# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_dm15220_0m
_database_code_depnum_ccdc_archive 'CCDC 1816205'
loop_
_audit_author_name
_audit_author_address
'quaternary isotetronic acid'
'457 zhongshan road, Dalian institute of chemical physics'
_audit_update_record             
;
2018-01-11 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 Br O5'
_chemical_formula_weight         397.26

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

_cell_length_a                   6.3224(5)
_cell_length_b                   11.8122(10)
_cell_length_c                   24.672(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1842.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    4442
_cell_measurement_theta_min      4.774
_cell_measurement_theta_max      50.778

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    2.254
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5948
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(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 ?
_diffrn_reflns_number            13332
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.911
_diffrn_reflns_theta_max         25.997
_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             3623
_reflns_number_gt                3276
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0274P)²+1.0500P] 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_abs_structure_details 
; 
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.010(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3623
_refine_ls_number_parameters     312
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
Br1 Br 0.69505(8) 1.53180(4) 0.06823(2) 0.04424(15) Uani 1 1 d . . . . .
O1 O -0.3514(7) 0.9126(4) 0.0365(2) 0.0279(10) Uani 0.6 1 d . . P A 1
O2 O -0.1638(9) 0.9639(5) 0.1107(2) 0.0268(12) Uani 0.6 1 d . . P A 1
O3 O -0.0519(9) 0.7351(4) 0.0217(2) 0.0364(13) Uani 0.6 1 d . . P A 1
H3 H -0.1622 0.7467 0.0036 0.055 Uiso 0.6 1 calc R U P A 1
O4 O -0.1718(10) 0.9538(7) 0.2130(3) 0.0367(15) Uani 0.65 1 d . . P A 1
O5 O 0.1186(9) 0.8421(5) 0.2191(2) 0.0567(16) Uani 0.65 1 d . . P A 1
O1' O -0.165(2) 0.7993(11) 0.0152(4) 0.071(3) Uani 0.4 1 d . . P A 2
O2' O -0.1355(17) 0.9356(10) 0.0820(5) 0.042(3) Uani 0.4 1 d . . P A 2
O3' O 0.1623(14) 0.6757(7) 0.0721(4) 0.053(2) Uani 0.4 1 d . . P A 2
H3' H 0.0980 0.6507 0.0448 0.080 Uiso 0.4 1 calc R U P A 2
O4' O -0.072(2) 0.9682(12) 0.2202(5) 0.034(3) Uani 0.35 1 d . . P A 2
O5' O -0.3207(19) 0.8886(12) 0.1709(4) 0.072(3) Uani 0.35 1 d . . P A 2
C1 C -0.2051(13) 0.8968(6) 0.0651(4) 0.0251(16) Uani 0.6 1 d . U P A 1
C2 C -0.0388(18) 0.8106(8) 0.0608(6) 0.027(2) Uani 0.6 1 d . U P A 1
C3 C 0.1077(13) 0.8273(8) 0.1003(5) 0.030(2) Uani 0.6 1 d . U P A 1
C4 C 0.0246(7) 0.9336(4) 0.13184(18) 0.0353(10) Uani 1 1 d . . . . .
C5 C 0.1633(10) 1.0398(5) 0.13077(19) 0.0606(16) Uani 1 1 d . . . . .
H5A H 0.0836 1.1036 0.1469 0.073 Uiso 1 1 calc R U . . .
H5B H 0.2901 1.0266 0.1534 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2325(7) 1.0724(3) 0.07470(17) 0.0381(10) Uani 1 1 d . . . . .
H6A H 0.1072 1.0759 0.0507 0.046 Uiso 1 1 calc R U . . .
H6B H 0.3288 1.0135 0.0603 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3447(6) 1.1858(3) 0.07390(18) 0.0331(9) Uani 1 1 d . . . . .
C8 C 0.2489(6) 1.2801(4) 0.05164(17) 0.0339(10) Uani 1 1 d . . . . .
