# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 2015920'
loop_
_audit_author_name
_audit_author_address
zhaocan
;shanghaijiaotong university
China
;
_audit_update_record             
;
2020-07-12 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H21 N O7'
_chemical_formula_sum            'C17 H21 N O7'
_chemical_formula_weight         351.35

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'

_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                   6.921(6)
_cell_length_b                   10.91(3)
_cell_length_c                   24.068(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1817(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      3.67
_cell_measurement_theta_max      64.89

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.6337
_exptl_transmission_factor_max   0.7526
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.846
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21728
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.673
_diffrn_reflns_theta_max         65.128
_diffrn_reflns_theta_full        65.128
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3094
_reflns_number_gt                2662
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0640P)²+0.1678P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 973 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(8)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         3094
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.5229(4) 0.4377(2) 0.58495(9) 0.0906(7) Uani 1 1 d . . . . .
C1 C 0.5345(5) 0.7064(2) 0.38409(12) 0.0713(7) Uani 1 1 d . . . . .
H1 H 0.663278 0.696446 0.367792 0.086 Uiso 1 1 calc R U . . .
N1 N 0.4726(4) 0.6485(3) 0.28314(11) 0.0815(7) Uani 1 1 d . . . . .
O2 O 0.7940(4) 0.3977(2) 0.51447(10) 0.0957(7) Uani 1 1 d . . . . .
C2 C 0.3802(4) 0.6684(2) 0.34011(10) 0.0636(6) Uani 1 1 d . . . . .
O4 O 0.3822(5) 0.5860(2) 0.24996(10) 0.1044(8) Uani 1 1 d . . . . .
C4 C 0.3878(6) 0.8840(3) 0.35073(14) 0.0869(9) Uani 1 1 d . . . . .
H4A H 0.467737 0.906204 0.319189 0.104 Uiso 1 1 calc R U . . .
H4B H 0.318559 0.956144 0.363358 0.104 Uiso 1 1 calc R U . . .
O3 O 0.5013(4) 0.83373(18) 0.39409(10) 0.0959(8) Uani 1 1 d . . . . .
C3 C 0.2492(5) 0.7822(3) 0.33564(13) 0.0735(7) Uani 1 1 d . . . . .
H3 H 0.155456 0.776590 0.366053 0.088 Uiso 1 1 calc R U . . .
O5 O 0.6236(4) 0.7009(3) 0.27261(11) 0.1159(9) Uani 1 1 d . . . . .
C5 C 0.1350(6) 0.7972(3) 0.28324(17) 0.0985(11) Uani 1 1 d . . . . .
H5 H 0.045022 0.736434 0.275237 0.118 Uiso 1 1 calc R U . . .
O7 O 0.3909(3) 0.45696(17) 0.35170(9) 0.0816(6) Uani 1 1 d . . . . .
C7 C 0.2717(5) 0.5504(3) 0.35354(11) 0.0693(7) Uani 1 1 d . . . . .
O6 O 0.1045(4) 0.5464(2) 0.36584(10) 0.0894(7) Uani 1 1 d . . . . .
C6 C 0.1489(9) 0.8848(5) 0.2486(2) 0.143(2) Uani 1 1 d . . . . .
H6A H 0.236828 0.947865 0.254748 0.172 Uiso 1 1 calc R U . . .
H6B H 0.071076 0.885867 0.217090 0.172 Uiso 1 1 calc R U . . .
C9 C 0.4737(8) 0.2534(3) 0.37352(19) 0.1192(15) Uani 1 1 d . . . . .
H9A H 0.536607 0.243812 0.338233 0.179 Uiso 1 1 calc R U . . .
H9B H 0.425732 0.175405 0.385828 0.179 Uiso 1 1 calc R U . . .
H9C H 0.564449 0.284536 0.400186 0.179 Uiso 1 1 calc R U . . .
