C14 -83.03(13) . . . . ?
C11 C12 C13 C14 39.09(12) . . . . ?
C1 O1 C14 C13 115.35(12) . . . . ?
C1 O1 C14 C15 -1.29(14) . . . . ?
C12 C13 C14 O1 -141.44(11) . . . . ?
C12 C13 C14 C15 -25.07(14) . . . . ?
C1 C2 C15 C11 -123.39(11) . . . . ?
C3 C2 C15 C11 -3.91(13) . . . . ?
C1 C2 C15 C14 -13.32(12) . . . . ?
C3 C2 C15 C14 106.15(11) . . . . ?
O5 C11 C15 C2 26.87(13) . . . . ?
C10 C11 C15 C2 -84.37(13) . . . . ?
C12 C11 C15 C2 134.81(11) . . . . ?
O5 C11 C15 C14 -83.34(11) . . . . ?
C10 C11 C15 C14 165.42(11) . . . . ?
C12 C11 C15 C14 24.60(14) . . . . ?
O1 C14 C15 C2 9.44(13) . . . . ?
C13 C14 C15 C2 -110.61(12) . . . . ?
O1 C14 C15 C11 120.40(11) . . . . ?
C13 C14 C15 C11 0.35(14) . . . . ?
C4 C5 C16 C18 7.60(19) . . . . ?
C6 C5 C16 C18 131.52(15) . . . . ?
C4 C5 C16 C17 -174.03(12) . . . . ?
C6 C5 C16 C17 -50.10(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O4 1.00 2.31 3.1874(15) 146.5 1_455
O4 H4O O5 0.893(18) 2.22(2) 2.7004(14) 113.4(17) .
O4 H4O O3 0.893(18) 2.19(2) 2.8908(16) 135.0(19) 4_556
C15 H15 O1 1.00 2.65 3.6389(17) 172.5 3_646
C15 H15 O2 1.00 2.54 3.3305(17) 136.0 3_646
C19 H19A Br1 0.98 2.81 3.3248(17) 113.5 .

_refine_diff_density_max         0.746
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate, Heptane, Benzene'
####################################################################### 
# 
# 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_a14286
_database_code_depnum_ccdc_archive 'CCDC 1061014'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;
_audit_creation_date             2014-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846),
 SHELXL-2014,
 and manual edit
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H24 O5'
_chemical_formula_sum            'C19 H24 O5'
_chemical_formula_weight         332.38
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.2703(9)
_cell_length_b                   11.2931(16)
_cell_length_c                   23.177(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.96
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0571 before and 0.0492 after correction.
The Ratio of minimum to maximum transmission is 0.8611.
The λ/2 correction factor is 0.00150.
;
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 0.00 0.1140
0.00 1.00 0.00 0.0640
-2.00 -1.00 1.00 0.2680
2.00 0.00 -1.00 0.2550
0.00 0.00 -1.00 0.0030
0.00 0.00 1.00 0.0170
2.00 -8.00 -1.00 0.1360
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blade
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            42176
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         33.933
_diffrn_reflns_theta_min         1.757
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_source_target            Mo
_diffrn_radiation_wavelength     0.71073
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                5479
_reflns_number_total             6378
_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_data_collection       'APEX2 2014.5-0 (Bruker-AXS, 2007)'
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_structure_solution    'XT-2014/1 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/3 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 2130 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(2)
_refine_ls_abs_structure_Hooft   -0.6(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.447
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         6378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.447
_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)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0831
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60147(17) 0.38434(9) 0.46552(5) 0.0183(2) Uani 1 1 d . . . . .
O2 O 0.7616(2) 0.34388(10) 0.35657(5) 0.0243(3) Uani 1 1 d . . . . .
H2 H 0.629(5) 0.328(2) 0.3652(11) 0.050(7) Uiso 1 1 d . . . . .
O3 O 0.43551(17) 0.62722(10) 0.44133(4) 0.0179(2) Uani 1 1 d . . . . .
O4 O 0.26855(17) 0.58723(10) 0.52373(5) 0.0212(2) Uani 1 1 d . . . . .
O5 O 0.8278(2) 0.28834(10) 0.65931(5) 0.0252(3) Uani 1 1 d . . . . .
C1 C 0.7876(2) 0.45191(12) 0.44797(6) 0.0146(3) Uani 1 1 d . . . . .
C2 C 0.7890(2) 0.57950(12) 0.46746(6) 0.0134(2) Uani 1 1 d . . . . .
H2A H 0.936(4) 0.6063(19) 0.4700(10) 0.037(6) Uiso 1 1 d . . . . .
C3 C 0.6612(2) 0.60975(12) 0.52169(5) 0.0121(2) Uani 1 1 d . . . . .
H3 H 0.676(3) 0.6945(15) 0.5272(7) 0.013(4) Uiso 1 1 d . . . . .
C4 C 0.7127(2) 0.55487(12) 0.58083(6) 0.0124(2) Uani 1 1 d . . . . .
H4 H 0.862(3) 0.5757(15) 0.5899(7) 0.008(4) Uiso 1 1 d . . . . .
C5 C 0.6987(2) 0.41806(12) 0.58441(6) 0.0161(3) Uani 1 1 d . . . . .
H5 H 0.549(3) 0.3966(16) 0.5724(8) 0.018(5) Uiso 1 1 d . . . . .
C6 C 0.8602(3) 0.35128(14) 0.54757(7) 0.0229(3) Uani 1 1 d . . . . .
H6A H 1.004(3) 0.3871(16) 0.5545(8) 0.021(5) Uiso 1 1 d . . . . .
H6B H 0.865(3) 0.2724(17) 0.5610(8) 0.024(5) Uiso 1 1 d . . . . .
C7 C 0.8155(3) 0.34815(13) 0.48377(6) 0.0202(3) Uani 1 1 d . . . . .
H7 H 0.857(3) 0.2753(16) 0.4627(7) 0.014(4) Uiso 1 1 d . . . . .
C8 C 0.8198(2) 0.45267(13) 0.38266(6) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.6780(3) 0.55912(15) 0.36501(6) 0.0203(3) Uani 1 1 d . . . . .
H9A H 0.738(3) 0.6011(17) 0.3323(8) 0.024(5) Uiso 1 1 d . . . . .
H9B H 0.542(4) 0.5320(19) 0.3527(9) 0.029(5) Uiso 1 1 d . . . . .
C10 C 0.6548(2) 0.63631(13) 0.41907(6) 0.0161(3) Uani 1 1 d . . . . .
H10 H 0.682(3) 0.7182(16) 0.4126(7) 0.013(4) Uiso 1 1 d . . . . .
C11 C 0.4342(2) 0.60300(12) 0.49886(6) 0.0153(3) Uani 1 1 d . . . . .
C12 C 0.5729(2) 0.61462(13) 0.62695(6) 0.0153(3) Uani 1 1 d . . . . .
H12A H 0.587(3) 0.6992(17) 0.6239(8) 0.018(4) Uiso 1 1 d . . . . .
H12B H 0.424(3) 0.5975(16) 0.6195(8) 0.020(5) Uiso 1 1 d . . . . .
C13 C 0.6261(2) 0.57484(13) 0.68893(6) 0.0156(3) Uani 1 1 d . . . . .
H13 H 0.519(3) 0.6103(15) 0.7144(7) 0.014(4) Uiso 1 1 d . . . . .
