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

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

data_151129_0m
_database_code_depnum_ccdc_archive 'CCDC 1455406'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H32 O8'
_chemical_formula_weight         592.61

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8910(9)
_cell_length_b                   16.2219(12)
_cell_length_c                   15.2941(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.262(4)
_cell_angle_gamma                90
_cell_volume                     2945.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2346
_cell_measurement_theta_min      2.4573
_cell_measurement_theta_max      21.2856

_exptl_crystal_description       Lump
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8722
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            25025
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6020
_reflns_number_gt                3433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6020
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1720
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.71367(13) 0.40491(9) 0.86760(11) 0.0600(5) Uani 1 1 d . . . . .
O2 O 0.87987(12) 0.03775(8) 0.90223(10) 0.0521(4) Uani 1 1 d . . . . .
O3 O 0.74298(12) -0.13128(9) 0.86917(10) 0.0567(4) Uani 1 1 d . . . . .
O4 O 0.56734(13) -0.10305(10) 0.88688(13) 0.0745(6) Uani 1 1 d . . . . .
O5 O 0.38117(11) 0.17744(8) 0.39220(10) 0.0486(4) Uani 1 1 d . . . . .
O6 O 0.21454(13) 0.54432(9) 0.35220(12) 0.0651(5) Uani 1 1 d . . . . .
O7 O 0.24229(13) 0.00864(9) 0.37329(11) 0.0573(5) Uani 1 1 d . . . . .
O8 O 0.06929(14) 0.03756(10) 0.39732(14) 0.0843(6) Uani 1 1 d . . . . .
C1 C 0.8014(2) 0.46083(13) 0.89431(18) 0.0672(7) Uani 1 1 d . . . . .
H3 H 0.8216 0.4530 0.9554 0.101 Uiso 1 1 calc R U . . .
H1 H 0.7758 0.5164 0.8847 0.101 Uiso 1 1 calc R U . . .
H16 H 0.8659 0.4508 0.8608 0.101 Uiso 1 1 calc R U . . .
C2 C 0.73553(18) 0.32283(12) 0.87438(13) 0.0450(5) Uani 1 1 d . . . . .
C3 C 0.65363(18) 0.27126(13) 0.83528(14) 0.0499(6) Uani 1 1 d . . . . .
H12 H 0.5899 0.2938 0.8065 0.060 Uiso 1 1 calc R U . . .
C4 C 0.66655(17) 0.18783(13) 0.83910(14) 0.0466(5) Uani 1 1 d . . . . .
H13 H 0.6115 0.1542 0.8122 0.056 Uiso 1 1 calc R U . . .
C5 C 0.76099(16) 0.15164(12) 0.88258(13) 0.0409(5) Uani 1 1 d . . . . .
C6 C 0.77193(17) 0.06162(12) 0.88878(13) 0.0412(5) Uani 1 1 d . . . . .
C7 C 0.90258(18) -0.04690(12) 0.92326(14) 0.0478(6) Uani 1 1 d . . . . .
H10 H 0.8709 -0.0595 0.9787 0.057 Uiso 1 1 calc R U . . .
H11 H 0.9835 -0.0545 0.9307 0.057 Uiso 1 1 calc R U . . .
C8 C 0.85594(17) -0.10695(12) 0.85519(13) 0.0431(5) Uani 1 1 d . . . . .
H9 H 0.8578 -0.0812 0.7973 0.052 Uiso 1 1 calc R U . . .
C9 C 0.92457(17) -0.18555(12) 0.85559(13) 0.0411(5) Uani 1 1 d . . . . .
C10 C 0.89419(19) -0.25451(13) 0.90175(14) 0.0515(6) Uani 1 1 d . . . . .
H8 H 0.8300 -0.2532 0.9338 0.062 Uiso 1 1 calc R U . . .
C11 C 0.9586(2) -0.32564(14) 0.90067(16) 0.0572(6) Uani 1 1 d . . . . .
H7 H 0.9374 -0.3718 0.9318 0.069 Uiso 1 1 calc R U . . .
