# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Compound3o
_database_code_depnum_ccdc_archive 'CCDC 2067966'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-03-04 deposited with the CCDC.	2021-06-01 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         'C19 H24 N2 O4'
_chemical_formula_sum            'C19 H24 N2 O4'
_chemical_formula_weight         344.40

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.9866(6)
_cell_length_b                   10.4170(6)
_cell_length_c                   10.4938(8)
_cell_angle_alpha                101.921(6)
_cell_angle_beta                 111.131(7)
_cell_angle_gamma                105.454(5)
_cell_volume                     924.17(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3066
_cell_measurement_theta_min      4.6390
_cell_measurement_theta_max      72.5240

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.711
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82699
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            7446
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.677
_diffrn_reflns_theta_max         72.916
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3569
_reflns_number_gt                2924
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0805P)²+1.0122P] 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_number_reflns         3569
_refine_ls_number_parameters     226
_refine_ls_number_restraints     221
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1732
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.204
_refine_ls_shift/su_max          0.001
_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 0.6410(2) 0.55889(18) 0.83643(18) 0.0345(4) Uani 1 1 d . U . . .
O2 O 0.7230(2) 0.77526(18) 0.81940(19) 0.0362(4) Uani 1 1 d . U . . .
O3 O 0.18232(17) 0.71169(16) 0.60361(17) 0.0259(3) Uani 1 1 d . U . . .
O4 O 0.29051(19) 0.85789(17) 0.70022(18) 0.0306(3) Uani 1 1 d . U . . .
C1 C 0.2504(3) 0.7650(2) 0.4105(2) 0.0248(3) Uani 1 1 d . U . . .
C2 C 0.1394(3) 0.8018(2) 0.3185(2) 0.0279(4) Uani 1 1 d . U . . .
H2A H 0.036760 0.772333 0.309368 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1826(3) 0.8834(2) 0.2396(3) 0.0307(4) Uani 1 1 d . U . . .
H3A H 0.108643 0.910607 0.176225 0.037 Uiso 1 1 calc R U . . .
C4 C 0.3327(3) 0.9254(2) 0.2529(3) 0.0308(4) Uani 1 1 d . U . . .
H4A H 0.360159 0.982478 0.199570 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4436(3) 0.8857(2) 0.3426(2) 0.0283(4) Uani 1 1 d . U . . .
H5A H 0.545919 0.913190 0.350890 0.034 Uiso 1 1 calc R U . . .
C6 C 0.3979(3) 0.8044(2) 0.4189(2) 0.0249(3) Uani 1 1 d . U . . .
C7 C 0.2381(3) 0.6716(2) 0.5012(2) 0.0239(3) Uani 1 1 d . U . . .
C8 C 0.1244(3) 0.5212(2) 0.4041(2) 0.0269(4) Uani 1 1 d . U . . .
H8A H 0.155785 0.485981 0.329784 0.040 Uiso 1 1 calc R U . . .
H8B H 0.124449 0.459570 0.463145 0.040 Uiso 1 1 calc R U . . .
H8C H 0.020195 0.521743 0.357235 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2071(3) 0.9187(3) 0.7654(3) 0.0328(4) Uani 1 1 d . U . . .
C10 C 0.0754(4) 0.9329(4) 0.6464(4) 0.0543(7) Uani 1 1 d . U . . .
H10A H 0.017015 0.974138 0.688496 0.082 Uiso 1 1 calc R U . . .
H10B H 0.117558 0.994307 0.599791 0.082 Uiso 1 1 calc R U . . .
H10C H 0.006506 0.839248 0.574053 0.082 Uiso 1 1 calc R U . . .
C11 C 0.3274(3) 1.0638(3) 0.8676(3) 0.0408(5) Uani 1 1 d . U . . .
H11A H 0.281331 1.114583 0.918009 0.061 Uiso 1 1 calc R U . . .
H11B H 0.415488 1.052916 0.938803 0.061 Uiso 1 1 calc R U . . .
H11C H 0.362781 1.117507 0.811737 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1528(4) 0.8339(3) 0.8486(3) 0.0519(6) Uani 1 1 d . U . . .
