# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3az
_database_code_depnum_ccdc_archive 'CCDC 1958966'
loop_
_audit_author_name
_audit_author_address
'wei yongsheng'
;Kyoto
China
;
_audit_update_record             
;
2019-10-12 deposited with the CCDC.	2020-05-08 downloaded from the CCDC.
;
_audit_creation_date             2019-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H17 N O6'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.30
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   8.1801(8)
_cell_length_b                   11.5319(9)
_cell_length_c                   16.4021(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1547.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    788
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.3780
_cell_measurement_theta_min      5.4060
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.8930
_exptl_absorpt_correction_T_min  0.7170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 1.001
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3340
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         64.986
_diffrn_reflns_theta_min         4.687
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.522
_reflns_Friedel_fraction_full    0.687
_reflns_Friedel_fraction_max     0.726
_reflns_number_gt                1885
_reflns_number_total             2339
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       0.0038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0501
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0394P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1163
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N1 N 0.1728(6) 0.4020(3) 0.0220(2) 0.0317(10) Uani 1 1 d . . . . .
O1 O 0.5905(4) 0.5089(2) 0.15547(17) 0.0244(8) Uani 1 1 d . . . . .
O2 O 0.6700(4) 0.6583(2) 0.2321(2) 0.0306(8) Uani 1 1 d . . . . .
O3 O 0.6632(4) 0.3860(3) 0.41824(17) 0.0313(8) Uani 1 1 d . . . . .
O4 O 0.7179(4) 0.5762(3) 0.40553(19) 0.0340(9) Uani 1 1 d . . . . .
O5 O 0.0736(5) 0.3356(3) 0.0514(2) 0.0401(9) Uani 1 1 d . . . . .
O6 O 0.1430(5) 0.4747(3) -0.0307(2) 0.0487(11) Uani 1 1 d . . . . .
C1 C 0.6340(6) 0.5590(4) 0.2282(3) 0.0246(11) Uani 1 1 d . . . . .
C2 C 0.6216(6) 0.4678(4) 0.2917(3) 0.0238(10) Uani 1 1 d . . . . .
C3 C 0.5628(6) 0.3724(4) 0.2580(3) 0.0235(10) Uani 1 1 d . . . . .
H3 H 0.5390 0.3044 0.2861 0.028 Uiso 1 1 calc R . . . .
C4 C 0.5400(6) 0.3891(4) 0.1684(3) 0.0232(11) Uani 1 1 d . . . . .
C5 C 0.6706(6) 0.4860(4) 0.3780(3) 0.0276(11) Uani 1 1 d . . . . .
C6 C 0.7062(7) 0.3906(4) 0.5042(3) 0.0365(13) Uani 1 1 d . . . . .
H6A H 0.6420 0.4495 0.5316 0.044 Uiso 1 1 calc R . . . .
H6B H 0.8210 0.4096 0.5104 0.044 Uiso 1 1 calc R . . . .
C7 C 0.6719(9) 0.2742(4) 0.5400(3) 0.0540(18) Uani 1 1 d . . . . .
H7A H 0.5576 0.2569 0.5346 0.081 Uiso 1 1 calc GR . . . .
H7B H 0.7013 0.2743 0.5967 0.081 Uiso 1 1 calc GR . . . .
H7C H 0.7347 0.2164 0.5118 0.081 Uiso 1 1 calc GR . . . .
C8 C 0.6559(6) 0.3109(4) 0.1203(3) 0.0284(11) Uani 1 1 d . . . . .
H8A H 0.6513 0.3311 0.0635 0.043 Uiso 1 1 calc GR . . . .
H8B H 0.6237 0.2314 0.1270 0.043 Uiso 1 1 calc GR . . . .
H8C H 0.7655 0.3210 0.1400 0.043 Uiso 1 1 calc GR . . . .
C9 C 0.3473(6) 0.3948(4) 0.0497(3) 0.0284(11) Uani 1 1 d . . . . .
H9A H 0.4042 0.4653 0.0344 0.034 Uiso 1 1 calc R . . . .
H9B H 0.4006 0.3302 0.0226 0.034 Uiso 1 1 calc R . . . .
C10 C 0.3581(6) 0.3783(4) 0.1422(3) 0.0239(10) Uani 1 1 d . . . . .
H10 H 0.3226 0.2991 0.1544 0.029 Uiso 1 1 calc R . . . .
C11 C 0.2495(6) 0.4599(4) 0.1895(3) 0.0233(11) Uani 1 1 d . . . . .
C12 C 0.2319(6) 0.5768(4) 0.1691(3) 0.0286(11) Uani 1 1 d . . . . .
H12 H 0.2870 0.6064 0.1241 0.034 Uiso 1 1 calc R . . . .
C13 C 0.1333(6) 0.6493(4) 0.2152(3) 0.0339(13) Uani 1 1 d . . . . .
H13 H 0.1215 0.7266 0.2002 0.041 Uiso 1 1 calc R . . . .
C14 C 0.0523(6) 0.6078(4) 0.2833(3) 0.0332(12) Uani 1 1 d . . . . .
H14 H -0.0131 0.6566 0.3145 0.040 Uiso 1 1 calc R . . . .
C15 C 0.0706(6) 0.4920(4) 0.3041(3) 0.0319(12) Uani 1 1 d . . . . .
H15 H 0.0174 0.4629 0.3499 0.038 Uiso 1 1 calc R . . . .
C16 C 0.1665(6) 0.4202(4) 0.2578(3) 0.0295(11) Uani 1 1 d . . . . .
H16 H 0.1762 0.3426 0.2725 0.035 Uiso 1 1 calc R . . . .