C12 C 1.0535(2) -0.32813(14) 0.85392(16) 0.0568(6) Uani 1 1 d . . . . .
H2 H 1.0963 -0.3761 0.8529 0.068 Uiso 1 1 calc R U . . .
C13 C 0.83020(18) 0.28902(13) 0.91628(14) 0.0501(6) Uani 1 1 d . . . . .
H15 H 0.8859 0.3230 0.9417 0.060 Uiso 1 1 calc R U . . .
C14 C 0.84190(18) 0.20441(13) 0.92028(14) 0.0495(6) Uani 1 1 d . . . . .
H14 H 0.9058 0.1821 0.9491 0.059 Uiso 1 1 calc R U . . .
C15 C 0.66109(19) -0.07548(13) 0.88083(14) 0.0500(6) Uani 1 1 d . . . . .
C16 C 0.68080(18) 0.01227(13) 0.88286(14) 0.0476(6) Uani 1 1 d . . . . .
H4 H 0.6140 0.0422 0.8792 0.057 Uiso 1 1 calc R U . . .
C17 C 1.08518(19) -0.25976(14) 0.80858(15) 0.0558(6) Uani 1 1 d . . . . .
H5 H 1.1501 -0.2612 0.7774 0.067 Uiso 1 1 calc R U . . .
C18 C 1.02099(18) -0.18872(13) 0.80911(14) 0.0494(6) Uani 1 1 d . . . . .
H6 H 1.0428 -0.1427 0.7780 0.059 Uiso 1 1 calc R U . . .
C19 C 0.5492(2) -0.19236(15) 0.36518(17) 0.0629(7) Uani 1 1 d . . . . .
H17 H 0.5917 -0.2405 0.3667 0.075 Uiso 1 1 calc R U . . .
C20 C 0.4492(2) -0.18940(13) 0.40460(16) 0.0600(7) Uani 1 1 d . . . . .
H32 H 0.4238 -0.2359 0.4331 0.072 Uiso 1 1 calc R U . . .
C21 C 0.38520(19) -0.11821(13) 0.40267(14) 0.0496(6) Uani 1 1 d . . . . .
H31 H 0.3173 -0.1170 0.4299 0.060 Uiso 1 1 calc R U . . .
C22 C 0.42206(17) -0.04874(12) 0.36024(13) 0.0395(5) Uani 1 1 d . . . . .
C23 C 0.35591(17) 0.03077(12) 0.35631(13) 0.0416(5) Uani 1 1 d . . . . .
H28 H 0.3567 0.0530 0.2968 0.050 Uiso 1 1 calc R U . . .
C24 C 0.40439(18) 0.09443(11) 0.41947(14) 0.0461(6) Uani 1 1 d . . . . .
H20 H 0.3739 0.0856 0.4762 0.055 Uiso 1 1 calc R U . . .
H19 H 0.4853 0.0869 0.4263 0.055 Uiso 1 1 calc R U . . .
C25 C 0.27290(17) 0.20155(12) 0.38377(12) 0.0399(5) Uani 1 1 d . . . . .
C26 C 0.26215(16) 0.29188(12) 0.37397(12) 0.0400(5) Uani 1 1 d . . . . .
C27 C 0.16516(18) 0.32699(12) 0.33410(14) 0.0479(6) Uani 1 1 d . . . . .
H26 H 0.1078 0.2928 0.3117 0.057 Uiso 1 1 calc R U . . .
C28 C 0.15248(18) 0.41053(13) 0.32724(14) 0.0502(6) Uani 1 1 d . . . . .
H25 H 0.0869 0.4325 0.3006 0.060 Uiso 1 1 calc R U . . .
C29 C 0.23742(18) 0.46255(12) 0.35995(14) 0.0459(5) Uani 1 1 d . . . . .
C30 C 0.3016(2) 0.60177(13) 0.37518(17) 0.0639(7) Uani 1 1 d . . . . .
H18 H 0.3255 0.5949 0.4357 0.096 Uiso 1 1 calc R U . . .
H21 H 0.2738 0.6568 0.3658 0.096 Uiso 1 1 calc R U . . .