H12A H 0.096719 0.877969 0.891486 0.078 Uiso 1 1 calc R U . . .
H12B H 0.084017 0.737520 0.783025 0.078 Uiso 1 1 calc R U . . .
H12C H 0.242302 0.830803 0.925868 0.078 Uiso 1 1 calc R U . . .
C13 C 0.4062(3) 0.6801(2) 0.5752(2) 0.0240(3) Uani 1 1 d . U . . .
C14 C 0.4574(3) 0.6222(2) 0.6812(2) 0.0264(3) Uani 1 1 d . U . . .
C15 C 0.3459(3) 0.5240(2) 0.7069(3) 0.0279(4) Uani 1 1 d . U . . .
C16 C 0.6208(3) 0.6628(2) 0.7835(3) 0.0290(4) Uani 1 1 d . U . . .
C17 C 0.7908(3) 0.5936(3) 0.9564(3) 0.0369(5) Uani 1 1 d . U . . .
H17A H 0.801583 0.659326 1.045579 0.044 Uiso 1 1 calc R U . . .
H17B H 0.875436 0.639241 0.933221 0.044 Uiso 1 1 calc R U . . .
C18 C 0.7976(3) 0.4574(3) 0.9776(3) 0.0395(6) Uani 1 1 d . U . . .
H18A H 0.897129 0.476011 1.057791 0.059 Uiso 1 1 calc R U . . .
H18B H 0.713286 0.413435 1.000375 0.059 Uiso 1 1 calc R U . . .
H18C H 0.786793 0.393445 0.888543 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6357(3) 0.7487(3) 0.5227(3) 0.0306(5) Uani 1 1 d . U . . .
H19A H 0.668787 0.808034 0.470005 0.046 Uiso 1 1 calc R U . . .
H19B H 0.713212 0.785979 0.624294 0.046 Uiso 1 1 calc R U . . .
H19C H 0.624880 0.651667 0.478508 0.046 Uiso 1 1 calc R U . . .
N1 N 0.2596(3) 0.4421(2) 0.7253(2) 0.0373(5) Uani 1 1 d . U . . .
N2 N 0.4874(2) 0.74940(19) 0.5156(2) 0.0246(3) Uani 1 1 d . 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 C16 1.344(3) . ?
O1 C17 1.456(3) . ?
O2 C16 1.208(3) . ?
O3 C7 1.418(3) . ?
O3 O4 1.487(2) . ?
O4 C9 1.441(3) . ?
C1 C6 1.383(3) . ?
C1 C2 1.385(3) . ?
C1 C7 1.506(3) . ?
C2 C3 1.396(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.391(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.393(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5A 0.9500 . ?
C6 N2 1.420(3) . ?
C7 C8 1.530(3) . ?
C7 C13 1.543(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C12 1.497(4) . ?
C9 C10 1.519(4) . ?
C9 C11 1.520(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N2 1.345(3) . ?
C13 C14 1.376(3) . ?
C14 C15 1.442(3) . ?
C14 C16 1.475(3) . ?
C15 N1 1.143(3) . ?
C17 C18 1.497(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 N2 1.458(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C16 O1 C17 116.44(19) . . ?
C7 O3 O4 106.22(14) . . ?
C9 O4 O3 106.39(15) . . ?
C6 C1 C2 120.3(2) . . ?
C6 C1 C7 108.66(19) . . ?
C2 C1 C7 130.7(2) . . ?
C1 C2 C3 118.0(2) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 H4A 119.3 . . ?
C5 C4 H4A 119.3 . . ?
C6 C5 C4 116.8(2) . . ?
C6 C5 H5A 121.6 . . ?
C4 C5 H5A 121.6 . . ?
C5 C6 C1 122.7(2) . . ?
C5 C6 N2 127.8(2) . . ?
C1 C6 N2 109.46(19) . . ?
O3 C7 C1 115.74(18) . . ?
O3 C7 C8 104.73(17) . . ?
C1 C7 C8 110.21(18) . . ?
O3 C7 C13 111.94(17) . . ?
C1 C7 C13 101.96(17) . . ?
C8 C7 C13 112.52(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 C12 111.5(2) . . ?