C8 C 0.3160(7) 0.3377(3) 0.3680(2) 0.1181(15) Uani 1 1 d . . . . .
H8A H 0.247713 0.344517 0.403065 0.142 Uiso 1 1 calc R U . . .
H8B H 0.226011 0.308118 0.340160 0.142 Uiso 1 1 calc R U . . .
C10 C 0.5278(4) 0.6385(2) 0.43856(11) 0.0665(7) Uani 1 1 d . . . . .
C11 C 0.3842(5) 0.6607(3) 0.47704(12) 0.0758(8) Uani 1 1 d . . . . .
H11 H 0.290651 0.719848 0.469845 0.091 Uiso 1 1 calc R U . . .
C12 C 0.3789(5) 0.5952(3) 0.52639(12) 0.0779(8) Uani 1 1 d . . . . .
H12 H 0.281418 0.610642 0.552059 0.093 Uiso 1 1 calc R U . . .
C13 C 0.5163(5) 0.5077(3) 0.53771(11) 0.0711(7) Uani 1 1 d . . . . .
C14 C 0.6638(4) 0.4855(3) 0.49951(12) 0.0705(7) Uani 1 1 d . . . . .
C15 C 0.6689(4) 0.5515(3) 0.45051(11) 0.0684(7) Uani 1 1 d . . . . .
H15 H 0.767952 0.537633 0.425181 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3757(7) 0.4569(4) 0.62512(15) 0.1074(12) Uani 1 1 d . . . . .
H16A H 0.375440 0.541371 0.636313 0.161 Uiso 1 1 calc R U . . .
H16B H 0.399549 0.405846 0.656892 0.161 Uiso 1 1 calc R U . . .
H16C H 0.252482 0.436364 0.609323 0.161 Uiso 1 1 calc R U . . .
C17 C 0.9521(6) 0.3756(4) 0.47905(17) 0.1048(12) Uani 1 1 d . . . . .
H17A H 0.906025 0.346260 0.443861 0.157 Uiso 1 1 calc R U . . .
H17B H 1.035167 0.315232 0.495492 0.157 Uiso 1 1 calc R U . . .
H17C H 1.022778 0.450430 0.473650 0.157 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 C13 1.370(4) . ?
O1 C16 1.420(4) . ?
C1 O3 1.428(5) . ?
C1 C10 1.506(4) . ?
C1 C2 1.560(4) . ?
C1 H1 0.9800 . ?
N1 O5 1.218(4) . ?
N1 O4 1.222(4) . ?
N1 C2 1.529(4) . ?
O2 C14 1.363(4) . ?
O2 C17 1.407(5) . ?
C2 C7 1.525(5) . ?
C2 C3 1.541(5) . ?
C4 O3 1.416(4) . ?
C4 C3 1.512(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 C5 1.497(5) . ?
C3 H3 0.9800 . ?
C5 C6 1.272(6) . ?
C5 H5 0.9300 . ?
O7 C7 1.312(4) . ?
O7 C8 1.454(5) . ?
C7 O6 1.196(4) . ?
C6 H6A 0.9300 . ?
C6 H6B 0.9300 . ?
C9 C8 1.433(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.380(4) . ?
C10 C15 1.391(4) . ?
C11 C12 1.386(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(4) . ?
C14 C15 1.382(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
C13 O1 C16 117.3(3) . . ?
O3 C1 C10 109.1(3) . . ?
O3 C1 C2 105.2(2) . . ?
C10 C1 C2 116.1(2) . . ?
O3 C1 H1 108.8 . . ?
C10 C1 H1 108.8 . . ?
C2 C1 H1 108.8 . . ?
O5 N1 O4 124.4(3) . . ?
O5 N1 C2 118.6(3) . . ?
O4 N1 C2 116.8(3) . . ?
C14 O2 C17 118.3(2) . . ?
C7 C2 N1 106.0(2) . . ?
C7 C2 C3 113.9(3) . . ?