C14 C 0.5961(3) 0.44006(14) 0.69216(6) 0.0192(3) Uani 1 1 d . . . . .
H14A H 0.634(3) 0.4104(16) 0.7310(8) 0.019(4) Uiso 1 1 d . . . . .
H14B H 0.433(4) 0.423(2) 0.6848(10) 0.040(6) Uiso 1 1 d . . . . .
C15 C 0.7206(3) 0.37435(13) 0.64686(6) 0.0179(3) Uani 1 1 d . . . . .
C16 C 1.0532(3) 0.47240(15) 0.36731(7) 0.0214(3) Uani 1 1 d . . . . .
H16A H 1.145(4) 0.4137(19) 0.3839(9) 0.031(5) Uiso 1 1 d . . . . .
H16B H 1.109(3) 0.5461(18) 0.3832(8) 0.024(5) Uiso 1 1 d . . . . .
H16C H 1.068(3) 0.4740(16) 0.3273(9) 0.023(5) Uiso 1 1 d . . . . .
C17 C 0.8415(2) 0.61913(14) 0.70905(6) 0.0161(3) Uani 1 1 d . . . . .
C18 C 0.8503(3) 0.74981(15) 0.72048(8) 0.0263(3) Uani 1 1 d . . . . .
H18A H 0.819(3) 0.7938(19) 0.6859(10) 0.036(6) Uiso 1 1 d . . . . .
H18B H 0.997(4) 0.7730(18) 0.7331(10) 0.034(6) Uiso 1 1 d . . . . .
H18C H 0.741(4) 0.770(2) 0.7496(10) 0.042(6) Uiso 1 1 d . . . . .
C19 C 1.0102(3) 0.55096(17) 0.71833(8) 0.0247(3) Uani 1 1 d . . . . .
H19A H 1.137(4) 0.587(2) 0.7323(9) 0.035(5) Uiso 1 1 d . . . . .
H19B H 1.009(4) 0.470(2) 0.7118(9) 0.036(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4523(18) . ?
O1 C7 1.465(2) . ?
O2 H2 0.87(3) . ?
O2 C8 1.4172(18) . ?
O3 C10 1.4725(18) . ?
O3 C11 1.3611(17) . ?
O4 C11 1.2015(18) . ?
O5 C15 1.2160(19) . ?
C1 C2 1.5101(19) . ?
C1 C7 1.446(2) . ?
C1 C8 1.527(2) . ?
C2 H2A 0.97(2) . ?
C2 C3 1.5290(19) . ?
C2 C10 1.542(2) . ?
C3 H3 0.970(17) . ?
C3 C4 1.5385(19) . ?
C3 C11 1.5205(19) . ?
C4 H4 0.987(18) . ?
C4 C5 1.5497(19) . ?
C4 C12 1.5383(19) . ?
C5 H5 1.010(19) . ?
C5 C6 1.524(2) . ?
C5 C15 1.5356(19) . ?
C6 H6A 1.00(2) . ?
C6 H6B 0.944(19) . ?
C6 C7 1.505(2) . ?
C7 H7 0.990(18) . ?
C8 C9 1.550(2) . ?
C8 C16 1.522(2) . ?
C9 H9A 0.970(19) . ?
C9 H9B 0.95(2) . ?
C9 C10 1.533(2) . ?
C10 H10 0.952(18) . ?
C12 H12A 0.961(19) . ?
C12 H12B 0.97(2) . ?
C12 C13 1.542(2) . ?
C13 H13 0.981(18) . ?
C13 C14 1.536(2) . ?
C13 C17 1.514(2) . ?
C14 H14A 0.991(18) . ?
C14 H14B 1.05(2) . ?
C14 C15 1.504(2) . ?
C16 H16A 0.96(2) . ?
C16 H16B 0.98(2) . ?
C16 H16C 0.93(2) . ?
C17 C18 1.500(2) . ?
C17 C19 1.326(2) . ?
C18 H18A 0.96(2) . ?
C18 H18B 1.00(2) . ?
C18 H18C 0.99(2) . ?
C19 H19A 0.95(2) . ?
C19 H19B 0.93(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
C1 O1 C7 59.43(9) . . ?
C8 O2 H2 109.1(16) . . ?
C11 O3 C10 111.27(11) . . ?
O1 C1 C2 114.97(11) . . ?
O1 C1 C8 112.77(12) . . ?
C2 C1 C8 106.88(11) . . ?
C7 C1 O1 60.74(10) . . ?
C7 C1 C2 126.92(12) . . ?
C7 C1 C8 123.85(13) . . ?
C1 C2 H2A 108.7(13) . . ?
C1 C2 C3 117.13(11) . . ?
C1 C2 C10 100.15(11) . . ?
C3 C2 H2A 112.2(13) . . ?
C3 C2 C10 102.68(11) . . ?
C10 C2 H2A 115.6(13) . . ?
C2 C3 H3 106.1(10) . . ?
C2 C3 C4 122.18(11) . . ?
C4 C3 H3 105.1(10) . . ?
C11 C3 C2 101.12(11) . . ?
C11 C3 H3 100.8(10) . . ?
C11 C3 C4 119.10(12) . . ?
C3 C4 H4 107.0(9) . . ?
C3 C4 C5 115.93(11) . . ?
C5 C4 H4 106.2(10) . . ?
C12 C4 C3 108.83(11) . . ?
C12 C4 H4 106.7(9) . . ?
C12 C4 C5 111.58(12) . . ?
C4 C5 H5 106.1(10) . . ?
C6 C5 C4 115.19(13) . . ?
C6 C5 H5 110.2(10) . . ?
C6 C5 C15 108.03(12) . . ?
C15 C5 C4 111.45(11) . . ?
C15 C5 H5 105.4(10) . . ?
C5 C6 H6A 108.0(11) . . ?
C5 C6 H6B 107.6(12) . . ?
H6A C6 H6B 107.5(16) . . ?
C7 C6 C5 115.99(14) . . ?
C7 C6 H6A 109.5(11) . . ?
C7 C6 H6B 107.8(12) . . ?
O1 C7 C6 116.57(13) . . ?
O1 C7 H7 109.1(10) . . ?
C1 C7 O1 59.83(9) . . ?
C1 C7 C6 124.54(13) . . ?
C1 C7 H7 115.0(10) . . ?
C6 C7 H7 117.0(10) . . ?
O2 C8 C1 112.57(12) . . ?
O2 C8 C9 114.32(13) . . ?
O2 C8 C16 105.96(13) . . ?
C1 C8 C9 100.95(11) . . ?
C16 C8 C1 111.10(12) . . ?
C16 C8 C9 112.09(13) . . ?
C8 C9 H9A 111.3(11) . . ?
C8 C9 H9B 110.2(13) . . ?
H9A C9 H9B 105.8(17) . . ?
C10 C9 C8 106.24(11) . . ?
C10 C9 H9A 113.4(11) . . ?
C10 C9 H9B 110.0(13) . . ?
O3 C10 C2 103.03(11) . . ?
O3 C10 C9 109.59(12) . . ?
O3 C10 H10 107.0(10) . . ?
C2 C10 H10 114.8(10) . . ?
C9 C10 C2 107.82(12) . . ?
C9 C10 H10 113.9(10) . . ?
O3 C11 C3 109.00(12) . . ?
O4 C11 O3 120.33(13) . . ?
O4 C11 C3 130.53(13) . . ?
C4 C12 H12A 109.4(11) . . ?
C4 C12 H12B 109.7(11) . . ?