H22 H 0.3642 0.5924 0.3395 0.096 Uiso 1 1 calc R U . . .
C31 C 0.1621(2) 0.06496(14) 0.38667(15) 0.0511(6) Uani 1 1 d . . . . .
C32 C 0.18130(18) 0.15265(12) 0.38544(14) 0.0456(5) Uani 1 1 d . . . . .
H27 H 0.1147 0.1827 0.3859 0.055 Uiso 1 1 calc R U . . .
C33 C 0.33555(18) 0.42963(12) 0.39762(14) 0.0457(5) Uani 1 1 d . . . . .
H24 H 0.3936 0.4642 0.4182 0.055 Uiso 1 1 calc R U . . .
C34 C 0.34740(17) 0.34487(12) 0.40468(13) 0.0450(5) Uani 1 1 d . . . . .
H23 H 0.4136 0.3230 0.4304 0.054 Uiso 1 1 calc R U . . .
C35 C 0.52372(19) -0.05248(13) 0.32046(14) 0.0489(6) Uani 1 1 d . . . . .
H30 H 0.5496 -0.0064 0.2916 0.059 Uiso 1 1 calc R U . . .
C36 C 0.5868(2) -0.12366(15) 0.32324(16) 0.0593(7) Uani 1 1 d . . . . .
H29 H 0.6551 -0.1252 0.2966 0.071 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 C2 1.359(2) . ?
O1 C1 1.424(2) . ?
O2 C6 1.345(2) . ?
O2 C7 1.433(2) . ?
O3 C15 1.349(2) . ?
O3 C8 1.428(2) . ?
O4 C15 1.210(2) . ?
O5 C25 1.345(2) . ?
O5 C24 1.432(2) . ?
O6 C29 1.358(2) . ?
O6 C30 1.422(2) . ?
O7 C31 1.345(3) . ?
O7 C23 1.436(2) . ?
O8 C31 1.210(2) . ?
C1 H3 0.9600 . ?
C1 H1 0.9600 . ?
C1 H16 0.9600 . ?
C2 C13 1.377(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.363(3) . ?
C3 H12 0.9300 . ?
C4 C5 1.401(3) . ?
C4 H13 0.9300 . ?
C5 C14 1.388(3) . ?
C5 C6 1.469(3) . ?
C6 C16 1.346(3) . ?
C7 C8 1.508(3) . ?
C7 H10 0.9700 . ?
C7 H11 0.9700 . ?
C8 C9 1.514(3) . ?
C8 H9 0.9800 . ?
C9 C10 1.382(3) . ?
C9 C18 1.384(3) . ?
C10 C11 1.386(3) . ?
C10 H8 0.9300 . ?
C11 C12 1.370(3) . ?
C11 H7 0.9300 . ?
C12 C17 1.372(3) . ?
C12 H2 0.9300 . ?
C13 C14 1.381(3) . ?
C13 H15 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.443(3) . ?
C16 H4 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H5 0.9300 . ?
C18 H6 0.9300 . ?
C19 C20 1.365(3) . ?
C19 C36 1.373(3) . ?
C19 H17 0.9300 . ?
C20 C21 1.383(3) . ?
C20 H32 0.9300 . ?
C21 C22 1.384(3) . ?
C21 H31 0.9300 . ?
C22 C35 1.385(3) . ?
C22 C23 1.510(3) . ?
C23 C24 1.506(3) . ?
C23 H28 0.9800 . ?
C24 H20 0.9700 . ?
C24 H19 0.9700 . ?
C25 C32 1.349(3) . ?
C25 C26 1.478(3) . ?
C26 C34 1.390(3) . ?
C26 C27 1.395(3) . ?
C27 C28 1.367(3) . ?
C27 H26 0.9300 . ?
C28 C29 1.388(3) . ?
C28 H25 0.9300 . ?
C29 C33 1.379(3) . ?
C30 H18 0.9600 . ?
C30 H21 0.9600 . ?
C30 H22 0.9600 . ?
C31 C32 1.441(3) . ?
C32 H27 0.9300 . ?