O4 C9 C10 108.1(2) . . ?
C12 C9 C10 112.8(3) . . ?
O4 C9 C11 103.07(19) . . ?
C12 C9 C11 110.4(2) . . ?
C10 C9 C11 110.5(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C14 127.9(2) . . ?
N2 C13 C7 108.07(18) . . ?
C14 C13 C7 124.0(2) . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 C16 124.9(2) . . ?
C15 C14 C16 115.4(2) . . ?
N1 C15 C14 177.3(3) . . ?
O2 C16 O1 123.8(2) . . ?
O2 C16 C14 125.4(2) . . ?
O1 C16 C14 110.8(2) . . ?
O1 C17 C18 106.8(2) . . ?
O1 C17 H17A 110.4 . . ?
C18 C17 H17A 110.4 . . ?
O1 C17 H17B 110.4 . . ?
C18 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
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 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 N2 C6 111.23(18) . . ?
C13 N2 C19 126.5(2) . . ?
C6 N2 C19 121.31(19) . . ?

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
C7 O3 O4 C9 158.41(17) . . . . ?
C6 C1 C2 C3 -2.3(3) . . . . ?
C7 C1 C2 C3 -175.5(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C1 -1.1(3) . . . . ?
C4 C5 C6 N2 179.3(2) . . . . ?
C2 C1 C6 C5 2.7(3) . . . . ?
C7 C1 C6 C5 177.3(2) . . . . ?
C2 C1 C6 N2 -177.64(19) . . . . ?
C7 C1 C6 N2 -3.1(2) . . . . ?
O4 O3 C7 C1 -58.5(2) . . . . ?
O4 O3 C7 C8 179.95(15) . . . . ?
O4 O3 C7 C13 57.8(2) . . . . ?
C6 C1 C7 O3 128.3(2) . . . . ?
C2 C1 C7 O3 -57.9(3) . . . . ?
C6 C1 C7 C8 -113.2(2) . . . . ?
C2 C1 C7 C8 60.6(3) . . . . ?
C6 C1 C7 C13 6.5(2) . . . . ?
C2 C1 C7 C13 -179.7(2) . . . . ?
O3 O4 C9 C12 58.7(3) . . . . ?
O3 O4 C9 C10 -65.9(2) . . . . ?
O3 O4 C9 C11 177.13(18) . . . . ?
O3 C7 C13 N2 -132.27(19) . . . . ?
C1 C7 C13 N2 -7.9(2) . . . . ?
C8 C7 C13 N2 110.1(2) . . . . ?
O3 C7 C13 C14 49.1(3) . . . . ?
C1 C7 C13 C14 173.4(2) . . . . ?
C8 C7 C13 C14 -68.5(3) . . . . ?
N2 C13 C14 C15 -165.4(2) . . . . ?
C7 C13 C14 C15 12.9(3) . . . . ?
N2 C13 C14 C16 20.9(4) . . . . ?
C7 C13 C14 C16 -160.7(2) . . . . ?
C17 O1 C16 O2 7.8(4) . . . . ?
C17 O1 C16 C14 -170.1(2) . . . . ?
C13 C14 C16 O2 24.2(4) . . . . ?
C15 C14 C16 O2 -149.7(2) . . . . ?
C13 C14 C16 O1 -157.9(2) . . . . ?
C15 C14 C16 O1 28.2(3) . . . . ?
C16 O1 C17 C18 -169.4(2) . . . . ?
C14 C13 N2 C6 -174.8(2) . . . . ?
C7 C13 N2 C6 6.7(2) . . . . ?
C14 C13 N2 C19 16.5(4) . . . . ?
C7 C13 N2 C19 -162.1(2) . . . . ?
C5 C6 N2 C13 177.2(2) . . . . ?
C1 C6 N2 C13 -2.4(3) . . . . ?
C5 C6 N2 C19 -13.4(3) . . . . ?
C1 C6 N2 C19 167.0(2) . . . . ?

