# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

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

data_liu45s
_database_code_depnum_ccdc_archive 'CCDC 1520731'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H28 N4 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         520.53
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_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                   5.5338(6)
_cell_length_b                   16.6117(17)
_cell_length_c                   26.533(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2439.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9482
_cell_measurement_theta_min      2.6600
_cell_measurement_theta_max      67.1449
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096

_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4341
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_theta_min         3.14
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_full        68.25
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?

_refine_special_details          
;
;

_reflns_number_total             4341
_reflns_number_gt                4188
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1352
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         4341
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+2.8738P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_abs_structure_details 
;

Flack x determined using 1677 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(10)

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2035(6) 0.4681(2) 0.57680(13) 0.0154(8) Uani d . . . 1 . .
C C2 0.3432(7) 0.3879(2) 0.56889(14) 0.0171(7) Uani d . . . 1 . .
H H2A 0.4105 0.367 0.6013 0.021 Uiso calc U . R 1 . .
C C3 0.1836(7) 0.3267(2) 0.54376(14) 0.0212(8) Uani d . . . 1 . .
H H3 0.1048 0.2866 0.5633 0.025 Uiso calc U . R 1 . .
C C4 0.1530(7) 0.3286(2) 0.49413(14) 0.0213(8) Uani d . . . 1 . .
H H4A 0.0576 0.2882 0.4784 0.026 Uiso calc U . R 1 . .
C C5 0.2655(7) 0.3930(2) 0.46238(13) 0.0190(8) Uani d . . . 1 . .
H H5A 0.1324 0.4226 0.4448 0.023 Uiso calc U . R 1 . .
C C6 0.4026(7) 0.4540(2) 0.49560(13) 0.0165(8) Uani d . . . 1 . .
H H6A 0.5165 0.4868 0.4747 0.02 Uiso calc U . R 1 . .
C C7 0.2243(7) 0.5091(2) 0.52424(13) 0.0147(7) Uani d . . . 1 . .
H H7A 0.0638 0.5103 0.507 0.018 Uiso calc U . R 1 . .
C C8 0.3153(7) 0.5949(2) 0.53456(13) 0.0178(8) Uani d . . . 1 . .
H H8 0.4122 0.6152 0.5054 0.021 Uiso calc U . R 1 . .
C C9 0.1014(7) 0.6504(2) 0.54470(14) 0.0213(8) Uani d . . . 1 . .
H H9A 0.0146 0.6604 0.5127 0.026 Uiso calc U . R 1 . .
H H9B -0.0118 0.6233 0.568 0.026 Uiso calc U . R 1 . .
C C10 0.1765(8) 0.7309(2) 0.56739(16) 0.0250(9) Uani d . . . 1 . .
H H10A 0.032 0.7649 0.5727 0.03 Uiso calc U . R 1 . .
H H10B 0.2862 0.7594 0.5439 0.03 Uiso calc U . R 1 . .
C C11 0.3045(8) 0.7168(2) 0.61747(15) 0.0253(9) Uani d . . . 1 . .
H H11A 0.1934 0.6895 0.6412 0.03 Uiso calc U . R 1 . .