C33 C34 1.386(3) . ?
C33 H24 0.9300 . ?
C34 H23 0.9300 . ?
C35 C36 1.376(3) . ?
C35 H30 0.9300 . ?
C36 H29 0.9300 . ?

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
C2 O1 C1 117.91(17) . . ?
C6 O2 C7 118.44(16) . . ?
C15 O3 C8 121.79(16) . . ?
C25 O5 C24 117.99(16) . . ?
C29 O6 C30 118.65(17) . . ?
C31 O7 C23 122.70(16) . . ?
O1 C1 H3 109.5 . . ?
O1 C1 H1 109.5 . . ?
H3 C1 H1 109.5 . . ?
O1 C1 H16 109.5 . . ?
H3 C1 H16 109.5 . . ?
H1 C1 H16 109.5 . . ?
O1 C2 C13 124.98(19) . . ?
O1 C2 C3 115.44(18) . . ?
C13 C2 C3 119.59(19) . . ?
C4 C3 C2 120.24(19) . . ?
C4 C3 H12 119.9 . . ?
C2 C3 H12 119.9 . . ?
C3 C4 C5 121.46(19) . . ?
C3 C4 H13 119.3 . . ?
C5 C4 H13 119.3 . . ?
C14 C5 C4 117.16(18) . . ?
C14 C5 C6 121.97(18) . . ?
C4 C5 C6 120.87(17) . . ?
O2 C6 C16 126.61(19) . . ?
O2 C6 C5 112.11(17) . . ?
C16 C6 C5 121.26(18) . . ?
O2 C7 C8 114.01(16) . . ?
O2 C7 H10 108.7 . . ?
C8 C7 H10 108.7 . . ?
O2 C7 H11 108.7 . . ?
C8 C7 H11 108.7 . . ?
H10 C7 H11 107.6 . . ?
O3 C8 C7 112.78(18) . . ?
O3 C8 C9 106.15(16) . . ?
C7 C8 C9 111.36(16) . . ?
O3 C8 H9 108.8 . . ?
C7 C8 H9 108.8 . . ?
C9 C8 H9 108.8 . . ?
C10 C9 C18 118.7(2) . . ?
C10 C9 C8 121.8(2) . . ?
C18 C9 C8 119.44(19) . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H8 119.8 . . ?
C11 C10 H8 119.8 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H7 119.9 . . ?
C10 C11 H7 119.9 . . ?
C11 C12 C17 119.9(2) . . ?
C11 C12 H2 120.1 . . ?
C17 C12 H2 120.1 . . ?
C2 C13 C14 119.61(19) . . ?
C2 C13 H15 120.2 . . ?
C14 C13 H15 120.2 . . ?
C13 C14 C5 121.93(19) . . ?
C13 C14 H14 119.0 . . ?
C5 C14 H14 119.0 . . ?
O4 C15 O3 115.9(2) . . ?
O4 C15 C16 120.8(2) . . ?
O3 C15 C16 123.2(2) . . ?
C6 C16 C15 135.8(2) . . ?
C6 C16 H4 112.1 . . ?
C15 C16 H4 112.1 . . ?
C12 C17 C18 120.2(2) . . ?
C12 C17 H5 119.9 . . ?
C18 C17 H5 119.9 . . ?
C17 C18 C9 120.5(2) . . ?
C17 C18 H6 119.7 . . ?
C9 C18 H6 119.7 . . ?
C20 C19 C36 119.5(2) . . ?
C20 C19 H17 120.2 . . ?
C36 C19 H17 120.2 . . ?
C19 C20 C21 120.8(2) . . ?
C19 C20 H32 119.6 . . ?
C21 C20 H32 119.6 . . ?
C20 C21 C22 120.1(2) . . ?
C20 C21 H31 119.9 . . ?
C22 C21 H31 119.9 . . ?
C21 C22 C35 118.54(19) . . ?
C21 C22 C23 122.4(2) . . ?
C35 C22 C23 119.05(19) . . ?
O7 C23 C24 112.66(18) . . ?
O7 C23 C22 105.82(16) . . ?