H8 H 0.1116 1.2736 0.0363 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3501(6) 1.3839(4) 0.05135(17) 0.0344(10) Uani 1 1 d . . . . .
H9 H 0.2815 1.4489 0.0371 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5499(6) 1.3917(3) 0.0719(2) 0.0341(9) Uani 1 1 d . . . . .
C11 C 0.6506(7) 1.2989(4) 0.0938(2) 0.0401(11) Uani 1 1 d . . . . .
H11 H 0.7899 1.3056 0.1079 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5471(7) 1.1967(4) 0.0949(2) 0.0391(11) Uani 1 1 d . . . . .
H12 H 0.6150 1.1327 0.1104 0.047 Uiso 1 1 calc R U . . .
C13 C -0.0021(10) 0.9006(6) 0.1941(3) 0.0321(15) Uani 0.65 1 d . . P A 1
C14 C -0.2111(9) 0.9520(5) 0.27208(18) 0.0496(12) Uani 1 1 d . . . . .
C15 C -0.4103(9) 1.0209(6) 0.2729(2) 0.0635(16) Uani 1 1 d . . . . .
H15A H -0.3828 1.0955 0.2570 0.095 Uiso 1 1 calc R U . . .
H15B H -0.4581 1.0303 0.3104 0.095 Uiso 1 1 calc R U . . .
H15C H -0.5201 0.9821 0.2519 0.095 Uiso 1 1 calc R U . . .
C16 C -0.0454(9) 1.0058(6) 0.3069(2) 0.0693(19) Uani 1 1 d . . . . .
H16A H 0.0825 0.9589 0.3066 0.104 Uiso 1 1 calc R U . . .
H16B H -0.0982 1.0124 0.3441 0.104 Uiso 1 1 calc R U . . .
H16C H -0.0119 1.0812 0.2928 0.104 Uiso 1 1 calc R U . . .
C17 C -0.2554(15) 0.8301(5) 0.2869(3) 0.092(3) Uani 1 1 d . . . . .
H17A H -0.3546 0.7975 0.2607 0.138 Uiso 1 1 calc R U . . .
H17B H -0.3172 0.8267 0.3233 0.138 Uiso 1 1 calc R U . . .
H17C H -0.1229 0.7870 0.2863 0.138 Uiso 1 1 calc R U . . .
C18 C 0.3059(12) 0.7660(6) 0.1110(3) 0.0414(17) Uani 0.6 1 d . U P A 1
H18A H 0.3278 0.7087 0.0828 0.062 Uiso 0.6 1 calc R U P A 1
H18B H 0.2975 0.7291 0.1465 0.062 Uiso 0.6 1 calc R U P A 1
H18C H 0.4244 0.8195 0.1107 0.062 Uiso 0.6 1 calc R U P A 1
C1' C -0.081(3) 0.8381(16) 0.0574(8) 0.037(4) Uani 0.4 1 d . U P A 2
C2' C 0.083(3) 0.7827(12) 0.0854(6) 0.037(3) Uani 0.4 1 d . U P A 2
C3' C 0.142(3) 0.8448(13) 0.1238(6) 0.037(3) Uani 0.4 1 d . U P A 2
C13' C -0.151(2) 0.9317(10) 0.1777(7) 0.033(3) Uani 0.35 1 d . . P A 2
C18' C 0.321(2) 0.8244(10) 0.1663(5) 0.050(3) Uani 0.4 1 d . U P A 2
H18D H 0.4037 0.7579 0.1557 0.075 Uiso 0.4 1 calc R U P A 2
H18E H 0.2576 0.8117 0.2020 0.075 Uiso 0.4 1 calc R U P A 2
H18F H 0.4134 0.8909 0.1677 0.075 Uiso 0.4 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.895(4) . ?
O1 C1 1.179(10) . ?
O2 C4 1.349(7) . ?
O2 C1 1.401(10) . ?
O3 C2 1.315(16) . ?
O3 H3 0.8400 . ?