C4 C12 C13 113.34(12) . . ?
H12A C12 H12B 105.9(16) . . ?
C13 C12 H12A 109.8(11) . . ?
C13 C12 H12B 108.5(11) . . ?
C12 C13 H13 107.1(10) . . ?
C14 C13 C12 107.93(12) . . ?
C14 C13 H13 106.9(10) . . ?
C17 C13 C12 112.57(12) . . ?
C17 C13 H13 106.9(11) . . ?
C17 C13 C14 114.95(13) . . ?
C13 C14 H14A 110.5(11) . . ?
C13 C14 H14B 107.1(12) . . ?
H14A C14 H14B 108.6(16) . . ?
C15 C14 C13 113.04(12) . . ?
C15 C14 H14A 110.0(11) . . ?
C15 C14 H14B 107.4(12) . . ?
O5 C15 C5 122.00(13) . . ?
O5 C15 C14 121.02(13) . . ?
C14 C15 C5 116.94(13) . . ?
C8 C16 H16A 112.6(13) . . ?
C8 C16 H16B 112.6(12) . . ?
C8 C16 H16C 109.2(12) . . ?
H16A C16 H16B 102.8(17) . . ?
H16A C16 H16C 110.6(17) . . ?
H16B C16 H16C 108.9(16) . . ?
C18 C17 C13 114.35(14) . . ?
C19 C17 C13 124.73(15) . . ?
C19 C17 C18 120.88(16) . . ?
C17 C18 H18A 110.7(13) . . ?
C17 C18 H18B 110.1(12) . . ?
C17 C18 H18C 109.0(14) . . ?
H18A C18 H18B 107.1(18) . . ?
H18A C18 H18C 107.8(18) . . ?
H18B C18 H18C 112.1(17) . . ?
C17 C19 H19A 118.4(14) . . ?
C17 C19 H19B 122.6(15) . . ?
H19A C19 H19B 119(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O5 0.87(3) 2.37(3) 3.1244(19) 145(2) 4_456
C2 H2A O4 0.97(2) 2.44(2) 3.2790(18) 144.5(17) 1_655
C3 H3 O3 0.970(17) 2.688(17) 3.5378(17) 146.5(13) 4_566
C6 H6B O1 0.944(19) 2.39(2) 3.0758(19) 129.3(15) 4_556
C16 H16B O3 0.98(2) 2.61(2) 3.427(2) 140.8(16) 1_655

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
O1 C1 C2 C3 25.82(17) . . . . ?
O1 C1 C2 C10 -84.19(13) . . . . ?
O1 C1 C7 C6 -103.18(18) . . . . ?
O1 C1 C8 O2 -35.68(17) . . . . ?
O1 C1 C8 C9 86.65(14) . . . . ?
O1 C1 C8 C16 -154.33(12) . . . . ?
O2 C8 C9 C10 143.34(13) . . . . ?
C1 O1 C7 C6 116.27(15) . . . . ?
C1 C2 C3 C4 61.50(17) . . . . ?
C1 C2 C3 C11 -73.68(14) . . . . ?
C1 C2 C10 O3 89.58(12) . . . . ?
C1 C2 C10 C9 -26.26(15) . . . . ?
C1 C8 C9 C10 22.25(15) . . . . ?
C2 C1 C7 O1 100.62(16) . . . . ?
C2 C1 C7 C6 -2.6(3) . . . . ?
C2 C1 C8 O2 -162.97(12) . . . . ?
C2 C1 C8 C9 -40.64(14) . . . . ?
C2 C1 C8 C16 78.38(15) . . . . ?
C2 C3 C4 C5 -59.89(17) . . . . ?
C2 C3 C4 C12 173.39(12) . . . . ?
C2 C3 C11 O3 -27.05(14) . . . . ?
C2 C3 C11 O4 157.47(15) . . . . ?
C3 C2 C10 O3 -31.42(13) . . . . ?
C3 C2 C10 C9 -147.27(12) . . . . ?
C3 C4 C5 C6 64.81(17) . . . . ?
C3 C4 C5 C15 -171.66(12) . . . . ?
C3 C4 C12 C13 -174.53(12) . . . . ?
C4 C3 C11 O3 -163.99(11) . . . . ?
C4 C3 C11 O4 20.5(2) . . . . ?
C4 C5 C6 C7 -75.40(18) . . . . ?
C4 C5 C15 O5 -137.70(15) . . . . ?
C4 C5 C15 C14 44.60(18) . . . . ?
C4 C12 C13 C14 -58.76(16) . . . . ?
C4 C12 C13 C17 69.16(16) . . . . ?
C5 C4 C12 C13 56.30(15) . . . . ?
C5 C6 C7 O1 -13.7(2) . . . . ?
C5 C6 C7 C1 56.5(2) . . . . ?
C6 C5 C15 O5 -10.2(2) . . . . ?
C6 C5 C15 C14 172.10(14) . . . . ?
C7 O1 C1 C2 -119.91(14) . . . . ?
C7 O1 C1 C8 117.21(14) . . . . ?
C7 C1 C2 C3 -45.2(2) . . . . ?
C7 C1 C2 C10 -155.26(15) . . . . ?
C7 C1 C8 O2 33.4(2) . . . . ?
C7 C1 C8 C9 155.75(15) . . . . ?
C7 C1 C8 C16 -85.23(18) . . . . ?
C8 C1 C2 C3 151.80(12) . . . . ?
C8 C1 C2 C10 41.79(14) . . . . ?
C8 C1 C7 O1 -99.12(15) . . . . ?
C8 C1 C7 C6 157.70(15) . . . . ?
C8 C9 C10 O3 -109.06(13) . . . . ?
C8 C9 C10 C2 2.41(16) . . . . ?
C10 O3 C11 O4 -176.63(13) . . . . ?
C10 O3 C11 C3 7.35(15) . . . . ?
C10 C2 C3 C4 170.06(12) . . . . ?
C10 C2 C3 C11 34.87(13) . . . . ?
C11 O3 C10 C2 15.50(14) . . . . ?
C11 O3 C10 C9 130.07(12) . . . . ?
C11 C3 C4 C5 67.78(16) . . . . ?
C11 C3 C4 C12 -58.94(15) . . . . ?
C12 C4 C5 C6 -169.87(12) . . . . ?
C12 C4 C5 C15 -46.34(16) . . . . ?
C12 C13 C14 C15 53.98(16) . . . . ?
C12 C13 C17 C18 71.11(16) . . . . ?
C12 C13 C17 C19 -111.20(17) . . . . ?
C13 C14 C15 O5 132.62(15) . . . . ?
C13 C14 C15 C5 -49.66(18) . . . . ?
C14 C13 C17 C18 -164.76(13) . . . . ?
C14 C13 C17 C19 12.9(2) . . . . ?
C15 C5 C6 C7 159.27(14) . . . . ?
C16 C8 C9 C10 -96.06(15) . . . . ?
C17 C13 C14 C15 -72.57(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate, Heptane, Benzene'
####################################################################### 
# 
# 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_p15149
_database_code_depnum_ccdc_archive 'CCDC 1061016'
_audit_update_record             
;
2015-04-21 deposited with the CCDC.
2016-08-17 downloaded from the CCDC.