_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
N1 O5 1.215(5) . ?
N1 O6 1.229(5) . ?
N1 C9 1.501(6) . ?
O1 C1 1.372(5) . ?
O1 C4 1.457(5) . ?
O2 C1 1.184(5) . ?
O3 C5 1.331(5) . ?
O3 C6 1.454(5) . ?
O4 C5 1.198(5) . ?
C1 C2 1.484(6) . ?
C2 C3 1.321(6) . ?
C2 C5 1.486(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.493(6) . ?
C4 C8 1.528(6) . ?
C4 C10 1.554(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.492(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.531(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.509(6) . ?
C11 C12 1.396(6) . ?
C11 C16 1.388(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(6) . ?
C16 H16 0.9300 . ?

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
O5 N1 O6 125.2(5) . . ?
O5 N1 C9 118.7(4) . . ?
O6 N1 C9 116.1(4) . . ?
C1 O1 C4 110.2(3) . . ?
C5 O3 C6 116.0(4) . . ?
O1 C1 C2 107.1(4) . . ?
O2 C1 O1 121.2(4) . . ?
O2 C1 C2 131.7(5) . . ?
C1 C2 C5 123.3(4) . . ?
C3 C2 C1 108.7(4) . . ?
C3 C2 C5 127.9(4) . . ?
C2 C3 H3 124.8 . . ?
C2 C3 C4 110.5(4) . . ?
C4 C3 H3 124.8 . . ?
O1 C4 C3 103.3(4) . . ?
O1 C4 C8 108.0(4) . . ?
O1 C4 C10 107.8(4) . . ?
C3 C4 C8 110.8(4) . . ?
C3 C4 C10 112.4(4) . . ?
C8 C4 C10 113.8(4) . . ?
O3 C5 C2 109.7(4) . . ?
O4 C5 O3 125.4(4) . . ?
O4 C5 C2 124.7(4) . . ?
O3 C6 H6A 110.2 . . ?
O3 C6 H6B 110.2 . . ?
O3 C6 C7 107.7(4) . . ?
H6A C6 H6B 108.5 . . ?
C7 C6 H6A 110.2 . . ?
C7 C6 H6B 110.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
N1 C9 C10 111.2(4) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C4 C10 H10 107.5 . . ?
C9 C10 C4 108.7(4) . . ?
C9 C10 H10 107.5 . . ?
C11 C10 C4 111.8(4) . . ?
C11 C10 C9 113.5(4) . . ?
C11 C10 H10 107.5 . . ?
C12 C11 C10 122.7(4) . . ?
C16 C11 C10 119.8(4) . . ?
C16 C11 C12 117.5(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(5) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.7(5) . . ?
C15 C14 H14 120.7 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.1 . . ?
C15 C16 C11 121.9(4) . . ?
C15 C16 H16 119.1 . . ?

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
N1 C9 C10 C4 -172.1(4) . . . . ?
N1 C9 C10 C11 -47.0(5) . . . . ?
O1 C1 C2 C3 -4.2(5) . . . . ?
O1 C1 C2 C5 175.4(4) . . . . ?
O1 C4 C10 C9 67.6(4) . . . . ?
O1 C4 C10 C11 -58.4(4) . . . . ?
O2 C1 C2 C3 174.6(5) . . . . ?
O2 C1 C2 C5 -5.8(9) . . . . ?
O5 N1 C9 C10 -42.1(6) . . . . ?
O6 N1 C9 C10 139.2(4) . . . . ?
C1 O1 C4 C3 -1.4(5) . . . . ?
C1 O1 C4 C8 -118.8(4) . . . . ?
C1 O1 C4 C10 117.8(4) . . . . ?
C1 C2 C3 C4 3.3(5) . . . . ?
C1 C2 C5 O3 -173.0(4) . . . . ?
C1 C2 C5 O4 3.3(8) . . . . ?
C2 C3 C4 O1 -1.3(5) . . . . ?
C2 C3 C4 C8 114.1(5) . . . . ?
C2 C3 C4 C10 -117.3(4) . . . . ?
C3 C2 C5 O3 6.4(7) . . . . ?
C3 C2 C5 O4 -177.2(5) . . . . ?
C3 C4 C10 C9 -179.1(4) . . . . ?
C3 C4 C10 C11 54.9(5) . . . . ?
C4 O1 C1 O2 -175.6(4) . . . . ?
C4 O1 C1 C2 3.3(5) . . . . ?
C4 C10 C11 C12 81.7(5) . . . . ?
C4 C10 C11 C16 -96.1(5) . . . . ?
C5 O3 C6 C7 173.5(5) . . . . ?
C5 C2 C3 C4 -176.2(5) . . . . ?
C6 O3 C5 O4 4.4(8) . . . . ?
C6 O3 C5 C2 -179.3(4) . . . . ?
C8 C4 C10 C9 -52.1(5) . . . . ?
C8 C4 C10 C11 -178.1(4) . . . . ?
C9 C10 C11 C12 -41.7(6) . . . . ?
C9 C10 C11 C16 140.5(4) . . . . ?
C10 C11 C12 C13 -178.7(4) . . . . ?
C10 C11 C16 C15 177.9(4) . . . . ?
C11 C12 C13 C14 1.1(8) . . . . ?
C12 C11 C16 C15 -0.1(7) . . . . ?
C12 C13 C14 C15 -0.5(7) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
C14 C15 C16 C11 0.6(8) . . . . ?
C16 C11 C12 C13 -0.8(7) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
