# 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_cu_20180821RS1_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc21tncx
_database_code_depnum_ccdc_archive 'CCDC 1901489'
loop_
_audit_author_name
_audit_author_address
'Sai Ruan'
;Sichuan University
China
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2020-01-13 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         ?
_chemical_formula_sum            'C20 H16 N2 O4'
_chemical_formula_weight         348.35

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                   9.9589(2)
_cell_length_b                   10.3374(2)
_cell_length_c                   17.3428(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1785.43(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    241(2)
_cell_measurement_reflns_used    9179
_cell_measurement_theta_min      4.98
_cell_measurement_theta_max      68.25

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.755
_shelx_estimated_absorpt_T_min   0.752
_shelx_estimated_absorpt_T_max   0.805
_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      241(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            10924
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.980
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3220
_reflns_number_gt                3154
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.987

_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)+(0.0687P)²+0.1095P] 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 1333 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         3220
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.010
_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 0.54457(19) 0.29946(14) 0.57101(8) 0.0636(4) Uani 1 1 d . . . . .
N1 N 0.45327(15) 0.49747(13) 0.54137(8) 0.0443(3) Uani 1 1 d . . . . .
C1 C 0.4208(3) 0.5453(3) 0.67710(14) 0.0683(6) Uani 1 1 d . . . . .
H1 H 0.347780 0.487745 0.678289 0.082 Uiso 1 1 calc R U . . .
O2 O 0.34058(18) 0.66388(13) 0.48197(10) 0.0634(4) Uani 1 1 d . . . . .
N2 N 0.7309(2) 0.3923(2) 0.39665(14) 0.0758(6) Uani 1 1 d . . . . .
C2 C 0.4593(4) 0.6118(4) 0.74280(15) 0.0894(9) Uani 1 1 d . . . . .
H2 H 0.413110 0.597564 0.789291 0.107 Uiso 1 1 calc R U . . .
C3 C 0.5630(4) 0.6972(3) 0.74103(17) 0.0894(9) Uani 1 1 d . . . . .
H3 H 0.587773 0.741731 0.786072 0.107 Uiso 1 1 calc R U . . .
O3 O 0.44849(15) 0.06364(13) 0.47144(9) 0.0579(4) Uani 1 1 d . . . . .
O4 O 0.66610(16) 0.08290(17) 0.44118(12) 0.0726(5) Uani 1 1 d . . . . .
C4 C 0.6311(4) 0.7183(3) 0.6739(2) 0.0897(9) Uani 1 1 d . . . . .
H4 H 0.701786 0.778554 0.672722 0.108 Uiso 1 1 calc R U . . .
C5 C 0.5967(3) 0.6516(2) 0.60738(14) 0.0665(6) Uani 1 1 d . . . . .
H5 H 0.644279 0.665040 0.561270 0.080 Uiso 1 1 calc R U . . .
C6 C 0.49150(18) 0.56533(16) 0.61015(10) 0.0452(4) Uani 1 1 d . . . . .
C7 C 0.37971(19) 0.55406(17) 0.48179(11) 0.0470(4) Uani 1 1 d . . . . .
C8 C 0.3634(2) 0.45527(18) 0.41885(11) 0.0537(4) Uani 1 1 d . . . . .
H8A H 0.417517 0.478552 0.373737 0.064 Uiso 1 1 calc R U . . .
H8B H 0.269142 0.448533 0.403145 0.064 Uiso 1 1 calc R U . . .
C9 C 0.41213(17) 0.32808(16) 0.45378(10) 0.0443(4) Uani 1 1 d . . . . .
H9 H 0.333555 0.272602 0.465141 0.053 Uiso 1 1 calc R U . . .
C10 C 0.47844(19) 0.36750(16) 0.52932(10) 0.0453(4) Uani 1 1 d . . . . .
C11 C 0.6379(2) 0.32784(19) 0.39798(12) 0.0529(4) Uani 1 1 d . . . . .
C12 C 0.51297(17) 0.25107(16) 0.40295(10) 0.0437(4) Uani 1 1 d . . . . .
C13 C 0.55318(19) 0.12207(17) 0.44118(11) 0.0474(4) Uani 1 1 d . . . . .
C14 C 0.4751(3) -0.0528(2) 0.51521(17) 0.0726(6) Uani 1 1 d . . . . .
H14A H 0.397813 -0.109638 0.512539 0.109 Uiso 1 1 calc R U . . .
H14B H 0.492565 -0.030197 0.568570 0.109 Uiso 1 1 calc R U . . .
H14C H 0.552902 -0.096452 0.493857 0.109 Uiso 1 1 calc R U . . .
C15 C 0.3392(2) 0.1541(2) 0.31375(15) 0.0674(5) Uani 1 1 d . . . . .
H15 H 0.298035 0.117103 0.357240 0.081 Uiso 1 1 calc R U . . .
C16 C 0.4541(2) 0.22719(18) 0.32211(11) 0.0502(4) Uani 1 1 d . . . . .
C17 C 0.5129(4) 0.2801(3) 0.25779(15) 0.0821(8) Uani 1 1 d . . . . .
H17 H 0.592173 0.328770 0.262502 0.098 Uiso 1 1 calc R U . . .
C18 C 0.4551(5) 0.2616(4) 0.18590(17) 0.1070(12) Uani 1 1 d . . . . .
H18 H 0.494766 0.299595 0.142245 0.128 Uiso 1 1 calc R U . . .
C19 C 0.3420(4) 0.1894(4) 0.17757(17) 0.0948(10) Uani 1 1 d . . . . .
H19 H 0.303854 0.176944 0.128556 0.114 Uiso 1 1 calc R U . . .
C20 C 0.2846(3) 0.1354(3) 0.2412(2) 0.0869(9) Uani 1 1 d . . . . .
H20 H 0.206760 0.084763 0.235778 0.104 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 C10 1.205(2) . ?
N1 C10 1.383(2) . ?
N1 C7 1.395(2) . ?
N1 C6 1.435(2) . ?
C1 C6 1.374(3) . ?
C1 C2 1.385(4) . ?
C1 H1 0.9400 . ?
O2 C7 1.200(2) . ?
N2 C11 1.141(3) . ?
C2 C3 1.358(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.365(6) . ?
C3 H3 0.9400 . ?
O3 C13 1.314(2) . ?
O3 C14 1.447(3) . ?
O4 C13 1.195(3) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9400 . ?
C7 C8 1.504(3) . ?
C8 C9 1.527(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.523(2) . ?
C9 C12 1.555(2) . ?
C9 H9 0.9900 . ?
C11 C12 1.479(3) . ?
C12 C16 1.540(2) . ?
C12 C13 1.542(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.378(3) . ?
C15 C20 1.384(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.373(4) . ?
C17 C18 1.386(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.359(6) . ?
C18 H18 0.9400 . ?
C19 C20 1.363(6) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?