;
_audit_creation_date             2015-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998),
 SHELXL-2014,
 and manual edit
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H24 O5'
_chemical_formula_sum            'C19 H24 O5'
_chemical_formula_weight         332.38
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4079(3)
_cell_length_b                   14.7042(4)
_cell_length_c                   21.8592(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3345.33(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.78
_cell_measurement_theta_min      3.62
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  0.9591
_exptl_absorpt_correction_T_min  0.8890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1022 before and 0.0782 after correction.
The Ratio of minimum to maximum transmission is 0.9269.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl Acetate, Heptane, Benzene'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 -1.00 0.0070
0.00 0.00 1.00 0.0230
1.00 -2.00 0.00 0.0490
-1.00 2.00 0.00 0.0550
2.00 2.00 1.00 0.0520
1.00 -1.00 1.00 0.0460
1.00 2.00 0.00 0.0460
1.00 -4.00 3.00 0.0390
-3.00 -2.00 -1.00 0.0270
4.00 3.00 -2.00 0.0510
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            46504
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         79.108
_diffrn_reflns_theta_min         3.623
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_source_voltage           50
_diffrn_special_details          
'Half shutterless; half correlated due to detector issues.'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                6111
_reflns_number_total             7174
_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_data_collection       'APEX2 2014.9-0 (Bruker-AXS, 2007)'
_computing_cell_refinement       'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.34A (Bruker-AXS, 2007)'
_computing_structure_solution    'XT-2014/4 (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_abs_structure_Hooft   -0.04(9)
_refine_ls_extinction_coef       .

_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         7174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.059
_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)+(0.0335P)²+0.4541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0832
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O -0.03492(18) 0.56047(13) 0.60617(9) 0.0257(4) Uani 1 1 d . . . . .
O2 O 0.0555(2) 0.41629(12) 0.48143(9) 0.0272(5) Uani 1 1 d . . . . .
O1 O 0.15419(18) 0.40753(12) 0.57144(8) 0.0224(4) Uani 1 1 d . . . . .
O4 O 0.0871(2) 0.60085(16) 0.71685(10) 0.0344(5) Uani 1 1 d . . . . .
H4 H 0.017(4) 0.571(3) 0.699(2) 0.075(15) Uiso 1 1 d . . . . .
O3 O -0.0571(2) 0.77121(13) 0.43577(10) 0.0317(5) Uani 1 1 d . . . . .
C15 C 0.2655(3) 0.54941(17) 0.57380(12) 0.0186(5) Uani 1 1 d . . . . .
H15 H 0.353(3) 0.5708(19) 0.5753(13) 0.017(7) Uiso 1 1 d . . . . .
C11 C 0.1808(3) 0.61455(18) 0.61256(12) 0.0217(6) Uani 1 1 d . . . . .
H11 H 0.214(3) 0.676(2) 0.6082(13) 0.023(8) Uiso 1 1 d . . . . .
C10 C 0.0462(3) 0.61450(18) 0.58779(12) 0.0215(6) Uani 1 1 d . . . . .
C9 C 0.0164(3) 0.67917(19) 0.53641(13) 0.0239(6) Uani 1 1 d . . . . .
H9A H 0.070(3) 0.735(2) 0.5401(15) 0.036(9) Uiso 1 1 d . . . . .
H9B H -0.072(3) 0.698(2) 0.5393(14) 0.026(8) Uiso 1 1 d . . . . .
C8 C 0.0406(3) 0.63525(18) 0.47397(13) 0.0209(6) Uani 1 1 d . . . . .
H8 H -0.011(3) 0.5833(19) 0.4697(13) 0.019(7) Uiso 1 1 d . . . . .
C3 C 0.1797(3) 0.60187(17) 0.46347(12) 0.0183(5) Uani 1 1 d . . . . .
H3 H 0.240(3) 0.6536(19) 0.4701(12) 0.018(7) Uiso 1 1 d . . . . .
C2 C 0.2245(3) 0.52704(17) 0.50825(11) 0.0189(5) Uani 1 1 d . . . . .
H2 H 0.297(3) 0.4986(18) 0.4893(12) 0.014(7) Uiso 1 1 d . . . . .
C1 C 0.1339(3) 0.44637(17) 0.51635(12) 0.0205(5) Uani 1 1 d . . . . .
C14 C 0.2533(3) 0.45637(18) 0.60602(12) 0.0216(5) Uani 1 1 d . . . . .
H14 H 0.331(3) 0.419(2) 0.6025(13) 0.021(7) Uiso 1 1 d . . . . .
C13 C 0.2058(3) 0.4732(2) 0.67087(13) 0.0270(6) Uani 1 1 d . . . . .
H13A H 0.265(3) 0.446(2) 0.7015(14) 0.026(8) Uiso 1 1 d . . . . .
H13B H 0.124(3) 0.446(2) 0.6779(14) 0.029(9) Uiso 1 1 d . . . . .
C12 C 0.1930(3) 0.5771(2) 0.67840(12) 0.0253(6) Uani 1 1 d . . . . .
C19 C 0.3109(4) 0.6171(3) 0.70917(15) 0.0386(8) Uani 1 1 d . . . . .
H19A H 0.300(3) 0.683(2) 0.7103(15) 0.038(9) Uiso 1 1 d . . . . .
H19B H 0.394(4) 0.602(3) 0.6863(19) 0.054(12) Uiso 1 1 d . . . . .
H19C H 0.316(3) 0.592(2) 0.7510(17) 0.042(10) Uiso 1 1 d . . . . .
C7 C -0.0028(3) 0.70064(19) 0.42368(13) 0.0236(6) Uani 1 1 d . . . . .
C6 C 0.0214(3) 0.6700(2) 0.35906(13) 0.0258(6) Uani 1 1 d . . . . .
H6A H -0.003(4) 0.721(3) 0.3291(17) 0.054(12) Uiso 1 1 d . . . . .
H6B H -0.033(4) 0.621(2) 0.3506(16) 0.038(10) Uiso 1 1 d . . . . .
C5 C 0.1611(3) 0.63940(18) 0.34952(12) 0.0228(6) Uani 1 1 d . . . . .
H5 H 0.170(3) 0.609(2) 0.3072(14) 0.024(8) Uiso 1 1 d . . . . .
C4 C 0.1945(3) 0.56703(18) 0.39723(12) 0.0225(6) Uani 1 1 d . . . . .
H4A H 0.285(3) 0.546(2) 0.3924(13) 0.020(7) Uiso 1 1 d . . . . .
H4B H 0.136(3) 0.513(2) 0.3910(14) 0.023(8) Uiso 1 1 d . . . . .
C16 C 0.2568(3) 0.71734(18) 0.34857(12) 0.0216(6) Uani 1 1 d . . . . .
C18 C 0.2241(3) 0.8035(2) 0.35596(13) 0.0255(6) Uani 1 1 d . . . . .
H18A H 0.287(3) 0.853(2) 0.3529(14) 0.028(8) Uiso 1 1 d . . . . .
H18B H 0.131(3) 0.823(2) 0.3630(14) 0.028(8) Uiso 1 1 d . . . . .
C17 C 0.3936(3) 0.6906(2) 0.33625(15) 0.0283(6) Uani 1 1 d . . . . .
H17A H 0.434(4) 0.665(3) 0.3753(18) 0.056(12) Uiso 1 1 d . . . . .
H17B H 0.454(4) 0.747(2) 0.3236(16) 0.044(10) Uiso 1 1 d . . . . .
H17C H 0.403(4) 0.647(3) 0.3024(18) 0.051(11) Uiso 1 1 d . . . . .