O4 C13 1.328(10) . ?
O4 C14 1.479(9) . ?
O5 C13 1.200(8) . ?
O1' C1' 1.26(2) . ?
O2' C1' 1.35(2) . ?
O2' C4 1.592(11) . ?
O3' C2' 1.399(17) . ?
O3' H3' 0.8400 . ?
O4' C13' 1.24(2) . ?
O4' C14 1.564(13) . ?
O5' C13' 1.197(17) . ?
C1 C2 1.467(10) . ?
C2 C3 1.358(19) . ?
C3 C18 1.471(11) . ?
C3 C4 1.569(11) . ?
C4 C3' 1.301(17) . ?
C4 C5 1.531(6) . ?
C4 C13' 1.587(17) . ?
C4 C13 1.594(8) . ?
C5 C6 1.501(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.516(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.382(6) . ?
C7 C12 1.387(6) . ?
C8 C9 1.383(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.363(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.378(6) . ?
C11 C12 1.374(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C16 1.497(8) . ?
C14 C15 1.500(8) . ?
C14 C17 1.512(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C1' C2' 1.41(2) . ?
C2' C3' 1.255(19) . ?
C3' C18' 1.56(2) . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 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
C4 O2 C1 108.9(6) . . ?
C2 O3 H3 109.5 . . ?
C13 O4 C14 118.4(7) . . ?
C1' O2' C4 100.0(11) . . ?
C2' O3' H3' 109.5 . . ?
C13' O4' C14 115.1(13) . . ?
O1 C1 O2 122.5(6) . . ?
O1 C1 C2 129.0(10) . . ?
O2 C1 C2 108.5(9) . . ?
O3 C2 C3 131.8(10) . . ?
O3 C2 C1 118.6(12) . . ?
C3 C2 C1 109.6(10) . . ?
C2 C3 C18 129.7(10) . . ?
C2 C3 C4 104.1(7) . . ?
C18 C3 C4 126.1(9) . . ?
C3' C4 C5 109.3(8) . . ?
O2 C4 C5 106.3(5) . . ?
O2 C4 C3 108.4(5) . . ?
C5 C4 C3 117.1(5) . . ?
C3' C4 C13' 119.8(8) . . ?
C5 C4 C13' 115.2(6) . . ?
C3' C4 O2' 105.0(8) . . ?
C5 C4 O2' 109.8(5) . . ?
C13' C4 O2' 96.0(7) . . ?
O2 C4 C13 110.1(4) . . ?
C5 C4 C13 106.1(4) . . ?
C3 C4 C13 108.6(5) . . ?
C6 C5 C4 113.1(4) . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 112.0(4) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C12 118.6(4) . . ?
C8 C7 C6 120.8(4) . . ?
C12 C7 C6 120.6(4) . . ?
C7 C8 C9 120.9(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 121.4(4) . . ?
C9 C10 Br1 119.3(3) . . ?
C11 C10 Br1 119.3(3) . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C7 120.9(4) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
O5 C13 O4 127.3(8) . . ?
O5 C13 C4 124.7(6) . . ?
O4 C13 C4 107.9(6) . . ?
O4 C14 C16 116.2(5) . . ?
O4 C14 C15 98.5(4) . . ?
C16 C14 C15 110.4(5) . . ?
O4 C14 C17 106.4(5) . . ?
C16 C14 C17 113.3(6) . . ?
C15 C14 C17 111.0(6) . . ?
C16 C14 O4' 91.5(6) . . ?
C15 C14 O4' 114.5(6) . . ?
C17 C14 O4' 114.7(7) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1' C1' O2' 125.4(18) . . ?
O1' C1' C2' 123.3(18) . . ?
O2' C1' C2' 111.3(16) . . ?
C3' C2' O3' 126.9(17) . . ?
C3' C2' C1' 108.5(18) . . ?
O3' C2' C1' 124.6(15) . . ?
C2' C3' C4 114.6(16) . . ?