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
C10 N1 C7 112.99(15) . . ?
C10 N1 C6 123.54(15) . . ?
C7 N1 C6 123.36(14) . . ?
C6 C1 C2 118.6(3) . . ?
C6 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C13 O3 C14 116.49(17) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C1 C6 C5 121.14(19) . . ?
C1 C6 N1 119.53(18) . . ?
C5 C6 N1 119.31(17) . . ?
O2 C7 N1 124.41(17) . . ?
O2 C7 C8 127.53(17) . . ?
N1 C7 C8 108.04(14) . . ?
C7 C8 C9 105.22(14) . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C10 C9 C8 104.40(13) . . ?
C10 C9 C12 110.16(14) . . ?
C8 C9 C12 114.90(15) . . ?
C10 C9 H9 109.1 . . ?
C8 C9 H9 109.1 . . ?
C12 C9 H9 109.1 . . ?
O1 C10 N1 125.15(17) . . ?
O1 C10 C9 126.67(16) . . ?
N1 C10 C9 108.15(14) . . ?
N2 C11 C12 176.1(2) . . ?
C11 C12 C16 110.71(15) . . ?
C11 C12 C13 105.70(15) . . ?
C16 C12 C13 110.59(14) . . ?
C11 C12 C9 107.57(15) . . ?
C16 C12 C9 110.62(14) . . ?
C13 C12 C9 111.50(14) . . ?
O4 C13 O3 126.21(18) . . ?
O4 C13 C12 122.50(18) . . ?
O3 C13 C12 111.29(15) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 119.9(3) . . ?
C16 C15 H15 120.1 . . ?
C20 C15 H15 120.1 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 C12 120.9(2) . . ?
C15 C16 C12 119.98(19) . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C18 119.1(3) . . ?
C20 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.5 . . ?
C15 C20 H20 119.5 . . ?