O5B O 0.5907(2) 0.50022(12) 0.60452(9) 0.0262(4) Uani 1 1 d . . . . .
O2B O 0.40407(18) 0.34681(13) 0.49667(9) 0.0239(4) Uani 1 1 d . . . . .
O1B O 0.48604(18) 0.29282(13) 0.58299(8) 0.0230(4) Uani 1 1 d . . . . .
O4B O 0.7648(2) 0.44953(14) 0.70004(9) 0.0308(5) Uani 1 1 d . . . . .
H4BA H 0.699(4) 0.484(3) 0.6858(18) 0.050(12) Uiso 1 1 d . . . . .
O3B O 0.7316(2) 0.59914(14) 0.40281(9) 0.0348(5) Uani 1 1 d . . . . .
C15B C 0.7109(3) 0.30487(17) 0.56261(12) 0.0189(5) Uani 1 1 d . . . . .
H15B H 0.782(3) 0.2630(17) 0.5594(11) 0.010(6) Uiso 1 1 d . . . . .
C11B C 0.7628(3) 0.39347(18) 0.59232(12) 0.0207(5) Uani 1 1 d . . . . .
H11B H 0.846(3) 0.4023(19) 0.5804(13) 0.018(7) Uiso 1 1 d . . . . .
C10B C 0.6814(3) 0.47391(17) 0.57380(12) 0.0214(5) Uani 1 1 d . . . . .
C9B C 0.7138(3) 0.51781(19) 0.51349(13) 0.0257(6) Uani 1 1 d . . . . .
H9BA H 0.804(3) 0.5140(19) 0.5062(13) 0.021(8) Uiso 1 1 d . . . . .
H9BB H 0.687(3) 0.582(2) 0.5157(14) 0.029(8) Uiso 1 1 d . . . . .
C8B C 0.6436(3) 0.47390(18) 0.45923(12) 0.0197(5) Uani 1 1 d . . . . .
H8B H 0.551(3) 0.4784(19) 0.4640(13) 0.019(7) Uiso 1 1 d . . . . .
C3B C 0.6732(3) 0.37204(18) 0.44942(12) 0.0196(5) Uani 1 1 d . . . . .
H3B H 0.768(3) 0.3641(19) 0.4428(12) 0.018(7) Uiso 1 1 d . . . . .
C2B C 0.6339(3) 0.30974(17) 0.50267(12) 0.0184(5) Uani 1 1 d . . . . .
H2B H 0.632(3) 0.247(2) 0.4867(13) 0.024(8) Uiso 1 1 d . . . . .
C1B C 0.4968(3) 0.31980(16) 0.52432(12) 0.0198(5) Uani 1 1 d . . . . .
C14B C 0.6109(3) 0.26871(18) 0.60892(13) 0.0216(6) Uani 1 1 d . . . . .
H14B H 0.615(3) 0.202(2) 0.6113(15) 0.037(9) Uiso 1 1 d . . . . .
C13B C 0.6306(3) 0.3186(2) 0.66917(13) 0.0237(6) Uani 1 1 d . . . . .
H13C H 0.632(3) 0.277(2) 0.7065(15) 0.029(9) Uiso 1 1 d . . . . .
H13D H 0.559(3) 0.3649(18) 0.6748(12) 0.012(7) Uiso 1 1 d . . . . .
C12B C 0.7577(3) 0.37126(18) 0.66164(12) 0.0224(6) Uani 1 1 d . . . . .
C19B C 0.8711(3) 0.3120(2) 0.68043(15) 0.0315(7) Uani 1 1 d . . . . .
H19D H 0.947(4) 0.341(2) 0.6706(15) 0.034(9) Uiso 1 1 d . . . . .
H19E H 0.871(4) 0.251(3) 0.6616(17) 0.045(11) Uiso 1 1 d . . . . .
H19F H 0.869(3) 0.304(2) 0.7259(15) 0.028(8) Uiso 1 1 d . . . . .
C7B C 0.6724(3) 0.52828(18) 0.40098(12) 0.0232(6) Uani 1 1 d . . . . .
C6B C 0.6177(3) 0.4909(2) 0.34202(13) 0.0250(6) Uani 1 1 d . . . . .
H6BA H 0.650(3) 0.531(2) 0.3082(14) 0.025(8) Uiso 1 1 d . . . . .
H6BB H 0.522(4) 0.495(2) 0.3449(15) 0.037(9) Uiso 1 1 d . . . . .
C5B C 0.6462(3) 0.3892(2) 0.33323(12) 0.0247(6) Uani 1 1 d . . . . .
H5B H 0.592(3) 0.368(2) 0.2994(15) 0.032(9) Uiso 1 1 d . . . . .
C4B C 0.6049(3) 0.33846(19) 0.39122(13) 0.0229(6) Uani 1 1 d . . . . .
H4BB H 0.622(3) 0.276(2) 0.3867(13) 0.023(8) Uiso 1 1 d . . . . .
H4BC H 0.505(3) 0.3464(19) 0.3980(12) 0.019(7) Uiso 1 1 d . . . . .
C16B C 0.7820(3) 0.3661(2) 0.31480(12) 0.0292(7) Uani 1 1 d . . . . .
C18B C 0.8741(3) 0.4257(3) 0.30882(16) 0.0402(8) Uani 1 1 d . . . . .
H18C H 0.965(4) 0.409(3) 0.2945(18) 0.059(12) Uiso 1 1 d . . . . .
H18D H 0.863(3) 0.486(2) 0.3113(14) 0.021(8) Uiso 1 1 d . . . . .
C17B C 0.8048(4) 0.2666(2) 0.30363(15) 0.0382(8) Uani 1 1 d . . . . .
H17D H 0.813(3) 0.230(2) 0.3454(15) 0.039(9) Uiso 1 1 d . . . . .
H17E H 0.887(4) 0.256(2) 0.2804(16) 0.035(9) Uiso 1 1 d . . . . .
H17F H 0.735(4) 0.241(2) 0.2756(17) 0.050(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C10 1.227(3) . ?
O2 C1 1.201(3) . ?
O1 C1 1.349(3) . ?
O1 C14 1.467(3) . ?
O4 H4 0.94(5) . ?
O4 C12 1.429(3) . ?
O3 C7 1.211(3) . ?
C15 H15 0.96(3) . ?
C15 C11 1.553(4) . ?
C15 C2 1.531(4) . ?
C15 C14 1.544(3) . ?
C11 H11 0.97(3) . ?
C11 C10 1.503(4) . ?
C11 C12 1.546(4) . ?
C10 C9 1.504(4) . ?
C9 H9A 1.00(4) . ?
C9 H9B 0.96(3) . ?
C9 C8 1.531(4) . ?
C8 H8 0.94(3) . ?
C8 C3 1.545(4) . ?
C8 C7 1.529(4) . ?
C3 H3 1.00(3) . ?
C3 C2 1.545(3) . ?
C3 C4 1.544(4) . ?
C2 H2 0.96(3) . ?
C2 C1 1.526(4) . ?
C14 H14 0.97(3) . ?
C14 C13 1.522(4) . ?
C13 H13A 0.99(3) . ?
C13 H13B 0.96(3) . ?
C13 C12 1.542(4) . ?
C12 C19 1.518(4) . ?
C19 H19A 0.98(4) . ?
C19 H19B 1.02(4) . ?
C19 H19C 0.98(4) . ?
C7 C6 1.504(4) . ?
C6 H6A 1.03(4) . ?