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_Compound3s
_database_code_depnum_ccdc_archive 'CCDC 2064846'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-06-01 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         'C17 H20 N2 O4'
_chemical_formula_sum            'C17 H20 N2 O4'
_chemical_formula_weight         316.35

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.7888(4)
_cell_length_b                   19.6193(8)
_cell_length_c                   10.0883(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.798(5)
_cell_angle_gamma                90
_cell_volume                     1636.71(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2757
_cell_measurement_theta_min      5.1520
_cell_measurement_theta_max      73.0580

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.758
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            7853
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.507
_diffrn_reflns_theta_max         69.999
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3082
_reflns_number_gt                2501
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0705P)²+0.3799P] 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_number_reflns         3082
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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 0.91294(13) 0.17392(5) 0.38639(11) 0.0238(3) Uani 1 1 d . . . . .
O2 O 1.02012(14) 0.12436(6) 0.35021(11) 0.0257(3) Uani 1 1 d . . . . .
O3 O 0.61780(16) -0.05177(6) 0.41422(13) 0.0347(3) Uani 1 1 d . . . . .
O4 O 0.45768(15) -0.01195(6) 0.20300(12) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.86436(16) 0.03096(7) 0.56531(14) 0.0247(3) Uani 1 1 d . . . . .
H1A H 0.832844 -0.011269 0.570002 0.030 Uiso 1 1 calc R U . . .
N2 N 0.55937(19) 0.14758(8) 0.14142(16) 0.0363(4) Uani 1 1 d . . . . .
C1 C 0.9997(2) 0.06154(9) 0.66782(16) 0.0242(3) Uani 1 1 d . . . . .
C2 C 1.1077(2) 0.03310(9) 0.78916(17) 0.0280(4) Uani 1 1 d . . . . .
H2A H 1.098122 -0.012927 0.814510 0.034 Uiso 1 1 calc R U . . .
C3 C 1.2308(2) 0.07509(9) 0.87201(17) 0.0304(4) Uani 1 1 d . . . . .
H3A H 1.306944 0.057329 0.955948 0.036 Uiso 1 1 calc R U . . .
C4 C 1.2450(2) 0.14256(10) 0.83487(18) 0.0315(4) Uani 1 1 d . . . . .
H4A H 1.330818 0.169947 0.893167 0.038 Uiso 1 1 calc R U . . .
C5 C 1.1344(2) 0.17026(9) 0.71272(17) 0.0279(4) Uani 1 1 d . . . . .
H5A H 1.142750 0.216358 0.687173 0.034 Uiso 1 1 calc R U . . .
C6 C 1.0123(2) 0.12861(8) 0.63011(16) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.8720(2) 0.14452(8) 0.49771(16) 0.0228(3) Uani 1 1 d . . . . .
C8 C 0.7556(2) 0.19607(9) 0.52499(18) 0.0295(4) Uani 1 1 d . . . . .
H8A H 0.720456 0.179617 0.601721 0.044 Uiso 1 1 calc R U . . .
H8B H 0.810427 0.240040 0.551345 0.044 Uiso 1 1 calc R U . . .
H8C H 0.661164 0.201612 0.439406 0.044 Uiso 1 1 calc R U . . .
C9 C 1.1049(2) 0.16285(9) 0.27382(16) 0.0263(4) Uani 1 1 d . . . . .
C10 C 1.2154(2) 0.21479(11) 0.3713(2) 0.0408(5) Uani 1 1 d . . . . .
H10A H 1.272419 0.240692 0.319520 0.061 Uiso 1 1 calc R U . . .
H10B H 1.150837 0.246003 0.406629 0.061 Uiso 1 1 calc R U . . .
H10C H 1.294194 0.191216 0.450795 0.061 Uiso 1 1 calc R U . . .
C11 C 1.2031(3) 0.10836(11) 0.2336(2) 0.0397(5) Uani 1 1 d . . . . .
H11A H 1.266248 0.129079 0.180564 0.060 Uiso 1 1 calc R U . . .
H11B H 1.276466 0.086852 0.319042 0.060 Uiso 1 1 calc R U . . .
H11C H 1.130225 0.073866 0.175109 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9830(2) 0.19529(11) 0.14438(19) 0.0396(5) Uani 1 1 d . . . . .
H12A H 1.040359 0.221252 0.092925 0.059 Uiso 1 1 calc R U . . .
