# 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. 
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#######################################################################

data_zhaoyl191120_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1968020'
loop_
_audit_author_name
_audit_author_address
' Zhan-Gang Han'
;Faculty of Chemistry, Northeast Normal University
China
;
_audit_update_record             
;
2019-11-26 deposited with the CCDC.	2020-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 N O8'
_chemical_formula_weight         467.46

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   11.712(2)
_cell_length_b                   11.717(2)
_cell_length_c                   17.423(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2390.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9041
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      63.63

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.815
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.898
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12417
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.548
_diffrn_reflns_theta_max         63.797
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.913
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.884
_reflns_number_total             3806
_reflns_number_gt                3391
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.928
_reflns_Friedel_fraction_full    0.852

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0368P)²+0.2351P] 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
_refine_ls_extinction_coef       0.0082(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1459 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3806
_refine_ls_number_parameters     314
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0770
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2905(2) 0.3640(2) 0.41808(16) 0.0364(6) Uani 1 1 d . . . . .
C2 C 0.2615(2) 0.4642(2) 0.38243(15) 0.0356(6) Uani 1 1 d . . . . .
C3 C 0.1789(2) 0.4364(2) 0.32397(15) 0.0342(6) Uani 1 1 d . . . . .
C4 C 0.1611(2) 0.3176(2) 0.32848(15) 0.0342(6) Uani 1 1 d . . . . .
C5 C 0.0813(2) 0.2595(2) 0.28209(15) 0.0368(6) Uani 1 1 d . . . . .
C6 C 0.0268(3) 0.3262(2) 0.22724(15) 0.0376(7) Uani 1 1 d . . . . .
C7 C 0.0459(3) 0.4449(2) 0.22026(16) 0.0405(7) Uani 1 1 d . . . . .
C8 C 0.1218(2) 0.5024(2) 0.26813(17) 0.0406(7) Uani 1 1 d . . . . .
C9 C 0.2470(2) 0.1578(2) 0.40894(16) 0.0360(6) Uani 1 1 d . . . . .
C10 C 0.2094(3) 0.1227(2) 0.47967(17) 0.0457(7) Uani 1 1 d . . . . .
H10 H 0.1736 0.1737 0.5128 0.055 Uiso 1 1 calc R U . . .
C11 C 0.2256(3) 0.0100(3) 0.5009(2) 0.0582(9) Uani 1 1 d . . . . .
H11 H 0.2012 -0.0151 0.5488 0.070 Uiso 1 1 calc R U . . .
C12 C 0.2776(3) -0.0647(3) 0.4514(2) 0.0597(9) Uani 1 1 d . . . . .
H12 H 0.2877 -0.1405 0.4657 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3148(3) -0.0281(3) 0.3811(2) 0.0593(9) Uani 1 1 d . . . . .
H13 H 0.3495 -0.0793 0.3476 0.071 Uiso 1 1 calc R U . . .
C14 C 0.3011(3) 0.0842(3) 0.35972(18) 0.0497(8) Uani 1 1 d . . . . .
H14 H 0.3282 0.1098 0.3126 0.060 Uiso 1 1 calc R U . . .
C15 C 0.0512(3) 0.1354(3) 0.29309(19) 0.0524(8) Uani 1 1 d . . . . .
H15A H 0.1069 0.0886 0.2678 0.079 Uiso 1 1 calc R U . . .
H15B H -0.0229 0.1208 0.2715 0.079 Uiso 1 1 calc R U . . .
H15C H 0.0502 0.1179 0.3469 0.079 Uiso 1 1 calc R U . . .
C16 C -0.0547(2) 0.2694(2) 0.17295(16) 0.0403(7) Uani 1 1 d . . . . .
C17 C -0.0165(3) 0.5098(3) 0.15889(18) 0.0487(8) Uani 1 1 d . . . . .
C18 C 0.1509(3) 0.6270(3) 0.2572(2) 0.0602(9) Uani 1 1 d . . . . .
H18A H 0.0904 0.6636 0.2282 0.072 Uiso 1 1 calc R U . . .
H18B H 0.1553 0.6638 0.3070 0.072 Uiso 1 1 calc R U . . .
C19 C 0.3105(2) 0.5755(2) 0.40563(16) 0.0388(6) Uani 1 1 d . . . . .
C20 C 0.3726(3) 0.3452(2) 0.48167(17) 0.0420(7) Uani 1 1 d . . . . .
C21 C 0.4269(4) 0.4078(4) 0.6050(2) 0.0845(13) Uani 1 1 d . . . . .
H21A H 0.4854 0.4651 0.6020 0.127 Uiso 1 1 calc R U . . .
H21B H 0.4616 0.3336 0.6061 0.127 Uiso 1 1 calc R U . . .
H21C H 0.3831 0.4190 0.6510 0.127 Uiso 1 1 calc R U . . .
C22 C 0.4803(3) 0.6742(3) 0.4329(3) 0.0838(14) Uani 1 1 d . . . . .
