# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_20181228PKU_LJH1164_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1912652'
loop_
_audit_author_name
_audit_author_address
'Yue Zhao'
;Nanjing University
China
;
_audit_update_record             
;
2019-04-28 deposited with the CCDC.	2019-08-05 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         ?
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.31

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      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                   6.2462(5)
_cell_length_b                   7.5477(6)
_cell_length_c                   31.123(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1467.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3173
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.33

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.985
_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      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            10723
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.618
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2587
_reflns_number_gt                2023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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)+(0.0435P)²+0.1924P] 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 679 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(8)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         2587
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.4446(7) 0.4940(5) 0.62631(10) 0.0471(11) Uani 1 1 d . . . . .
H1A H 0.421971 0.620662 0.621073 0.071 Uiso 1 1 calc R U . . .
H1B H 0.460072 0.473277 0.657239 0.071 Uiso 1 1 calc R U . . .
H1C H 0.321560 0.426971 0.615465 0.071 Uiso 1 1 calc R U . . .
C2 C 0.6380(6) 0.4583(4) 0.56108(10) 0.0303(8) Uani 1 1 d . . . . .
C3 C 0.4780(6) 0.5289(4) 0.53668(10) 0.0285(8) Uani 1 1 d . . . . .
H3 H 0.351456 0.572165 0.549959 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5013(6) 0.5375(4) 0.49135(9) 0.0239(8) Uani 1 1 d . . . . .
C5 C 0.3369(6) 0.6033(4) 0.46464(10) 0.0294(8) Uani 1 1 d . . . . .
H5 H 0.210230 0.649169 0.477367 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3556(6) 0.6025(4) 0.42099(10) 0.0301(8) Uani 1 1 d . . . . .
H6 H 0.240730 0.645297 0.403875 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5442(6) 0.5387(4) 0.40072(9) 0.0243(8) Uani 1 1 d . . . . .
C8 C 0.7080(6) 0.4769(4) 0.42602(9) 0.0262(8) Uani 1 1 d . . . . .
H8 H 0.835702 0.435319 0.412848 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6902(5) 0.4740(4) 0.47180(10) 0.0247(8) Uani 1 1 d . . . . .
C10 C 0.8533(6) 0.4035(4) 0.49814(10) 0.0283(8) Uani 1 1 d . . . . .
H10 H 0.981651 0.360717 0.485460 0.034 Uiso 1 1 calc R U . . .
C11 C 0.8282(6) 0.3963(4) 0.54166(10) 0.0317(9) Uani 1 1 d . . . . .
H11 H 0.939559 0.349216 0.559036 0.038 Uiso 1 1 calc R U . . .
C12 C 0.5491(6) 0.5328(4) 0.35173(9) 0.0272(8) Uani 1 1 d . . . . .
C13 C 0.7703(6) 0.4938(4) 0.33426(9) 0.0268(8) Uani 1 1 d . . . . .
C14 C 0.5504(7) 0.2750(4) 0.30420(10) 0.0369(9) Uani 1 1 d . . . . .
C15 C 0.4115(6) 0.3760(5) 0.33426(10) 0.0376(9) Uani 1 1 d . . . . .
H15A H 0.363776 0.299044 0.358185 0.045 Uiso 1 1 calc R U . . .
H15B H 0.283446 0.421364 0.319076 0.045 Uiso 1 1 calc R U . . .
C16 C 0.4801(6) 0.7088(4) 0.33161(10) 0.0386(9) Uani 1 1 d . . . . .
H16A H 0.574743 0.803685 0.341711 0.058 Uiso 1 1 calc R U . . .
H16B H 0.332350 0.735365 0.339997 0.058 Uiso 1 1 calc R U . . .
H16C H 0.489213 0.700184 0.300247 0.058 Uiso 1 1 calc R U . . .
C17 C 0.9666(7) 0.3792(5) 0.24614(10) 0.0429(10) Uani 1 1 d . . . . .
H17A H 0.831164 0.396734 0.230831 0.064 Uiso 1 1 calc R U . . .
H17B H 1.065591 0.312024 0.227927 0.064 Uiso 1 1 calc R U . . .
H17C H 1.029672 0.494665 0.253030 0.064 Uiso 1 1 calc R U . . .
N1 N 0.7527(5) 0.3515(3) 0.30679(8) 0.0281(7) Uani 1 1 d . . . . .
O1 O 0.6332(4) 0.4376(3) 0.60479(7) 0.0425(7) Uani 1 1 d . . . . .
O2 O 0.9367(4) 0.5748(3) 0.33982(7) 0.0368(6) Uani 1 1 d . . . . .
O3 O 0.9276(4) 0.2824(3) 0.28529(7) 0.0394(7) Uani 1 1 d . . . . .
O4 O 0.5092(5) 0.1490(3) 0.28166(8) 0.0542(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 O1 1.421(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.363(5) . ?
C2 O1 1.370(4) . ?
C2 C11 1.413(5) . ?
C3 C4 1.420(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.411(4) . ?
C4 C5 1.412(4) . ?
C5 C6 1.363(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.421(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(4) . ?
C7 C12 1.526(4) . ?
C8 C9 1.429(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.412(4) . ?
C10 C11 1.364(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.514(5) . ?
C12 C16 1.531(4) . ?
C12 C15 1.561(5) . ?
C13 O2 1.218(4) . ?
C13 N1 1.377(4) . ?
C14 O4 1.209(4) . ?
C14 N1 1.392(5) . ?
C14 C15 1.486(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O3 1.441(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 O3 1.383(4) . ?

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
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 O1 125.6(3) . . ?
C3 C2 C11 120.5(3) . . ?
O1 C2 C11 113.9(3) . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C9 C4 C5 118.3(3) . . ?
C9 C4 C3 119.9(3) . . ?
C5 C4 C3 121.8(3) . . ?
C6 C5 C4 121.5(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 118.6(3) . . ?
C8 C7 C12 123.3(3) . . ?
C6 C7 C12 118.0(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C10 118.7(3) . . ?
C4 C9 C8 119.3(3) . . ?
C10 C9 C8 121.9(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C2 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C2 C11 H11 119.7 . . ?
C13 C12 C7 112.5(3) . . ?
C13 C12 C16 106.2(3) . . ?
C7 C12 C16 112.2(3) . . ?
C13 C12 C15 103.3(3) . . ?
C7 C12 C15 111.1(3) . . ?
C16 C12 C15 111.2(3) . . ?
O2 C13 N1 123.2(3) . . ?
O2 C13 C12 129.1(3) . . ?
N1 C13 C12 107.5(3) . . ?
O4 C14 N1 123.6(4) . . ?
O4 C14 C15 130.1(4) . . ?
N1 C14 C15 106.3(3) . . ?
C14 C15 C12 106.7(3) . . ?
C14 C15 H15A 110.4 . . ?
C12 C15 H15A 110.4 . . ?
C14 C15 H15B 110.4 . . ?
C12 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 O3 122.1(3) . . ?
C13 N1 C14 115.6(3) . . ?
O3 N1 C14 122.2(2) . . ?
C2 O1 C1 116.9(3) . . ?
N1 O3 C17 110.6(3) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039

