# 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_zhaoyl190304_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1940266'
loop_
_audit_author_name
_audit_author_address
A
;Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2019-07-13 deposited with the CCDC.	2019-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N O6'
_chemical_formula_weight         367.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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                   7.524(7)
_cell_length_b                   14.474(13)
_cell_length_c                   16.108(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.52(3)
_cell_angle_gamma                90
_cell_volume                     1754(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3350
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      24.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            10742
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.052
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             3052
_reflns_number_gt                2623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.974
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.954

_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)+(0.0389P)²+0.3945P] 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       0.0163(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1147 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3052
_refine_ls_number_parameters     247
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.039
_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
C1 C -0.1736(5) 0.9275(2) 0.3822(3) 0.0512(9) Uani 1 1 d . . . . .
H1 H -0.1701 0.9691 0.3383 0.061 Uiso 1 1 calc R U . . .
C2 C -0.3129(5) 0.9277(3) 0.4317(3) 0.0558(10) Uani 1 1 d . . . . .
H2 H -0.4046 0.9699 0.4227 0.067 Uiso 1 1 calc R U . . .
C3 C -0.3214(5) 0.8645(3) 0.4971(3) 0.0533(10) Uani 1 1 d . . . . .
H3 H -0.4191 0.8651 0.5313 0.064 Uiso 1 1 calc R U . . .
C4 C -0.1883(4) 0.8020(3) 0.5115(2) 0.0450(9) Uani 1 1 d . . . . .
H4 H -0.1962 0.7600 0.5550 0.054 Uiso 1 1 calc R U . . .
C5 C -0.0404(4) 0.8011(2) 0.46107(19) 0.0350(7) Uani 1 1 d . . . . .
C6 C -0.0301(4) 0.8646(2) 0.3956(2) 0.0387(8) Uani 1 1 d . . . . .
C7 C 0.1206(5) 0.8659(2) 0.3471(2) 0.0493(9) Uani 1 1 d . . . . .
H7 H 0.1267 0.9072 0.3031 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2583(5) 0.8078(2) 0.3632(2) 0.0451(8) Uani 1 1 d . . . . .
H8 H 0.3593 0.8112 0.3313 0.054 Uiso 1 1 calc R U . . .
C9 C 0.2504(4) 0.7419(2) 0.42821(19) 0.0335(7) Uani 1 1 d . . . . .
C10 C 0.1033(4) 0.7385(2) 0.47501(19) 0.0346(7) Uani 1 1 d . . . . .
H10 H 0.0962 0.6946 0.5169 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4008(4) 0.6787(2) 0.44311(18) 0.0302(7) Uani 1 1 d . . . . .
C12 C 0.5463(4) 0.6665(2) 0.40021(18) 0.0325(7) Uani 1 1 d . . . . .
C13 C 0.6668(4) 0.5970(2) 0.4387(2) 0.0363(7) Uani 1 1 d . . . . .
C14 C 0.4212(4) 0.6143(2) 0.5161(2) 0.0360(7) Uani 1 1 d . . . . .
C15 C 0.6501(4) 0.4974(2) 0.5631(2) 0.0400(8) Uani 1 1 d . . . . .
H15A H 0.6939 0.4466 0.5302 0.048 Uiso 1 1 calc R U . . .
H15B H 0.5541 0.4741 0.5962 0.048 Uiso 1 1 calc R U . . .
C16 C 0.7973(4) 0.5311(2) 0.6202(2) 0.0389(8) Uani 1 1 d . . . . .
C17 C 1.0309(5) 0.4793(3) 0.7099(3) 0.0584(10) Uani 1 1 d . . . . .
H17A H 0.9844 0.5165 0.7545 0.070 Uiso 1 1 calc R U . . .
H17B H 1.1271 0.5131 0.6849 0.070 Uiso 1 1 calc R U . . .
C18 C 1.0963(5) 0.3903(3) 0.7426(3) 0.0657(12) Uani 1 1 d . . . . .
H18A H 1.0062 0.3622 0.7753 0.099 Uiso 1 1 calc R U . . .
H18B H 1.2012 0.4003 0.7766 0.099 Uiso 1 1 calc R U . . .