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
C6 C1 C2 C3 1.4(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C2 C1 C6 C5 -1.5(4) . . . . ?
C2 C1 C6 N1 -180.0(2) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C4 C5 C6 N1 178.8(2) . . . . ?
C10 N1 C6 C1 -74.2(2) . . . . ?
C7 N1 C6 C1 101.8(2) . . . . ?
C10 N1 C6 C5 107.3(2) . . . . ?
C7 N1 C6 C5 -76.7(2) . . . . ?
C10 N1 C7 O2 176.0(2) . . . . ?
C6 N1 C7 O2 -0.4(3) . . . . ?
C10 N1 C7 C8 -5.6(2) . . . . ?
C6 N1 C7 C8 178.02(17) . . . . ?
O2 C7 C8 C9 -171.5(2) . . . . ?
N1 C7 C8 C9 10.2(2) . . . . ?
C7 C8 C9 C10 -10.6(2) . . . . ?
C7 C8 C9 C12 -131.40(16) . . . . ?
C7 N1 C10 O1 176.8(2) . . . . ?
C6 N1 C10 O1 -6.9(3) . . . . ?
C7 N1 C10 C9 -1.5(2) . . . . ?
C6 N1 C10 C9 174.84(16) . . . . ?
C8 C9 C10 O1 -170.5(2) . . . . ?
C12 C9 C10 O1 -46.6(3) . . . . ?
C8 C9 C10 N1 7.77(19) . . . . ?
C12 C9 C10 N1 131.64(15) . . . . ?
C10 C9 C12 C11 -51.05(18) . . . . ?
C8 C9 C12 C11 66.49(19) . . . . ?
C10 C9 C12 C16 -172.08(15) . . . . ?
C8 C9 C12 C16 -54.5(2) . . . . ?
C10 C9 C12 C13 64.40(18) . . . . ?
C8 C9 C12 C13 -178.05(15) . . . . ?
C14 O3 C13 O4 6.4(3) . . . . ?
C14 O3 C13 C12 -174.51(18) . . . . ?
C11 C12 C13 O4 -21.5(3) . . . . ?
C16 C12 C13 O4 98.4(2) . . . . ?
C9 C12 C13 O4 -138.1(2) . . . . ?
C11 C12 C13 O3 159.37(16) . . . . ?
C16 C12 C13 O3 -80.77(19) . . . . ?
C9 C12 C13 O3 42.8(2) . . . . ?
C20 C15 C16 C17 -0.2(4) . . . . ?
C20 C15 C16 C12 178.4(2) . . . . ?
C11 C12 C16 C17 -3.2(3) . . . . ?
C13 C12 C16 C17 -120.1(2) . . . . ?
C9 C12 C16 C17 115.9(2) . . . . ?
C11 C12 C16 C15 178.17(19) . . . . ?
C13 C12 C16 C15 61.4(2) . . . . ?
C9 C12 C16 C15 -62.7(2) . . . . ?
C15 C16 C17 C18 1.2(5) . . . . ?
C12 C16 C17 C18 -177.4(3) . . . . ?
C16 C17 C18 C19 -1.3(6) . . . . ?
C17 C18 C19 C20 0.4(6) . . . . ?
C18 C19 C20 C15 0.6(5) . . . . ?
C16 C15 C20 C19 -0.7(4) . . . . ?

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
C14 H14A O2 0.97 2.47 3.272(3) 140.3 1_545

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.058