C6 H6B 0.94(4) . ?
C6 C5 1.536(4) . ?
C5 H5 1.03(3) . ?
C5 C4 1.530(4) . ?
C5 C16 1.519(4) . ?
C4 H4A 1.00(3) . ?
C4 H4B 1.00(3) . ?
C16 C18 1.322(4) . ?
C16 C17 1.501(4) . ?
C18 H18A 0.98(3) . ?
C18 H18B 1.02(3) . ?
C17 H17A 1.03(4) . ?
C17 H17B 1.07(4) . ?
C17 H17C 0.99(4) . ?
O5B C10B 1.221(3) . ?
O2B C1B 1.206(3) . ?
O1B C1B 1.347(3) . ?
O1B C14B 1.461(3) . ?
O4B H4BA 0.90(4) . ?
O4B C12B 1.426(3) . ?
O3B C7B 1.211(3) . ?
C15B H15B 0.96(3) . ?
C15B C11B 1.552(4) . ?
C15B C2B 1.538(4) . ?
C15B C14B 1.547(4) . ?
C11B H11B 0.91(3) . ?
C11B C10B 1.510(4) . ?
C11B C12B 1.551(4) . ?
C10B C9B 1.506(4) . ?
C9B H9BA 0.95(3) . ?
C9B H9BB 0.99(3) . ?
C9B C8B 1.535(4) . ?
C8B H8B 0.97(3) . ?
C8B C3B 1.544(4) . ?
C8B C7B 1.533(4) . ?
C3B H3B 1.00(3) . ?
C3B C2B 1.537(4) . ?
C3B C4B 1.539(4) . ?
C2B H2B 0.99(3) . ?
C2B C1B 1.511(4) . ?
C14B H14B 0.98(3) . ?
C14B C13B 1.522(4) . ?
C13B H13C 1.02(3) . ?
C13B H13D 1.02(3) . ?
C13B C12B 1.541(4) . ?
C12B C19B 1.523(4) . ?
C19B H19D 0.92(4) . ?
C19B H19E 0.98(4) . ?
C19B H19F 1.00(3) . ?
C7B C6B 1.512(4) . ?
C6B H6BA 1.00(3) . ?
C6B H6BB 1.00(4) . ?
C6B C5B 1.537(4) . ?
C5B H5B 0.98(3) . ?
C5B C4B 1.532(4) . ?
C5B C16B 1.508(4) . ?
C4B H4BB 0.94(3) . ?
C4B H4BC 1.05(3) . ?
C16B C18B 1.305(5) . ?
C16B C17B 1.503(5) . ?
C18B H18C 1.03(4) . ?
C18B H18D 0.89(3) . ?
C17B H17D 1.07(3) . ?
C17B H17E 1.00(4) . ?
C17B H17F 1.02(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C14 111.3(2) . . ?
C12 O4 H4 104(3) . . ?
C11 C15 H15 108.3(17) . . ?
C2 C15 H15 111.4(17) . . ?
C2 C15 C11 119.0(2) . . ?
C2 C15 C14 102.3(2) . . ?
C14 C15 H15 110.6(17) . . ?
C14 C15 C11 104.5(2) . . ?
C15 C11 H11 108.4(18) . . ?
C10 C11 C15 109.4(2) . . ?
C10 C11 H11 107.4(18) . . ?
C10 C11 C12 114.3(2) . . ?
C12 C11 C15 104.0(2) . . ?
C12 C11 H11 113.1(17) . . ?
O5 C10 C11 121.6(2) . . ?
O5 C10 C9 120.8(3) . . ?
C11 C10 C9 117.4(2) . . ?
C10 C9 H9A 110.1(19) . . ?
C10 C9 H9B 109.0(18) . . ?
C10 C9 C8 111.4(2) . . ?
H9A C9 H9B 108(3) . . ?
C8 C9 H9A 109(2) . . ?
C8 C9 H9B 109.5(18) . . ?
C9 C8 H8 109.7(18) . . ?
C9 C8 C3 114.9(2) . . ?
C3 C8 H8 105.4(17) . . ?
C7 C8 C9 109.1(2) . . ?
C7 C8 H8 105.7(18) . . ?
C7 C8 C3 111.7(2) . . ?
C8 C3 H3 108.9(16) . . ?
C2 C3 C8 114.5(2) . . ?
C2 C3 H3 105.2(16) . . ?
C4 C3 C8 109.8(2) . . ?
C4 C3 H3 109.1(16) . . ?
C4 C3 C2 109.1(2) . . ?
C15 C2 C3 121.6(2) . . ?
C15 C2 H2 106.2(16) . . ?
C3 C2 H2 106.0(16) . . ?
C1 C2 C15 103.3(2) . . ?
C1 C2 C3 116.2(2) . . ?
C1 C2 H2 101.4(16) . . ?
O2 C1 O1 121.2(2) . . ?
O2 C1 C2 129.2(2) . . ?
O1 C1 C2 109.6(2) . . ?
O1 C14 C15 104.9(2) . . ?
O1 C14 H14 105.5(17) . . ?
O1 C14 C13 109.3(2) . . ?
C15 C14 H14 113.0(17) . . ?
C13 C14 C15 107.9(2) . . ?
C13 C14 H14 115.6(18) . . ?
C14 C13 H13A 111.3(18) . . ?
C14 C13 H13B 111.8(19) . . ?
C14 C13 C12 106.8(2) . . ?
H13A C13 H13B 106(3) . . ?
C12 C13 H13A 112.3(18) . . ?
C12 C13 H13B 109.0(19) . . ?
O4 C12 C11 113.4(2) . . ?
O4 C12 C13 111.8(2) . . ?
O4 C12 C19 105.5(2) . . ?
C13 C12 C11 105.1(2) . . ?
C19 C12 C11 109.9(2) . . ?
C19 C12 C13 111.2(3) . . ?
C12 C19 H19A 108(2) . . ?
C12 C19 H19B 113(2) . . ?
C12 C19 H19C 108(2) . . ?
H19A C19 H19B 109(3) . . ?
H19A C19 H19C 110(3) . . ?
H19B C19 H19C 109(3) . . ?
O3 C7 C8 121.3(3) . . ?
O3 C7 C6 122.7(3) . . ?
C6 C7 C8 115.9(2) . . ?
C7 C6 H6A 110(2) . . ?
C7 C6 H6B 108(2) . . ?
C7 C6 C5 112.0(2) . . ?
H6A C6 H6B 107(3) . . ?
C5 C6 H6A 111(2) . . ?
C5 C6 H6B 109(2) . . ?
C6 C5 H5 109.8(17) . . ?
C4 C5 C6 109.0(2) . . ?
C4 C5 H5 106.5(17) . . ?
C16 C5 C6 113.7(2) . . ?
C16 C5 H5 104.9(17) . . ?
C16 C5 C4 112.7(2) . . ?
C3 C4 H4A 107.4(17) . . ?
C3 C4 H4B 109.2(17) . . ?
C5 C4 C3 112.7(2) . . ?
C5 C4 H4A 111.0(17) . . ?
C5 C4 H4B 108.6(17) . . ?
H4A C4 H4B 108(2) . . ?
C18 C16 C5 123.6(3) . . ?
C18 C16 C17 121.1(3) . . ?
C17 C16 C5 115.3(2) . . ?
C16 C18 H18A 121.9(19) . . ?
C16 C18 H18B 122.2(18) . . ?