C2' C3' C18' 129.2(16) . . ?
C4 C3' C18' 115.9(11) . . ?
O5' C13' O4' 128.8(18) . . ?
O5' C13' C4 122.3(14) . . ?
O4' C13' C4 108.4(11) . . ?
C3' C18' H18D 109.5 . . ?
C3' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C3' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 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
C4 O2 C1 O1 -173.4(6) . . . . ?
C4 O2 C1 C2 5.9(8) . . . . ?
O1 C1 C2 O3 -3.5(14) . . . . ?
O2 C1 C2 O3 177.3(8) . . . . ?
O1 C1 C2 C3 175.8(8) . . . . ?
O2 C1 C2 C3 -3.4(11) . . . . ?
O3 C2 C3 C18 2(2) . . . . ?
C1 C2 C3 C18 -177.3(8) . . . . ?
O3 C2 C3 C4 179.1(10) . . . . ?
C1 C2 C3 C4 -0.1(10) . . . . ?
C1 O2 C4 C3' -14.9(11) . . . . ?
C1 O2 C4 C5 120.9(5) . . . . ?
C1 O2 C4 C3 -5.9(7) . . . . ?
C1 O2 C4 C13' -127.7(7) . . . . ?
C1 O2 C4 O2' 19.5(9) . . . . ?
C1 O2 C4 C13 -124.6(5) . . . . ?
C2 C3 C4 C3' 167(2) . . . . ?
C18 C3 C4 C3' -15.6(17) . . . . ?
C2 C3 C4 O2 3.7(9) . . . . ?
C18 C3 C4 O2 -178.9(7) . . . . ?
C2 C3 C4 C5 -116.5(7) . . . . ?
C18 C3 C4 C5 60.8(10) . . . . ?
C2 C3 C4 C13' 82.1(11) . . . . ?
C18 C3 C4 C13' -100.6(10) . . . . ?
C2 C3 C4 O2' -8.9(8) . . . . ?
C18 C3 C4 O2' 168.4(9) . . . . ?
C2 C3 C4 C13 123.4(8) . . . . ?
C18 C3 C4 C13 -59.3(9) . . . . ?
C1' O2' C4 C3' 4.5(13) . . . . ?
C1' O2' C4 O2 -149.5(17) . . . . ?
C1' O2' C4 C5 121.8(11) . . . . ?
C1' O2' C4 C3 6.2(11) . . . . ?
C1' O2' C4 C13' -118.7(11) . . . . ?
C1' O2' C4 C13 -100.7(12) . . . . ?
C3' C4 C5 C6 74.6(9) . . . . ?
O2 C4 C5 C6 -71.7(6) . . . . ?
C3 C4 C5 C6 49.7(8) . . . . ?
C13' C4 C5 C6 -147.0(7) . . . . ?
O2' C4 C5 C6 -40.0(8) . . . . ?
C13 C4 C5 C6 171.1(5) . . . . ?
C4 C5 C6 C7 172.4(4) . . . . ?
C5 C6 C7 C8 -108.5(5) . . . . ?
C5 C6 C7 C12 72.3(6) . . . . ?
C12 C7 C8 C9 -1.4(7) . . . . ?
C6 C7 C8 C9 179.4(4) . . . . ?
C7 C8 C9 C10 2.1(6) . . . . ?
C8 C9 C10 C11 -1.3(7) . . . . ?
C8 C9 C10 Br1 176.8(3) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
Br1 C10 C11 C12 -178.2(4) . . . . ?
C10 C11 C12 C7 0.7(8) . . . . ?
C8 C7 C12 C11 0.0(7) . . . . ?
C6 C7 C12 C11 179.2(4) . . . . ?
C14 O4 C13 O5 6.4(12) . . . . ?
C14 O4 C13 C4 -170.2(5) . . . . ?
C3' C4 C13 O5 23.3(10) . . . . ?
O2 C4 C13 O5 158.3(7) . . . . ?