H18C H 1.1241 0.3503 0.6972 0.099 Uiso 1 1 calc R U . . .
C19 C 0.6065(4) 0.6714(3) 0.2587(2) 0.0399(8) Uani 1 1 d . . . . .
C20 C 0.6734(6) 0.7355(3) 0.1958(2) 0.0617(11) Uani 1 1 d . . . . .
H20A H 0.7076 0.7013 0.1477 0.093 Uiso 1 1 calc R U . . .
H20B H 0.7745 0.7683 0.2183 0.093 Uiso 1 1 calc R U . . .
H20C H 0.5816 0.7788 0.1803 0.093 Uiso 1 1 calc R U . . .
N1 N 0.5817(3) 0.56779(18) 0.50846(16) 0.0379(6) Uani 1 1 d . . . . .
O1 O 0.8232(4) 0.60928(18) 0.63887(19) 0.0669(8) Uani 1 1 d . . . . .
O2 O 0.8916(3) 0.46039(15) 0.64811(14) 0.0433(6) Uani 1 1 d . . . . .
O3 O 0.3242(3) 0.60255(17) 0.57253(15) 0.0531(7) Uani 1 1 d . . . . .
O4 O 0.8080(3) 0.57095(17) 0.41640(15) 0.0497(7) Uani 1 1 d . . . . .
O5 O 0.5598(4) 0.5940(2) 0.25041(16) 0.0582(7) Uani 1 1 d . . . . .
O6 O 0.6009(3) 0.71568(15) 0.33341(14) 0.0409(6) 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 1.334(6) . ?
C1 C6 1.425(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(4) . ?
C5 C10 1.424(4) . ?
C6 C7 1.393(5) . ?
C7 C8 1.354(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.419(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.357(4) . ?
C9 C11 1.469(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.322(4) . ?
C11 C14 1.505(4) . ?
C12 O6 1.363(4) . ?
C12 C13 1.479(4) . ?
C13 O4 1.191(4) . ?
C13 N1 1.375(4) . ?
C14 O3 1.193(4) . ?
C14 N1 1.391(4) . ?
C15 N1 1.433(4) . ?
C15 C16 1.502(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.186(4) . ?
C16 O2 1.317(4) . ?
C17 O2 1.452(4) . ?
C17 C18 1.472(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O5 1.181(4) . ?
C19 O6 1.365(4) . ?
C19 C20 1.473(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 C6 121.0(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C10 121.9(3) . . ?
C6 C5 C10 118.6(3) . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 C1 122.1(3) . . ?
C5 C6 C1 118.4(3) . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 119.0(3) . . ?
C10 C9 C11 121.5(3) . . ?
C8 C9 C11 119.5(3) . . ?
C9 C10 C5 121.1(3) . . ?
C9 C10 H10 119.4 . . ?
C5 C10 H10 119.4 . . ?
C12 C11 C9 130.0(3) . . ?
C12 C11 C14 104.9(3) . . ?
C9 C11 C14 125.1(3) . . ?
C11 C12 O6 127.9(3) . . ?
C11 C12 C13 112.3(3) . . ?
O6 C12 C13 119.4(3) . . ?
O4 C13 N1 125.9(3) . . ?
O4 C13 C12 129.1(3) . . ?
N1 C13 C12 104.9(3) . . ?
O3 C14 N1 123.3(3) . . ?
O3 C14 C11 129.2(3) . . ?
N1 C14 C11 107.5(2) . . ?
N1 C15 C16 113.1(3) . . ?
N1 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
N1 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
O1 C16 O2 124.8(3) . . ?
O1 C16 C15 125.3(3) . . ?
O2 C16 C15 109.8(3) . . ?
O2 C17 C18 107.9(3) . . ?
O2 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O2 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 O6 122.0(3) . . ?
O5 C19 C20 128.8(3) . . ?
O6 C19 C20 109.2(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 N1 C14 110.3(2) . . ?
C13 N1 C15 123.6(3) . . ?
C14 N1 C15 126.0(3) . . ?
C16 O2 C17 117.4(3) . . ?
C12 O6 C19 117.9(2) . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.035

_shelxl_version_number           2014-3