H H11B 0.3511 0.7692 0.6324 0.03 Uiso calc U . R 1 . .
C C12 0.5294(8) 0.6652(2) 0.60960(14) 0.0235(9) Uani d . . . 1 . .
H H12A 0.6013 0.6525 0.6428 0.028 Uiso calc U . R 1 . .
H H12B 0.6499 0.6965 0.5901 0.028 Uiso calc U . R 1 . .
C C13 0.4756(7) 0.5867(2) 0.58171(13) 0.0163(7) Uani d . . . 1 . .
H H13 0.6334 0.5629 0.5709 0.02 Uiso calc U . R 1 . .
C C14 0.3422(7) 0.5237(2) 0.61186(13) 0.0165(8) Uani d . . . 1 . .
C C15 0.4207(8) 0.4037(2) 0.38005(14) 0.0221(8) Uani d . . . 1 . .
H H15A 0.49 0.4572 0.3878 0.027 Uiso calc U . R 1 . .
H H15B 0.2547 0.4116 0.3671 0.027 Uiso calc U . R 1 . .
C C16 0.5731(7) 0.3623(2) 0.34054(14) 0.0202(8) Uani d . . . 1 . .
C C17 0.7854(7) 0.3215(2) 0.35253(15) 0.0237(9) Uani d . . . 1 . .
H H17 0.8345 0.3171 0.3867 0.028 Uiso calc U . R 1 . .
C C18 0.9259(8) 0.2873(3) 0.31479(17) 0.0300(9) Uani d . . . 1 . .
H H18 1.0683 0.2583 0.3232 0.036 Uiso calc U . R 1 . .
C C19 0.8572(8) 0.2956(3) 0.26457(16) 0.0306(10) Uani d . . . 1 . .
H H19 0.9549 0.2733 0.2387 0.037 Uiso calc U . R 1 . .
C C20 0.6473(8) 0.3363(3) 0.25231(15) 0.0272(9) Uani d . . . 1 . .
H H20 0.6004 0.3416 0.218 0.033 Uiso calc U . R 1 . .
C C21 0.5052(8) 0.3693(2) 0.29016(14) 0.0236(9) Uani d . . . 1 . .
H H21 0.3604 0.3969 0.2816 0.028 Uiso calc U . R 1 . .
C C22 0.2854(7) 0.4462(2) 0.73306(13) 0.0181(8) Uani d . . . 1 . .
C C23 0.1433(7) 0.3954(2) 0.76467(13) 0.0177(8) Uani d . . . 1 . .
C C24 0.1966(7) 0.3854(2) 0.81571(14) 0.0195(8) Uani d . . . 1 . .
H H24 0.0987 0.352 0.8364 0.023 Uiso calc U . R 1 . .
C C25 0.3931(8) 0.4247(2) 0.83547(13) 0.0202(8) Uani d . . . 1 . .
C C26 0.5401(7) 0.4736(2) 0.80578(14) 0.0202(8) Uani d . . . 1 . .
H H26 0.6766 0.4996 0.8201 0.024 Uiso calc U . R 1 . .
C C27 0.4869(7) 0.4840(2) 0.75590(14) 0.0195(8) Uani d . . . 1 . .
H H27 0.5879 0.5175 0.736 0.023 Uiso calc U . R 1 . .
N N1 0.3633(6) 0.52020(19) 0.65989(11) 0.0194(7) Uani d . . . 1 . .
N N2 0.2355(6) 0.45917(19) 0.68395(12) 0.0192(7) Uani d . . . 1 . .
H H1N 0.104(10) 0.434(3) 0.6690(17) 0.029 Uiso d U . . 1 . .
N N3 -0.0665(6) 0.35312(19) 0.74593(11) 0.0205(7) Uani d . . . 1 . .
N N4 0.4462(7) 0.4160(2) 0.88891(12) 0.0242(8) Uani d . . . 1 . .
O O1 0.5325(5) 0.41099(15) 0.53460(9) 0.0178(6) Uani d . . . 1 . .
O O2 -0.0342(5) 0.45713(16) 0.59632(9) 0.0185(6) Uani d . . . 1 . .
H H2 -0.1248 0.4394 0.5735 0.028 Uiso calc U . R 1 . .
O O3 0.4133(5) 0.35622(15) 0.42473(9) 0.0207(6) Uani d . . . 1 . .
O O4 -0.1192(6) 0.35827(19) 0.70068(10) 0.0297(7) Uani d . . . 1 . .
O O5 -0.1883(6) 0.31391(17) 0.77583(11) 0.0275(7) Uani d . . . 1 . .
O O6 0.3043(6) 0.3781(2) 0.91545(10) 0.0343(8) Uani d . . . 1 . .
O O7 0.6299(6) 0.4480(2) 0.90560(11) 0.0355(8) Uani d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O2 . 1.426(4) ?
C1 C14 . 1.519(5) ?
C1 C2 . 1.555(5) ?
C1 C7 . 1.556(5) ?
C2 O1 . 1.440(4) ?
C2 C3 . 1.503(5) ?
C3 C4 . 1.328(5) ?
C4 C5 . 1.497(5) ?
C5 O3 . 1.429(4) ?
C5 C6 . 1.542(5) ?