C5 C4 C13 O5 -87.0(8) . . . . ?
C3 C4 C13 O5 39.7(9) . . . . ?
C13' C4 C13 O5 162.8(12) . . . . ?
O2' C4 C13 O5 134.5(9) . . . . ?
C3' C4 C13 O4 -160.0(9) . . . . ?
O2 C4 C13 O4 -25.0(8) . . . . ?
C5 C4 C13 O4 89.7(7) . . . . ?
C3 C4 C13 O4 -143.6(7) . . . . ?
C13' C4 C13 O4 -20.4(7) . . . . ?
O2' C4 C13 O4 -48.8(10) . . . . ?
C13 O4 C14 C16 61.8(9) . . . . ?
C13 O4 C14 C15 179.6(7) . . . . ?
C13 O4 C14 C17 -65.5(9) . . . . ?
C13 O4 C14 O4' 47.9(14) . . . . ?
C13' O4' C14 O4 -13.4(11) . . . . ?
C13' O4' C14 C16 179.0(12) . . . . ?
C13' O4' C14 C15 -67.7(13) . . . . ?
C13' O4' C14 C17 62.5(14) . . . . ?
C4 O2' C1' O1' 179.2(17) . . . . ?
C4 O2' C1' C2' -0.2(17) . . . . ?
O1' C1' C2' C3' 176.2(17) . . . . ?
O2' C1' C2' C3' -4(2) . . . . ?
O1' C1' C2' O3' -5(3) . . . . ?
O2' C1' C2' O3' 174.9(13) . . . . ?
O3' C2' C3' C4 -171.3(11) . . . . ?
C1' C2' C3' C4 8(2) . . . . ?
O3' C2' C3' C18' 2(3) . . . . ?
C1' C2' C3' C18' -178.8(15) . . . . ?
O2 C4 C3' C2' 9.3(19) . . . . ?
C5 C4 C3' C2' -125.5(12) . . . . ?
C3 C4 C3' C2' -12.0(13) . . . . ?
C13' C4 C3' C2' 98.3(15) . . . . ?
O2' C4 C3' C2' -7.8(15) . . . . ?
C13 C4 C3' C2' 127.1(13) . . . . ?
O2 C4 C3' C18' -164.9(8) . . . . ?
C5 C4 C3' C18' 60.3(12) . . . . ?
C3 C4 C3' C18' 174(3) . . . . ?
C13' C4 C3' C18' -75.8(14) . . . . ?
O2' C4 C3' C18' 178.0(10) . . . . ?
C13 C4 C3' C18' -47.0(11) . . . . ?
C14 O4' C13' O5' 2(2) . . . . ?
C14 O4' C13' C4 -169.5(8) . . . . ?
C3' C4 C13' O5' -80.8(17) . . . . ?
O2 C4 C13' O5' 46.2(14) . . . . ?
C5 C4 C13' O5' 145.5(12) . . . . ?
C3 C4 C13' O5' -52.8(17) . . . . ?
O2' C4 C13' O5' 30.3(15) . . . . ?
C13 C4 C13' O5' -129.2(17) . . . . ?
C3' C4 C13' O4' 91.5(13) . . . . ?
O2 C4 C13' O4' -141.4(12) . . . . ?
C5 C4 C13' O4' -42.1(12) . . . . ?
C3 C4 C13' O4' 119.6(11) . . . . ?
O2' C4 C13' O4' -157.4(11) . . . . ?
C13 C4 C13' O4' 43.1(9) . . . . ?

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
O3 H3 O1 0.84 2.44 2.849(7) 111.1 .
C9 H9 O1 0.95 2.58 3.477(6) 157.1 2_575
C16 H16A O5 0.98 2.57 3.084(9) 112.5 .
C17 H17A O5' 0.98 2.47 2.972(14) 111.4 .
C17 H17C O5 0.98 2.35 2.900(10) 115.0 .

_refine_diff_density_max         0.458
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-4