H22A H 0.4658 0.6858 0.4865 0.126 Uiso 1 1 calc R U . . .
H22B H 0.4516 0.7381 0.4043 0.126 Uiso 1 1 calc R U . . .
H22C H 0.5610 0.6672 0.4245 0.126 Uiso 1 1 calc R U . . .
C23 C 0.2623(5) 0.6435(4) 0.2157(3) 0.1063(18) Uani 1 1 d . . . . .
H23A H 0.2550 0.6166 0.1639 0.160 Uiso 1 1 calc R U . . .
H23B H 0.3212 0.6013 0.2414 0.160 Uiso 1 1 calc R U . . .
H23C H 0.2817 0.7231 0.2153 0.160 Uiso 1 1 calc R U . . .
C24 C -0.0558(3) 0.5155(4) 0.0261(2) 0.0694(11) Uani 1 1 d . . . . .
H24A H -0.0261 0.5904 0.0159 0.104 Uiso 1 1 calc R U . . .
H24B H -0.1354 0.5209 0.0386 0.104 Uiso 1 1 calc R U . . .
H24C H -0.0463 0.4684 -0.0186 0.104 Uiso 1 1 calc R U . . .
C25 C -0.2375(3) 0.2784(3) 0.1172(2) 0.0626(10) Uani 1 1 d . . . . .
H25A H -0.2554 0.2003 0.1286 0.094 Uiso 1 1 calc R U . . .
H25B H -0.2053 0.2834 0.0667 0.094 Uiso 1 1 calc R U . . .
H25C H -0.3059 0.3234 0.1195 0.094 Uiso 1 1 calc R U . . .
N1 N 0.23131(19) 0.27492(18) 0.38598(13) 0.0371(5) Uani 1 1 d . . . . .
O1 O -0.15621(16) 0.32084(17) 0.17264(11) 0.0464(5) Uani 1 1 d . . . . .
O2 O -0.0328(2) 0.1879(2) 0.13441(13) 0.0609(6) Uani 1 1 d . . . . .
O3 O 0.00564(18) 0.46534(19) 0.09017(12) 0.0503(5) Uani 1 1 d . . . . .
O4 O -0.0775(3) 0.5894(2) 0.16944(18) 0.0881(9) Uani 1 1 d . . . . .
O5 O 0.42372(17) 0.57104(17) 0.40766(15) 0.0559(6) Uani 1 1 d . . . . .
O6 O 0.25580(19) 0.65866(18) 0.42153(15) 0.0580(6) Uani 1 1 d . . . . .
O7 O 0.3525(2) 0.4167(2) 0.53869(12) 0.0608(6) Uani 1 1 d . . . . .
O8 O 0.4480(2) 0.2765(2) 0.48029(16) 0.0747(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.372(4) . ?
C1 N1 1.372(3) . ?
C1 C20 1.484(4) . ?
C2 C3 1.442(4) . ?
C2 C19 1.481(4) . ?
C3 C4 1.409(4) . ?
C3 C8 1.411(4) . ?
C4 N1 1.389(4) . ?
C4 C5 1.411(4) . ?
C5 C6 1.390(4) . ?
C5 C15 1.509(4) . ?
C6 C7 1.413(4) . ?
C6 C16 1.500(4) . ?
C7 C8 1.393(4) . ?
C7 C17 1.502(4) . ?
C8 C18 1.512(4) . ?
C9 C14 1.371(4) . ?
C9 C10 1.372(4) . ?
C9 N1 1.441(3) . ?
C10 C11 1.384(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.369(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O2 1.196(3) . ?
C16 O1 1.333(3) . ?
C17 O4 1.189(4) . ?
C17 O3 1.331(4) . ?
C18 C23 1.503(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 O6 1.199(3) . ?
C19 O5 1.327(3) . ?
C20 O8 1.195(4) . ?
C20 O7 1.320(4) . ?
C21 O7 1.451(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 O5 1.447(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O3 1.453(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 O1 1.444(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C2 C1 N1 110.0(2) . . ?
C2 C1 C20 128.7(2) . . ?
N1 C1 C20 121.3(2) . . ?
C1 C2 C3 107.0(2) . . ?
C1 C2 C19 122.3(2) . . ?
C3 C2 C19 130.7(2) . . ?
C4 C3 C8 120.6(2) . . ?
C4 C3 C2 106.4(2) . . ?
C8 C3 C2 132.9(2) . . ?
N1 C4 C3 108.0(2) . . ?
N1 C4 C5 129.1(2) . . ?
C3 C4 C5 122.8(2) . . ?
C6 C5 C4 115.3(2) . . ?
C6 C5 C15 121.5(3) . . ?
C4 C5 C15 123.2(2) . . ?
C5 C6 C7 122.7(3) . . ?
C5 C6 C16 118.4(2) . . ?
C7 C6 C16 118.9(3) . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 C17 119.5(3) . . ?
C6 C7 C17 118.8(3) . . ?
C7 C8 C3 116.8(3) . . ?
C7 C8 C18 122.4(3) . . ?
C3 C8 C18 120.6(3) . . ?
C14 C9 C10 121.5(3) . . ?
C14 C9 N1 118.9(2) . . ?
C10 C9 N1 119.6(3) . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 119.0(3) . . ?
C9 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 O1 123.4(3) . . ?
O2 C16 C6 124.9(3) . . ?
O1 C16 C6 111.7(2) . . ?
O4 C17 O3 124.3(3) . . ?
O4 C17 C7 125.4(3) . . ?
O3 C17 C7 110.4(2) . . ?
C23 C18 C8 112.4(3) . . ?
C23 C18 H18A 109.1 . . ?
C8 C18 H18A 109.1 . . ?
C23 C18 H18B 109.1 . . ?
C8 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
O6 C19 O5 124.0(3) . . ?
O6 C19 C2 124.9(3) . . ?
O5 C19 C2 111.1(2) . . ?
O8 C20 O7 125.0(3) . . ?
O8 C20 C1 124.3(3) . . ?
O7 C20 C1 110.6(3) . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C4 108.6(2) . . ?
C1 N1 C9 123.1(2) . . ?
C4 N1 C9 128.2(2) . . ?
C16 O1 C25 115.8(2) . . ?
C17 O3 C24 115.9(3) . . ?
C19 O5 C22 115.6(3) . . ?
C20 O7 C21 116.6(3) . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034

_shelxl_version_number           2014-3