C24 C23 C22 112.37(16) . . ?
O7 C23 H28 108.6 . . ?
C24 C23 H28 108.6 . . ?
C22 C23 H28 108.6 . . ?
O5 C24 C23 113.43(16) . . ?
O5 C24 H20 108.9 . . ?
C23 C24 H20 108.9 . . ?
O5 C24 H19 108.9 . . ?
C23 C24 H19 108.9 . . ?
H20 C24 H19 107.7 . . ?
O5 C25 C32 126.64(18) . . ?
O5 C25 C26 112.03(17) . . ?
C32 C25 C26 121.32(18) . . ?
C34 C26 C27 117.64(18) . . ?
C34 C26 C25 121.44(17) . . ?
C27 C26 C25 120.92(17) . . ?
C28 C27 C26 121.55(19) . . ?
C28 C27 H26 119.2 . . ?
C26 C27 H26 119.2 . . ?
C27 C28 C29 120.03(19) . . ?
C27 C28 H25 120.0 . . ?
C29 C28 H25 120.0 . . ?
O6 C29 C33 125.12(19) . . ?
O6 C29 C28 115.13(18) . . ?
C33 C29 C28 119.75(18) . . ?
O6 C30 H18 109.5 . . ?
O6 C30 H21 109.5 . . ?
H18 C30 H21 109.5 . . ?
O6 C30 H22 109.5 . . ?
H18 C30 H22 109.5 . . ?
H21 C30 H22 109.5 . . ?
O8 C31 O7 115.5(2) . . ?
O8 C31 C32 120.7(2) . . ?
O7 C31 C32 123.7(2) . . ?
C25 C32 C31 135.2(2) . . ?
C25 C32 H27 112.4 . . ?
C31 C32 H27 112.4 . . ?
C29 C33 C34 119.78(19) . . ?
C29 C33 H24 120.1 . . ?
C34 C33 H24 120.1 . . ?
C33 C34 C26 121.21(19) . . ?
C33 C34 H23 119.4 . . ?
C26 C34 H23 119.4 . . ?
C36 C35 C22 120.7(2) . . ?
C36 C35 H30 119.6 . . ?
C22 C35 H30 119.6 . . ?
C19 C36 C35 120.3(2) . . ?
C19 C36 H29 119.9 . . ?
C35 C36 H29 119.9 . . ?

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

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

data_mo_160219_0m
_database_code_depnum_ccdc_archive 'CCDC 1459007'
_audit_update_record             
;
2016-03-08 deposited with the CCDC.
2016-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.7294(5)
_cell_length_b                   16.4971(16)
_cell_length_c                   16.9275(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.391(2)
_cell_angle_gamma                90
_cell_volume                     1590.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    1597
_cell_measurement_theta_min      2.4692
_cell_measurement_theta_max      23.3395

_exptl_crystal_description       Lump
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8614
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            13264
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         26.406
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3257
_reflns_number_gt                1930
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.2427P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.4797(2) 0.07470(8) 0.30921(8) 0.0519(4) Uani 1 1 d . . . . .
O2 O 0.8925(3) -0.27014(10) 0.37020(10) 0.0731(5) Uani 1 1 d . . . . .
O3 O 0.1514(2) 0.18814(8) 0.40122(8) 0.0457(4) Uani 1 1 d . . . . .
O4 O -0.0955(2) 0.10857(9) 0.45199(10) 0.0586(4) Uani 1 1 d . . . . .
C1 C 0.5062(5) 0.45454(15) 0.37413(17) 0.0763(8) Uani 1 1 d . . . . .
H1 H 0.5346 0.5101 0.3744 0.092 Uiso 1 1 calc R U . . .
C2 C 0.2929(4) 0.42509(14) 0.34262(15) 0.0659(7) Uani 1 1 d . . . . .
H18 H 0.1764 0.4605 0.3212 0.079 Uiso 1 1 calc R U . . .
C3 C 0.2508(4) 0.34305(13) 0.34272(13) 0.0544(6) Uani 1 1 d . . . . .