N1 C2 C3 107.4(2) . . ?
C7 C2 C1 114.7(2) . . ?
N1 C2 C1 111.1(2) . . ?
C3 C2 C1 103.7(2) . . ?
O3 C4 C3 104.2(3) . . ?
O3 C4 H4A 110.9 . . ?
C3 C4 H4A 110.9 . . ?
O3 C4 H4B 110.9 . . ?
C3 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
C4 O3 C1 110.0(2) . . ?
C5 C3 C4 117.2(3) . . ?
C5 C3 C2 117.2(3) . . ?
C4 C3 C2 101.6(3) . . ?
C5 C3 H3 106.7 . . ?
C4 C3 H3 106.7 . . ?
C2 C3 H3 106.7 . . ?
C6 C5 C3 126.5(4) . . ?
C6 C5 H5 116.8 . . ?
C3 C5 H5 116.8 . . ?
C7 O7 C8 117.5(3) . . ?
O6 C7 O7 126.1(3) . . ?
O6 C7 C2 124.1(3) . . ?
O7 C7 C2 109.8(3) . . ?
C5 C6 H6A 120.0 . . ?
C5 C6 H6B 120.0 . . ?
H6A C6 H6B 120.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C9 C8 O7 109.1(4) . . ?
C9 C8 H8A 109.9 . . ?
O7 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
O7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C11 C10 C15 119.1(3) . . ?
C11 C10 C1 121.3(3) . . ?
C15 C10 C1 119.6(3) . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C12 125.1(3) . . ?
O1 C13 C14 115.2(3) . . ?
C12 C13 C14 119.8(3) . . ?
O2 C14 C15 125.1(3) . . ?
O2 C14 C13 115.6(2) . . ?
C15 C14 C13 119.4(3) . . ?
C14 C15 C10 120.9(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O5 N1 C2 C7 -150.0(3) . . . . ?
O4 N1 C2 C7 34.3(3) . . . . ?
O5 N1 C2 C3 87.9(3) . . . . ?
O4 N1 C2 C3 -87.8(3) . . . . ?
O5 N1 C2 C1 -24.9(4) . . . . ?
O4 N1 C2 C1 159.5(3) . . . . ?
O3 C1 C2 C7 -132.9(3) . . . . ?
C10 C1 C2 C7 -12.2(4) . . . . ?
O3 C1 C2 N1 107.0(3) . . . . ?
C10 C1 C2 N1 -132.4(3) . . . . ?
O3 C1 C2 C3 -8.1(3) . . . . ?
C10 C1 C2 C3 112.6(3) . . . . ?
C3 C4 O3 C1 36.1(4) . . . . ?
C10 C1 O3 C4 -142.3(3) . . . . ?
C2 C1 O3 C4 -17.2(3) . . . . ?
O3 C4 C3 C5 -168.0(3) . . . . ?
O3 C4 C3 C2 -38.9(3) . . . . ?
C7 C2 C3 C5 -77.6(3) . . . . ?
N1 C2 C3 C5 39.4(4) . . . . ?
C1 C2 C3 C5 157.1(3) . . . . ?
C7 C2 C3 C4 153.3(2) . . . . ?
N1 C2 C3 C4 -89.7(3) . . . . ?
C1 C2 C3 C4 28.0(3) . . . . ?
C4 C3 C5 C6 3.4(7) . . . . ?
C2 C3 C5 C6 -117.9(5) . . . . ?
C8 O7 C7 O6 -2.4(5) . . . . ?
C8 O7 C7 C2 175.0(3) . . . . ?
N1 C2 C7 O6 -126.0(3) . . . . ?
C3 C2 C7 O6 -8.1(4) . . . . ?
C1 C2 C7 O6 111.1(3) . . . . ?
N1 C2 C7 O7 56.6(3) . . . . ?
C3 C2 C7 O7 174.4(2) . . . . ?
C1 C2 C7 O7 -66.4(3) . . . . ?