H18A C18 H18B 116(3) . . ?
C16 C17 H17A 110(2) . . ?
C16 C17 H17B 113(2) . . ?
C16 C17 H17C 113(2) . . ?
H17A C17 H17B 105(3) . . ?
H17A C17 H17C 110(3) . . ?
H17B C17 H17C 105(3) . . ?
C1B O1B C14B 111.5(2) . . ?
C12B O4B H4BA 102(2) . . ?
C11B C15B H15B 107.5(16) . . ?
C2B C15B H15B 111.5(15) . . ?
C2B C15B C11B 119.9(2) . . ?
C2B C15B C14B 102.9(2) . . ?
C14B C15B H15B 110.1(15) . . ?
C14B C15B C11B 104.4(2) . . ?
C15B C11B H11B 109.2(18) . . ?
C10B C11B C15B 110.5(2) . . ?
C10B C11B H11B 110.0(18) . . ?
C10B C11B C12B 114.1(2) . . ?
C12B C11B C15B 102.7(2) . . ?
C12B C11B H11B 110.1(18) . . ?
O5B C10B C11B 122.3(3) . . ?
O5B C10B C9B 121.2(3) . . ?
C9B C10B C11B 116.4(2) . . ?
C10B C9B H9BA 110.0(17) . . ?
C10B C9B H9BB 107.7(18) . . ?
C10B C9B C8B 112.9(2) . . ?
H9BA C9B H9BB 110(3) . . ?
C8B C9B H9BA 108.2(18) . . ?
C8B C9B H9BB 107.7(18) . . ?
C9B C8B H8B 111.1(17) . . ?
C9B C8B C3B 114.9(2) . . ?
C3B C8B H8B 106.2(17) . . ?
C7B C8B C9B 109.2(2) . . ?
C7B C8B H8B 104.4(17) . . ?
C7B C8B C3B 110.6(2) . . ?
C8B C3B H3B 109.2(16) . . ?
C2B C3B C8B 114.8(2) . . ?
C2B C3B H3B 107.6(16) . . ?
C2B C3B C4B 108.2(2) . . ?
C4B C3B C8B 109.5(2) . . ?
C4B C3B H3B 107.3(16) . . ?
C15B C2B H2B 105.6(18) . . ?
C3B C2B C15B 122.3(2) . . ?
C3B C2B H2B 107.1(17) . . ?
C1B C2B C15B 103.3(2) . . ?
C1B C2B C3B 115.5(2) . . ?
C1B C2B H2B 100.5(18) . . ?
O2B C1B O1B 120.5(2) . . ?
O2B C1B C2B 129.1(2) . . ?
O1B C1B C2B 110.4(2) . . ?
O1B C14B C15B 105.2(2) . . ?
O1B C14B H14B 107(2) . . ?
O1B C14B C13B 109.8(2) . . ?
C15B C14B H14B 111(2) . . ?
C13B C14B C15B 108.0(2) . . ?
C13B C14B H14B 115(2) . . ?
C14B C13B H13C 114.2(18) . . ?
C14B C13B H13D 109.1(16) . . ?
C14B C13B C12B 105.4(2) . . ?
H13C C13B H13D 108(2) . . ?
C12B C13B H13C 111.9(18) . . ?
C12B C13B H13D 108.0(15) . . ?
O4B C12B C11B 113.8(2) . . ?
O4B C12B C13B 112.7(2) . . ?
O4B C12B C19B 105.2(2) . . ?
C13B C12B C11B 103.9(2) . . ?
C19B C12B C11B 110.9(2) . . ?
C19B C12B C13B 110.4(2) . . ?
C12B C19B H19D 110(2) . . ?
C12B C19B H19E 114(2) . . ?
C12B C19B H19F 108.8(18) . . ?
H19D C19B H19E 109(3) . . ?
H19D C19B H19F 108(3) . . ?
H19E C19B H19F 108(3) . . ?
O3B C7B C8B 121.4(2) . . ?
O3B C7B C6B 122.2(3) . . ?
C6B C7B C8B 116.4(2) . . ?
C7B C6B H6BA 106.7(17) . . ?
C7B C6B H6BB 107.4(19) . . ?
C7B C6B C5B 112.8(2) . . ?
H6BA C6B H6BB 110(3) . . ?
C5B C6B H6BA 114.7(17) . . ?
C5B C6B H6BB 105.2(19) . . ?
C6B C5B H5B 106.9(19) . . ?
C4B C5B C6B 108.4(2) . . ?
C4B C5B H5B 108.1(19) . . ?
C16B C5B C6B 115.7(3) . . ?
C16B C5B H5B 105(2) . . ?
C16B C5B C4B 112.0(2) . . ?
C3B C4B H4BB 108.3(19) . . ?
C3B C4B H4BC 107.6(15) . . ?
C5B C4B C3B 113.4(2) . . ?
C5B C4B H4BB 109.7(18) . . ?
C5B C4B H4BC 109.8(15) . . ?
H4BB C4B H4BC 108(2) . . ?
C18B C16B C5B 124.3(3) . . ?
C18B C16B C17B 121.4(3) . . ?
C17B C16B C5B 114.2(3) . . ?
C16B C18B H18C 123(2) . . ?
C16B C18B H18D 124(2) . . ?
H18C C18B H18D 112(3) . . ?
C16B C17B H17D 111.6(18) . . ?
C16B C17B H17E 112(2) . . ?
C16B C17B H17F 110(2) . . ?
H17D C17B H17E 107(3) . . ?
H17D C17B H17F 112(3) . . ?
H17E C17B H17F 104(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O5 0.94(5) 2.11(5) 2.796(3) 129(4) .
C15 H15 O3 0.96(3) 2.52(3) 3.227(3) 131(2) 4_566
C8 H8 O2 0.94(3) 2.57(3) 3.228(3) 128(2) .
C2 H2 O2B 0.96(3) 2.50(3) 3.253(3) 136(2) .
C14 H14 O1B 0.97(3) 2.50(3) 3.450(3) 164(2) .
O4B H4BA O5B 0.90(4) 2.12(4) 2.863(3) 139(3) .
C15B H15B O2B 0.96(3) 2.39(3) 3.270(3) 151(2) 4_556
C8B H8B O2B 0.97(3) 2.57(3) 3.222(3) 125(2) .
C2B H2B O2 0.99(3) 2.62(3) 3.440(3) 140(2) 4_556
C2B H2B O1 0.99(3) 2.61(3) 3.588(3) 169(2) 4_556
C13B H13D O5B 1.02(3) 2.54(3) 3.049(3) 110.7(18) .
C6B H6BA O4B 1.00(3) 2.54(3) 3.449(4) 150(2) 2_664

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 C10 C9 C8 -86.1(3) . . . . ?
O1 C14 C13 C12 -115.2(2) . . . . ?
O3 C7 C6 C5 131.8(3) . . . . ?
C15 C11 C10 O5 89.7(3) . . . . ?
C15 C11 C10 C9 -86.3(3) . . . . ?
C15 C11 C12 O4 -155.9(2) . . . . ?
C15 C11 C12 C13 -33.5(3) . . . . ?
C15 C11 C12 C19 86.2(3) . . . . ?
C15 C2 C1 O2 162.0(3) . . . . ?
C15 C2 C1 O1 -19.2(3) . . . . ?
C15 C14 C13 C12 -1.6(3) . . . . ?
C11 C15 C2 C3 45.8(3) . . . . ?