H17 H 0.1052 0.3234 0.3213 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4224(3) 0.28924(12) 0.37426(12) 0.0438(5) Uani 1 1 d . . . . .
C5 C 0.3821(3) 0.19915(12) 0.37666(11) 0.0409(5) Uani 1 1 d . . . . .
H14 H 0.4978 0.1754 0.4171 0.049 Uiso 1 1 calc R U . . .
C6 C 0.4030(4) 0.15739(12) 0.29782(12) 0.0467(5) Uani 1 1 d . . . . .
H3 H 0.5269 0.1858 0.2734 0.056 Uiso 1 1 calc R U . . .
C7 C 0.3994(3) 0.02649(11) 0.36455(11) 0.0392(5) Uani 1 1 d . . . . .
C8 C 0.5205(3) -0.05323(11) 0.36541(11) 0.0383(5) Uani 1 1 d . . . . .
C9 C 0.4475(3) -0.11916(12) 0.40726(12) 0.0462(5) Uani 1 1 d . . . . .
H12 H 0.3151 -0.1140 0.4341 0.055 Uiso 1 1 calc R U . . .
C10 C 0.5657(4) -0.19194(12) 0.41008(12) 0.0484(5) Uani 1 1 d . . . . .
H11 H 0.5135 -0.2351 0.4387 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7614(4) -0.20066(13) 0.37042(13) 0.0490(5) Uani 1 1 d . . . . .
C12 C 0.8475(5) -0.33224(16) 0.42345(17) 0.0842(8) Uani 1 1 d . . . . .
H7 H 0.8629 -0.3112 0.4767 0.126 Uiso 1 1 calc R U . . .
H8 H 0.9580 -0.3755 0.4200 0.126 Uiso 1 1 calc R U . . .
H2 H 0.6909 -0.3524 0.4100 0.126 Uiso 1 1 calc R U . . .
C13 C 0.0882(3) 0.11299(12) 0.42305(12) 0.0422(5) Uani 1 1 d . . . . .
C14 C 0.2355(3) 0.04324(12) 0.41317(12) 0.0425(5) Uani 1 1 d . . . . .
H13 H 0.2116 0.0010 0.4478 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1870(4) 0.15993(15) 0.23853(14) 0.0693(7) Uani 1 1 d . . . . .
H5 H 0.2189 0.1335 0.1904 0.104 Uiso 1 1 calc R U . . .
H4 H 0.1438 0.2153 0.2273 0.104 Uiso 1 1 calc R U . . .
H6 H 0.0604 0.1326 0.2601 0.104 Uiso 1 1 calc R U . . .
C16 C 0.8341(4) -0.13683(13) 0.32708(14) 0.0568(6) Uani 1 1 d . . . . .
H10 H 0.9641 -0.1428 0.2992 0.068 Uiso 1 1 calc R U . . .
C17 C 0.7160(3) -0.06436(13) 0.32468(13) 0.0505(6) Uani 1 1 d . . . . .
H9 H 0.7678 -0.0217 0.2952 0.061 Uiso 1 1 calc R U . . .
C18 C 0.6377(4) 0.31995(14) 0.40516(14) 0.0609(6) Uani 1 1 d . . . . .
H16 H 0.7559 0.2849 0.4260 0.073 Uiso 1 1 calc R U . . .
C19 C 0.6782(4) 0.40225(15) 0.40532(18) 0.0787(8) Uani 1 1 d . . . . .
H15 H 0.8232 0.4225 0.4267 0.094 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 C7 1.348(2) . ?
O1 C6 1.439(2) . ?
O2 C11 1.371(2) . ?
O2 C12 1.407(3) . ?
O3 C13 1.354(2) . ?
O3 C5 1.441(2) . ?
O4 C13 1.212(2) . ?
C1 C2 1.367(3) . ?
C1 C19 1.370(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H18 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H17 0.9300 . ?
C4 C18 1.381(3) . ?
C4 C5 1.505(3) . ?
C5 C6 1.518(3) . ?
C5 H14 0.9800 . ?
C6 C15 1.505(3) . ?
C6 H3 0.9800 . ?
C7 C14 1.344(2) . ?