C7 O7 C8 C9 -169.0(3) . . . . ?
O3 C1 C10 C11 45.2(4) . . . . ?
C2 C1 C10 C11 -73.4(4) . . . . ?
O3 C1 C10 C15 -134.9(3) . . . . ?
C2 C1 C10 C15 106.6(3) . . . . ?
C15 C10 C11 C12 -1.3(4) . . . . ?
C1 C10 C11 C12 178.7(3) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C16 O1 C13 C12 0.3(5) . . . . ?
C16 O1 C13 C14 -179.9(3) . . . . ?
C11 C12 C13 O1 -179.5(3) . . . . ?
C11 C12 C13 C14 0.7(5) . . . . ?
C17 O2 C14 C15 3.4(5) . . . . ?
C17 O2 C14 C13 -176.6(3) . . . . ?
O1 C13 C14 O2 -0.2(4) . . . . ?
C12 C13 C14 O2 179.6(3) . . . . ?
O1 C13 C14 C15 179.9(3) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
O2 C14 C15 C10 179.2(3) . . . . ?
C13 C14 C15 C10 -0.8(4) . . . . ?
C11 C10 C15 C14 1.6(4) . . . . ?
C1 C10 C15 C14 -178.3(3) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.024

####################################################################### 
# 
# 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_ta_a
_database_code_depnum_ccdc_archive 'CCDC 2015921'
loop_
_audit_author_name
_audit_author_address
zhaocan
;shanghaijiaotong university
China
;
_audit_update_record             
;
2020-07-12 deposited with the CCDC.	2020-09-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 O5'
_chemical_formula_sum            'C13 H12 O5'
_chemical_formula_weight         248.23

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'

_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                   6.6885(3)
_cell_length_b                   7.1093(3)
_cell_length_c                   24.1880(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1150.15(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8692
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      68.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.6575
_exptl_transmission_factor_max   0.7531
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.938
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.872
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12764
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.655
_diffrn_reflns_theta_max         68.391
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2095
_reflns_number_gt                1610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.995

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0522P)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_abs_structure_details 
;
 Flack x determined using 572 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(9)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2095
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0898
_refine_ls_wR_factor_gt          0.0805
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.9581(3) 0.6850(2) 0.40818(8) 0.0528(5) Uani 1 1 d . . . . .
C1 C 1.0710(4) 0.9096(4) 0.29127(12) 0.0546(6) Uani 1 1 d . . . . .
O2 O 0.9306(3) 0.8575(3) 0.25413(8) 0.0677(6) Uani 1 1 d . . . . .
C2 C 0.9779(3) 0.9439(3) 0.34691(11) 0.0453(6) Uani 1 1 d . . . . .
H2 H 0.964744 1.078529 0.354753 0.054 Uiso 1 1 calc R U . . .
O3 O 1.2437(3) 0.9197(3) 0.27898(10) 0.0758(6) Uani 1 1 d . . . . .
C3 C 1.0828(4) 0.8402(4) 0.39387(12) 0.0556(6) Uani 1 1 d . . . . .
H3A H 1.213216 0.796283 0.381978 0.067 Uiso 1 1 calc R U . . .
H3B H 1.100386 0.922880 0.425399 0.067 Uiso 1 1 calc R U . . .
C6 C 0.8192(4) 0.6526(3) 0.36402(10) 0.0432(5) Uani 1 1 d . . . . .
H6 H 0.885028 0.578295 0.335146 0.052 Uiso 1 1 calc R U . . .
O5 O 0.2757(3) 0.5234(3) 0.49826(8) 0.0594(5) Uani 1 1 d . . . . .
C5 C 0.7740(4) 0.8488(3) 0.34146(11) 0.0451(5) Uani 1 1 d . . . . .
H5 H 0.670386 0.913398 0.362915 0.054 Uiso 1 1 calc R U . . .