C11 C15 C2 C1 -86.9(3) . . . . ?
C11 C15 C14 O1 97.4(2) . . . . ?
C11 C15 C14 C13 -19.1(3) . . . . ?
C11 C10 C9 C8 90.0(3) . . . . ?
C10 C11 C12 O4 -36.7(3) . . . . ?
C10 C11 C12 C13 85.7(3) . . . . ?
C10 C11 C12 C19 -154.5(3) . . . . ?
C10 C9 C8 C3 -58.9(3) . . . . ?
C10 C9 C8 C7 174.8(2) . . . . ?
C9 C8 C3 C2 61.9(3) . . . . ?
C9 C8 C3 C4 -175.0(2) . . . . ?
C9 C8 C7 O3 -5.7(4) . . . . ?
C9 C8 C7 C6 176.6(2) . . . . ?
C8 C3 C2 C15 -77.8(3) . . . . ?
C8 C3 C2 C1 49.4(3) . . . . ?
C8 C3 C4 C5 57.8(3) . . . . ?
C8 C7 C6 C5 -50.5(3) . . . . ?
C3 C8 C7 O3 -133.8(3) . . . . ?
C3 C8 C7 C6 48.5(3) . . . . ?
C3 C2 C1 O2 26.3(4) . . . . ?
C3 C2 C1 O1 -155.0(2) . . . . ?
C2 C15 C11 C10 23.1(3) . . . . ?
C2 C15 C11 C12 145.6(2) . . . . ?
C2 C15 C14 O1 -27.4(3) . . . . ?
C2 C15 C14 C13 -143.9(2) . . . . ?
C2 C3 C4 C5 -176.0(2) . . . . ?
C1 O1 C14 C15 16.8(3) . . . . ?
C1 O1 C14 C13 132.3(2) . . . . ?
C14 O1 C1 O2 -179.6(2) . . . . ?
C14 O1 C1 C2 1.5(3) . . . . ?
C14 C15 C11 C10 -90.2(3) . . . . ?
C14 C15 C11 C12 32.3(3) . . . . ?
C14 C15 C2 C3 160.3(2) . . . . ?
C14 C15 C2 C1 27.7(3) . . . . ?
C14 C13 C12 O4 145.3(2) . . . . ?
C14 C13 C12 C11 21.9(3) . . . . ?
C14 C13 C12 C19 -97.0(3) . . . . ?
C12 C11 C10 O5 -26.4(4) . . . . ?
C12 C11 C10 C9 157.6(2) . . . . ?
C7 C8 C3 C2 -173.2(2) . . . . ?
C7 C8 C3 C4 -50.1(3) . . . . ?
C7 C6 C5 C4 53.9(3) . . . . ?
C7 C6 C5 C16 -72.7(3) . . . . ?
C6 C5 C4 C3 -59.3(3) . . . . ?
C6 C5 C16 C18 0.8(4) . . . . ?
C6 C5 C16 C17 -177.1(2) . . . . ?
C4 C3 C2 C15 158.7(2) . . . . ?
C4 C3 C2 C1 -74.1(3) . . . . ?
C4 C5 C16 C18 -123.9(3) . . . . ?
C4 C5 C16 C17 58.2(3) . . . . ?
C16 C5 C4 C3 67.9(3) . . . . ?
O5B C10B C9B C8B -89.2(3) . . . . ?
O1B C14B C13B C12B -124.2(2) . . . . ?
O3B C7B C6B C5B 133.4(3) . . . . ?
C15B C11B C10B O5B 92.9(3) . . . . ?
C15B C11B C10B C9B -84.2(3) . . . . ?
C15B C11B C12B O4B -162.8(2) . . . . ?
C15B C11B C12B C13B -39.8(3) . . . . ?
C15B C11B C12B C19B 78.9(3) . . . . ?
C15B C2B C1B O2B 161.2(3) . . . . ?
C15B C2B C1B O1B -19.2(3) . . . . ?
C15B C14B C13B C12B -10.0(3) . . . . ?
C11B C15B C2B C3B 42.2(4) . . . . ?
C11B C15B C2B C1B -90.0(3) . . . . ?
C11B C15B C14B O1B 102.5(2) . . . . ?
C11B C15B C14B C13B -14.7(3) . . . . ?
C11B C10B C9B C8B 88.0(3) . . . . ?
C10B C11B C12B O4B -43.2(3) . . . . ?
C10B C11B C12B C13B 79.8(3) . . . . ?
C10B C11B C12B C19B -161.6(2) . . . . ?
C10B C9B C8B C3B -60.4(3) . . . . ?
C10B C9B C8B C7B 174.7(2) . . . . ?
C9B C8B C3B C2B 62.1(3) . . . . ?
C9B C8B C3B C4B -175.9(2) . . . . ?
C9B C8B C7B O3B -6.6(4) . . . . ?
C9B C8B C7B C6B 176.2(2) . . . . ?
C8B C3B C2B C15B -75.4(3) . . . . ?
C8B C3B C2B C1B 51.7(3) . . . . ?
C8B C3B C4B C5B 59.9(3) . . . . ?
C8B C7B C6B C5B -49.3(3) . . . . ?
C3B C8B C7B O3B -133.9(3) . . . . ?
C3B C8B C7B C6B 48.8(3) . . . . ?
C3B C2B C1B O2B 25.0(4) . . . . ?
C3B C2B C1B O1B -155.3(2) . . . . ?
C2B C15B C11B C10B 25.7(3) . . . . ?
C2B C15B C11B C12B 147.7(2) . . . . ?
C2B C15B C14B O1B -23.4(2) . . . . ?
C2B C15B C14B C13B -140.6(2) . . . . ?
C2B C3B C4B C5B -174.3(2) . . . . ?
C1B O1B C14B C15B 12.6(3) . . . . ?
C1B O1B C14B C13B 128.6(2) . . . . ?
C14B O1B C1B O2B -176.1(2) . . . . ?
C14B O1B C1B C2B 4.2(3) . . . . ?
C14B C15B C11B C10B -88.7(2) . . . . ?
C14B C15B C11B C12B 33.3(3) . . . . ?
C14B C15B C2B C3B 157.4(2) . . . . ?
C14B C15B C2B C1B 25.2(2) . . . . ?
C14B C13B C12B O4B 154.6(2) . . . . ?
C14B C13B C12B C11B 30.9(3) . . . . ?
C14B C13B C12B C19B -88.1(3) . . . . ?
C12B C11B C10B O5B -22.2(4) . . . . ?
C12B C11B C10B C9B 160.7(2) . . . . ?
C7B C8B C3B C2B -173.7(2) . . . . ?
C7B C8B C3B C4B -51.7(3) . . . . ?
C7B C6B C5B C4B 51.5(3) . . . . ?
C7B C6B C5B C16B -75.3(3) . . . . ?
C6B C5B C4B C3B -58.7(3) . . . . ?
C6B C5B C16B C18B 3.0(4) . . . . ?
C6B C5B C16B C17B -177.2(2) . . . . ?
C4B C3B C2B C15B 162.0(2) . . . . ?
C4B C3B C2B C1B -70.9(3) . . . . ?
C4B C5B C16B C18B -121.9(3) . . . . ?
C4B C5B C16B C17B 57.9(3) . . . . ?
C16B C5B C4B C3B 70.1(3) . . . . ?

_olex2_submission_original_sample_id RAC-XI-203
_olex2_submission_special_instructions 'No special instructions were received'