C6 O1 . 1.448(4) ?
C6 C7 . 1.545(5) ?
C7 C8 . 1.537(5) ?
C8 C9 . 1.524(5) ?
C8 C13 . 1.540(5) ?
C9 C10 . 1.523(6) ?
C10 C11 . 1.524(6) ?
C11 C12 . 1.526(6) ?
C12 C13 . 1.530(5) ?
C13 C14 . 1.510(5) ?
C14 N1 . 1.281(5) ?
C15 O3 . 1.425(4) ?
C15 C16 . 1.511(5) ?
C16 C17 . 1.393(6) ?
C16 C21 . 1.393(5) ?
C17 C18 . 1.389(6) ?
C18 C19 . 1.393(6) ?
C19 C20 . 1.382(6) ?
C20 C21 . 1.389(6) ?
C22 N2 . 1.349(5) ?
C22 C27 . 1.416(5) ?
C22 C23 . 1.426(5) ?
C23 C24 . 1.396(5) ?
C23 N3 . 1.445(5) ?
C24 C25 . 1.372(6) ?
C25 C26 . 1.394(6) ?
C25 N4 . 1.455(5) ?
C26 C27 . 1.367(5) ?
N1 N2 . 1.391(4) ?
N3 O5 . 1.228(4) ?
N3 O4 . 1.239(4) ?
N4 O6 . 1.229(5) ?
N4 O7 . 1.230(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 C14 . . 108.7(3) ?
O2 C1 C2 . . 113.5(3) ?
C14 C1 C2 . . 110.7(3) ?
O2 C1 C7 . . 116.7(3) ?
C14 C1 C7 . . 104.2(3) ?
C2 C1 C7 . . 102.5(3) ?
O1 C2 C3 . . 109.1(3) ?
O1 C2 C1 . . 102.6(3) ?
C3 C2 C1 . . 110.4(3) ?
C4 C3 C2 . . 119.9(4) ?
C3 C4 C5 . . 121.5(4) ?
O3 C5 C4 . . 109.0(3) ?
O3 C5 C6 . . 113.5(3) ?
C4 C5 C6 . . 110.6(3) ?
O1 C6 C5 . . 109.2(3) ?
O1 C6 C7 . . 104.9(3) ?
C5 C6 C7 . . 110.8(3) ?
C8 C7 C6 . . 115.3(3) ?
C8 C7 C1 . . 105.7(3) ?
C6 C7 C1 . . 103.2(3) ?
C9 C8 C7 . . 109.8(3) ?
C9 C8 C13 . . 111.0(3) ?
C7 C8 C13 . . 104.5(3) ?
C10 C9 C8 . . 112.9(3) ?
C9 C10 C11 . . 109.7(3) ?
C10 C11 C12 . . 110.2(3) ?
C11 C12 C13 . . 112.7(3) ?
C14 C13 C12 . . 115.5(3) ?
C14 C13 C8 . . 102.2(3) ?
C12 C13 C8 . . 115.4(3) ?
N1 C14 C13 . . 120.9(3) ?
N1 C14 C1 . . 128.9(3) ?
C13 C14 C1 . . 110.1(3) ?
O3 C15 C16 . . 110.0(3) ?
C17 C16 C21 . . 119.2(4) ?
C17 C16 C15 . . 122.2(4) ?
C21 C16 C15 . . 118.5(4) ?
C18 C17 C16 . . 120.4(4) ?
C17 C18 C19 . . 119.8(4) ?
C20 C19 C18 . . 120.2(4) ?
C19 C20 C21 . . 119.9(4) ?
C20 C21 C16 . . 120.5(4) ?
N2 C22 C27 . . 120.2(3) ?
N2 C22 C23 . . 123.3(4) ?
C27 C22 C23 . . 116.4(3) ?
C24 C23 C22 . . 121.6(3) ?
C24 C23 N3 . . 116.5(3) ?
C22 C23 N3 . . 121.9(3) ?
C25 C24 C23 . . 118.8(3) ?
C24 C25 C26 . . 121.6(3) ?
C24 C25 N4 . . 119.0(3) ?
C26 C25 N4 . . 119.4(4) ?
C27 C26 C25 . . 119.7(4) ?
C26 C27 C22 . . 121.9(4) ?
C14 N1 N2 . . 116.3(3) ?
C22 N2 N1 . . 117.1(3) ?
O5 N3 O4 . . 122.3(3) ?
O5 N3 C23 . . 118.5(3) ?
O4 N3 C23 . . 119.3(3) ?
O6 N4 O7 . . 123.0(3) ?
O6 N4 C25 . . 118.7(3) ?
O7 N4 C25 . . 118.3(3) ?
C2 O1 C6 . . 102.8(3) ?
C15 O3 C5 . . 111.2(3) ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1436794'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         348.38
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_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                   5.8597(6)
_cell_length_b                   8.4350(8)
_cell_length_c                   35.607(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1759.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4238
_cell_measurement_theta_min      2.9628
_cell_measurement_theta_max      22.7852
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736