O4 O 0.1420(3) 0.2836(3) 0.44552(9) 0.0649(6) Uani 1 1 d . . . . .
C4 C 0.7337(4) 0.8564(4) 0.27965(12) 0.0603(7) Uani 1 1 d . . . . .
H4A H 0.657523 0.747485 0.267837 0.072 Uiso 1 1 calc R U . . .
H4B H 0.659920 0.969290 0.270072 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6419(4) 0.5459(3) 0.38517(10) 0.0422(5) Uani 1 1 d . . . . .
C9 C 0.3854(3) 0.5015(3) 0.45107(10) 0.0425(5) Uani 1 1 d . . . . .
C8 C 0.5532(3) 0.5970(3) 0.43562(10) 0.0423(5) Uani 1 1 d . . . . .
H8 H 0.606582 0.691885 0.457565 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3046(4) 0.3587(3) 0.41924(11) 0.0464(6) Uani 1 1 d . . . . .
C11 C 0.3884(4) 0.3055(4) 0.37054(12) 0.0561(7) Uani 1 1 d . . . . .
H11 H 0.333716 0.209503 0.349235 0.067 Uiso 1 1 calc R U . . .
C12 C 0.5603(4) 0.4015(3) 0.35390(11) 0.0519(6) Uani 1 1 d . . . . .
H12 H 0.621887 0.367661 0.320892 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1168(4) 0.3884(4) 0.49522(13) 0.0643(8) Uani 1 1 d . . . . .
H13A H 0.121465 0.305028 0.526946 0.077 Uiso 1 1 calc R U . . .
H13B H -0.011573 0.451889 0.495037 0.077 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 C3 1.426(3) . ?
O1 C6 1.434(3) . ?
C1 O3 1.195(3) . ?
C1 O2 1.351(4) . ?
C1 C2 1.503(4) . ?
O2 C4 1.455(3) . ?
C2 C3 1.525(4) . ?
C2 C5 1.527(3) . ?
C2 H2 0.9800 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 C7 1.497(3) . ?
C6 C5 1.528(3) . ?
C6 H6 0.9800 . ?
O5 C9 1.366(3) . ?
O5 C13 1.434(3) . ?
C5 C4 1.520(3) . ?
C5 H5 0.9800 . ?
O4 C10 1.368(3) . ?
O4 C13 1.424(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C7 C12 1.387(3) . ?
C7 C8 1.405(3) . ?
C9 C8 1.364(3) . ?
C9 C10 1.384(3) . ?
C8 H8 0.9300 . ?
C10 C11 1.358(4) . ?
C11 C12 1.397(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C6 108.83(18) . . ?
O3 C1 O2 121.5(3) . . ?
O3 C1 C2 127.9(3) . . ?
O2 C1 C2 110.6(2) . . ?
C1 O2 C4 110.4(2) . . ?
C1 C2 C3 113.4(2) . . ?
C1 C2 C5 102.8(2) . . ?
C3 C2 C5 105.16(19) . . ?
C1 C2 H2 111.7 . . ?
C3 C2 H2 111.7 . . ?
C5 C2 H2 111.7 . . ?
O1 C3 C2 106.6(2) . . ?
O1 C3 H3A 110.4 . . ?
C2 C3 H3A 110.4 . . ?
O1 C3 H3B 110.4 . . ?
C2 C3 H3B 110.4 . . ?
H3A C3 H3B 108.6 . . ?
O1 C6 C7 109.9(2) . . ?
O1 C6 C5 104.30(18) . . ?
C7 C6 C5 115.3(2) . . ?
O1 C6 H6 109.0 . . ?
C7 C6 H6 109.0 . . ?
C5 C6 H6 109.0 . . ?
C9 O5 C13 106.19(19) . . ?
C4 C5 C2 103.2(2) . . ?
C4 C5 C6 114.7(2) . . ?
C2 C5 C6 101.33(19) . . ?