C7 C8 1.486(3) . ?
C8 C9 1.388(3) . ?
C8 C17 1.391(3) . ?
C9 C10 1.377(3) . ?
C9 H12 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H11 0.9300 . ?
C11 C16 1.374(3) . ?
C12 H7 0.9600 . ?
C12 H8 0.9600 . ?
C12 H2 0.9600 . ?
C13 C14 1.448(3) . ?
C14 H13 0.9300 . ?
C15 H5 0.9600 . ?
C15 H4 0.9600 . ?
C15 H6 0.9600 . ?
C16 C17 1.372(3) . ?
C16 H10 0.9300 . ?
C17 H9 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H16 0.9300 . ?
C19 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C6 121.97(15) . . ?
C11 O2 C12 117.86(19) . . ?
C13 O3 C5 118.42(14) . . ?
C2 C1 C19 120.0(2) . . ?
C2 C1 H1 120.0 . . ?
C19 C1 H1 120.0 . . ?
C1 C2 C3 119.9(2) . . ?
C1 C2 H18 120.0 . . ?
C3 C2 H18 120.0 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H17 119.5 . . ?
C4 C3 H17 119.5 . . ?
C18 C4 C3 118.4(2) . . ?
C18 C4 C5 119.01(18) . . ?
C3 C4 C5 122.56(18) . . ?
O3 C5 C4 106.29(14) . . ?
O3 C5 C6 111.17(15) . . ?
C4 C5 C6 113.39(16) . . ?
O3 C5 H14 108.6 . . ?
C4 C5 H14 108.6 . . ?
C6 C5 H14 108.6 . . ?
O1 C6 C15 109.38(17) . . ?
O1 C6 C5 111.41(16) . . ?
C15 C6 C5 115.71(17) . . ?
O1 C6 H3 106.6 . . ?
C15 C6 H3 106.6 . . ?
C5 C6 H3 106.6 . . ?
C14 C7 O1 128.30(18) . . ?
C14 C7 C8 122.22(17) . . ?
O1 C7 C8 109.49(15) . . ?
C9 C8 C17 117.05(18) . . ?
C9 C8 C7 122.09(17) . . ?
C17 C8 C7 120.85(18) . . ?
C10 C9 C8 121.72(18) . . ?
C10 C9 H12 119.1 . . ?
C8 C9 H12 119.1 . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H11 120.1 . . ?
C9 C10 H11 120.1 . . ?
O2 C11 C16 116.13(19) . . ?
O2 C11 C10 124.4(2) . . ?
C16 C11 C10 119.47(19) . . ?
O2 C12 H7 109.5 . . ?
O2 C12 H8 109.5 . . ?
H7 C12 H8 109.5 . . ?
O2 C12 H2 109.5 . . ?
H7 C12 H2 109.5 . . ?
H8 C12 H2 109.5 . . ?
O4 C13 O3 115.85(17) . . ?
O4 C13 C14 122.86(18) . . ?
O3 C13 C14 121.28(16) . . ?
C7 C14 C13 133.62(19) . . ?
C7 C14 H13 113.2 . . ?
C13 C14 H13 113.2 . . ?
C6 C15 H5 109.5 . . ?
C6 C15 H4 109.5 . . ?
H5 C15 H4 109.5 . . ?
C6 C15 H6 109.5 . . ?
H5 C15 H6 109.5 . . ?
H4 C15 H6 109.5 . . ?
C17 C16 C11 120.4(2) . . ?
C17 C16 H10 119.8 . . ?
C11 C16 H10 119.8 . . ?
C16 C17 C8 121.5(2) . . ?
C16 C17 H9 119.3 . . ?
C8 C17 H9 119.3 . . ?
C19 C18 C4 120.4(2) . . ?
C19 C18 H16 119.8 . . ?
C4 C18 H16 119.8 . . ?
C1 C19 C18 120.4(2) . . ?
C1 C19 H15 119.8 . . ?
C18 C19 H15 119.8 . . ?

_refine_diff_density_max         0.119
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035

_shelxl_version_number           2014/6