_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_monochromator  graphite

_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            12377
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42

_refine_special_details          
;
;

_reflns_number_total             3111
_reflns_number_gt                2754
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0978
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_number_reflns         3111
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0376P)²+0.7934P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?


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'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3755(6) 0.4884(4) 0.15220(9) 0.0230(7) Uani d . . . 1 . .
C C2 0.5503(6) 0.5545(4) 0.17316(10) 0.0318(9) Uani d . . . 1 . .
H H2 0.6702 0.6097 0.1608 0.038 Uiso calc U . R 1 . .
C C3 0.5518(7) 0.5409(5) 0.21197(10) 0.0373(10) Uani d . . . 1 . .
H H3 0.6723 0.5867 0.2261 0.045 Uiso calc U . R 1 . .
C C4 0.3787(7) 0.4608(5) 0.22997(9) 0.0381(10) Uani d . . . 1 . .
H H4 0.3792 0.452 0.2566 0.046 Uiso calc U . R 1 . .
C C5 0.2046(7) 0.3936(5) 0.20937(9) 0.0355(10) Uani d . . . 1 . .
H H5 0.0857 0.3377 0.2218 0.043 Uiso calc U . R 1 . .
C C6 0.2028(6) 0.4077(4) 0.17036(9) 0.0265(8) Uani d . . . 1 . .
H H6 0.0824 0.3616 0.1562 0.032 Uiso calc U . R 1 . .
C C7 0.3828(5) 0.5021(4) 0.11009(9) 0.0252(8) Uani d . . . 1 . .
H H7A 0.4297 0.6106 0.1028 0.03 Uiso calc U . R 1 . .
H H7B 0.4957 0.4265 0.0998 0.03 Uiso calc U . R 1 . .
C C8 0.1604(5) 0.4279(4) 0.05638(8) 0.0167(7) Uani d . . . 1 . .
H H8 0.2866 0.3512 0.0511 0.02 Uiso calc U . R 1 . .
C C9 -0.0637(5) 0.3496(4) 0.04869(8) 0.0173(7) Uani d . . . 1 . .
H H9 -0.0999 0.2536 0.0613 0.021 Uiso calc U . R 1 . .
C C10 -0.2135(5) 0.4103(4) 0.02476(9) 0.0179(7) Uani d . . . 1 . .
H H10 -0.3526 0.357 0.0195 0.021 Uiso calc U . R 1 . .
C C11 -0.1572(5) 0.5664(4) 0.00611(8) 0.0174(7) Uani d . . . 1 . .
H H11 -0.2965 0.6239 -0.0027 0.021 Uiso calc U . R 1 . .
C C12 0.1901(5) 0.5748(4) 0.03140(8) 0.0167(7) Uani d . . . 1 . .
H H12 0.318 0.6432 0.0405 0.02 Uiso calc U . R 1 . .
C C13 0.2189(5) 0.5338(3) -0.00976(8) 0.0157(7) Uani d . . . 1 . .
H H13 0.3587 0.5107 -0.0221 0.019 Uiso calc U . R 1 . .
C C14 0.0132(5) 0.5362(3) -0.02552(8) 0.0151(7) Uani d . . . 1 . .
C C15 -0.0678(5) 0.4923(4) -0.06329(9) 0.0186(7) Uani d . . . 1 . .
C C16 0.0848(5) 0.5029(4) -0.09627(8) 0.0202(7) Uani d . . . 1 . .
C C17 0.2708(5) 0.6045(4) -0.09794(8) 0.0193(7) Uani d . . . 1 . .
H H17 0.3071 0.6682 -0.0768 0.023 Uiso calc U . R 1 . .