C4 C5 H5 112.2 . . ?
C2 C5 H5 112.2 . . ?
C6 C5 H5 112.2 . . ?
C10 O4 C13 106.40(19) . . ?
O2 C4 C5 104.9(2) . . ?
O2 C4 H4A 110.8 . . ?
C5 C4 H4A 110.8 . . ?
O2 C4 H4B 110.8 . . ?
C5 C4 H4B 110.8 . . ?
H4A C4 H4B 108.8 . . ?
C12 C7 C8 119.9(2) . . ?
C12 C7 C6 120.0(2) . . ?
C8 C7 C6 120.0(2) . . ?
C8 C9 O5 127.9(2) . . ?
C8 C9 C10 122.3(2) . . ?
O5 C9 C10 109.8(2) . . ?
C9 C8 C7 117.2(2) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C11 C10 O4 128.5(2) . . ?
C11 C10 C9 121.7(2) . . ?
O4 C10 C9 109.8(2) . . ?
C10 C11 C12 117.0(2) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
C7 C12 C11 121.9(2) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
O4 C13 O5 107.8(2) . . ?
O4 C13 H13A 110.1 . . ?
O5 C13 H13A 110.1 . . ?
O4 C13 H13B 110.1 . . ?
O5 C13 H13B 110.1 . . ?
H13A C13 H13B 108.5 . . ?

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
O3 C1 O2 C4 179.9(3) . . . . ?
C2 C1 O2 C4 1.5(3) . . . . ?
O3 C1 C2 C3 -49.1(4) . . . . ?
O2 C1 C2 C3 129.2(2) . . . . ?
O3 C1 C2 C5 -162.0(3) . . . . ?
O2 C1 C2 C5 16.2(3) . . . . ?
C6 O1 C3 C2 17.1(3) . . . . ?
C1 C2 C3 O1 -104.6(2) . . . . ?
C5 C2 C3 O1 7.0(3) . . . . ?
C3 O1 C6 C7 -158.5(2) . . . . ?
C3 O1 C6 C5 -34.4(2) . . . . ?
C1 C2 C5 C4 -26.3(2) . . . . ?
C3 C2 C5 C4 -145.2(2) . . . . ?
C1 C2 C5 C6 92.8(2) . . . . ?
C3 C2 C5 C6 -26.2(3) . . . . ?
O1 C6 C5 C4 147.02(19) . . . . ?
C7 C6 C5 C4 -92.4(3) . . . . ?
O1 C6 C5 C2 36.7(2) . . . . ?
C7 C6 C5 C2 157.2(2) . . . . ?
C1 O2 C4 C5 -18.9(3) . . . . ?
C2 C5 C4 O2 27.8(3) . . . . ?
C6 C5 C4 O2 -81.5(3) . . . . ?
O1 C6 C7 C12 -138.5(2) . . . . ?
C5 C6 C7 C12 104.0(3) . . . . ?
O1 C6 C7 C8 44.1(3) . . . . ?
C5 C6 C7 C8 -73.4(3) . . . . ?
C13 O5 C9 C8 -179.1(2) . . . . ?
C13 O5 C9 C10 -0.7(3) . . . . ?
O5 C9 C8 C7 178.8(2) . . . . ?
C10 C9 C8 C7 0.6(3) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C9 176.3(2) . . . . ?
C13 O4 C10 C11 179.5(3) . . . . ?
C13 O4 C10 C9 1.8(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
O5 C9 C10 C11 -178.6(2) . . . . ?
C8 C9 C10 O4 177.8(2) . . . . ?
O5 C9 C10 O4 -0.7(3) . . . . ?
O4 C10 C11 C12 -177.4(2) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C8 C7 C12 C11 1.1(4) . . . . ?
C6 C7 C12 C11 -176.3(2) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C10 O4 C13 O5 -2.2(3) . . . . ?
C9 O5 C13 O4 1.8(3) . . . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.072