C C18 0.4044(6) 0.6147(4) -0.12993(8) 0.0215(8) Uani d . . . 1 . .
H H18 0.5294 0.6863 -0.1309 0.026 Uiso calc U . R 1 . .
C C19 0.3540(6) 0.5194(4) -0.16059(8) 0.0268(8) Uani d . . . 1 . .
C C20 0.1695(7) 0.4162(4) -0.15923(9) 0.0307(9) Uani d . . . 1 . .
H H20 0.1363 0.3502 -0.1802 0.037 Uiso calc U . R 1 . .
C C21 0.0351(6) 0.4093(4) -0.12777(9) 0.0270(8) Uani d . . . 1 . .
H H21 -0.0931 0.3404 -0.1273 0.032 Uiso calc U . R 1 . .
C C22 0.6500(7) 0.6369(5) -0.19714(10) 0.0386(10) Uani d . . . 1 . .
H H22A 0.5854 0.743 -0.1937 0.058 Uiso calc U . R 1 . .
H H22B 0.7179 0.6291 -0.2222 0.058 Uiso calc U . R 1 . .
H H22C 0.7678 0.618 -0.1781 0.058 Uiso calc U . R 1 . .
O O1 0.1632(4) 0.4685(3) 0.09529(5) 0.0216(5) Uani d . . . 1 . .
O O2 -0.0224(4) 0.6594(2) 0.03156(6) 0.0185(5) Uani d . . . 1 . .
O O3 -0.2652(4) 0.4440(3) -0.06592(6) 0.0265(6) Uani d . . . 1 . .
O O4 0.4742(4) 0.5213(3) -0.19339(6) 0.0355(6) Uani d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.381(5) ?
C1 C2 . 1.384(5) ?
C1 C7 . 1.505(4) ?
C2 C3 . 1.387(5) ?
C3 C4 . 1.377(5) ?
C4 C5 . 1.379(5) ?
C5 C6 . 1.394(4) ?
C7 O1 . 1.419(4) ?
C8 O1 . 1.428(3) ?
C8 C9 . 1.495(4) ?
C8 C12 . 1.535(4) ?
C9 C10 . 1.326(4) ?
C10 C11 . 1.511(4) ?
C11 O2 . 1.436(4) ?
C11 C14 . 1.527(4) ?
C12 O2 . 1.435(4) ?
C12 C13 . 1.515(4) ?
C13 C14 . 1.330(4) ?
C14 C15 . 1.473(4) ?
C15 O3 . 1.230(4) ?
C15 C16 . 1.479(4) ?
C16 C17 . 1.388(4) ?
C16 C21 . 1.402(4) ?
C17 C18 . 1.385(4) ?
C18 C19 . 1.388(5) ?
C19 O4 . 1.364(4) ?
C19 C20 . 1.389(5) ?
C20 C21 . 1.370(5) ?
C22 O4 . 1.425(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.2(3) ?
C6 C1 C7 . . 121.7(3) ?
C2 C1 C7 . . 119.0(3) ?
C1 C2 C3 . . 120.6(3) ?
C4 C3 C2 . . 120.0(3) ?
C3 C4 C5 . . 119.9(3) ?
C4 C5 C6 . . 120.0(4) ?
C1 C6 C5 . . 120.2(3) ?
O1 C7 C1 . . 109.2(3) ?
O1 C8 C9 . . 107.1(2) ?
O1 C8 C12 . . 111.6(2) ?
C9 C8 C12 . . 110.5(3) ?
C10 C9 C8 . . 121.9(3) ?
C9 C10 C11 . . 118.3(3) ?
O2 C11 C10 . . 108.6(2) ?
O2 C11 C14 . . 101.4(2) ?
C10 C11 C14 . . 108.8(2) ?
O2 C12 C13 . . 102.3(2) ?
O2 C12 C8 . . 107.5(2) ?
C13 C12 C8 . . 112.9(2) ?
C14 C13 C12 . . 107.7(3) ?
C13 C14 C15 . . 132.3(3) ?
C13 C14 C11 . . 106.5(3) ?
C15 C14 C11 . . 120.3(3) ?
O3 C15 C14 . . 117.1(3) ?
O3 C15 C16 . . 121.9(3) ?
C14 C15 C16 . . 121.0(3) ?
C17 C16 C21 . . 118.5(3) ?
C17 C16 C15 . . 123.1(3) ?
C21 C16 C15 . . 118.4(3) ?
C18 C17 C16 . . 121.2(3) ?
C17 C18 C19 . . 119.4(3) ?
O4 C19 C18 . . 123.8(3) ?
O4 C19 C20 . . 116.1(3) ?
C18 C19 C20 . . 120.1(3) ?
C21 C20 C19 . . 120.2(3) ?
C20 C21 C16 . . 120.7(3) ?
C7 O1 C8 . . 114.7(2) ?
C12 O2 C11 . . 101.7(2) ?
C19 O4 C22 . . 117.5(3) ?