H12B H 0.917843 0.159585 0.083167 0.059 Uiso 1 1 calc R U . . .
H12C H 0.912174 0.225956 0.173592 0.059 Uiso 1 1 calc R U . . .
C13 C 0.79009(19) 0.07428(8) 0.46022(16) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.65997(19) 0.05968(8) 0.34236(16) 0.0243(3) Uani 1 1 d . . . . .
C15 C 0.6045(2) 0.10877(9) 0.23175(17) 0.0268(4) Uani 1 1 d . . . . .
C16 C 0.5802(2) -0.00648(9) 0.32641(17) 0.0262(4) Uani 1 1 d . . . . .
C17 C 0.3690(2) -0.07520(10) 0.1786(2) 0.0395(5) Uani 1 1 d . . . . .
H17A H 0.283252 -0.073663 0.086302 0.059 Uiso 1 1 calc R U . . .
H17B H 0.442660 -0.113011 0.180617 0.059 Uiso 1 1 calc R U . . .
H17C H 0.320926 -0.081928 0.252184 0.059 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 C7 1.4131(19) . ?
O1 O2 1.4829(15) . ?
O2 C9 1.4519(19) . ?
O3 C16 1.219(2) . ?
O4 C16 1.346(2) . ?
O4 C17 1.441(2) . ?
N1 C13 1.343(2) . ?
N1 C1 1.418(2) . ?
N1 H1A 0.8800 . ?
N2 C15 1.150(2) . ?
C1 C6 1.384(2) . ?
C1 C2 1.387(2) . ?
C2 C3 1.391(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.396(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.512(2) . ?
C7 C8 1.529(2) . ?
C7 C13 1.541(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.513(3) . ?
C9 C10 1.517(2) . ?
C9 C12 1.520(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.372(2) . ?
C14 C15 1.429(2) . ?
C14 C16 1.458(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C7 O1 O2 106.37(10) . . ?
C9 O2 O1 105.81(11) . . ?
C16 O4 C17 116.32(14) . . ?
C13 N1 C1 111.80(13) . . ?
C13 N1 H1A 124.1 . . ?
C1 N1 H1A 124.1 . . ?
C6 C1 C2 122.04(15) . . ?
C6 C1 N1 109.07(13) . . ?
C2 C1 N1 128.88(16) . . ?
C1 C2 C3 116.90(16) . . ?
C1 C2 H2A 121.6 . . ?
C3 C2 H2A 121.6 . . ?
C2 C3 C4 121.59(16) . . ?
C2 C3 H3A 119.2 . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 C5 120.55(16) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 117.96(16) . . ?
C6 C5 H5A 121.0 . . ?
C4 C5 H5A 121.0 . . ?
C5 C6 C1 120.96(15) . . ?
C5 C6 C7 130.18(15) . . ?
C1 C6 C7 108.79(14) . . ?
O1 C7 C6 115.82(13) . . ?
O1 C7 C8 103.83(12) . . ?
C6 C7 C8 111.89(13) . . ?
O1 C7 C13 113.17(12) . . ?
C6 C7 C13 101.86(13) . . ?
C8 C7 C13 110.49(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C11 102.52(14) . . ?
O2 C9 C10 109.63(13) . . ?
C11 C9 C10 110.51(15) . . ?
O2 C9 C12 109.56(13) . . ?
C11 C9 C12 111.44(15) . . ?
C10 C9 C12 112.69(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 126.27(15) . . ?
N1 C13 C7 108.07(13) . . ?
C14 C13 C7 125.61(14) . . ?
C13 C14 C15 119.99(15) . . ?
C13 C14 C16 120.66(15) . . ?
C15 C14 C16 119.32(14) . . ?
N2 C15 C14 179.08(18) . . ?
O3 C16 O4 123.30(16) . . ?
O3 C16 C14 124.54(15) . . ?
O4 C16 C14 112.15(14) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C7 O1 O2 C9 -160.80(12) . . . . ?
C13 N1 C1 C6 1.66(19) . . . . ?
C13 N1 C1 C2 -178.64(16) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
N1 C1 C2 C3 -179.89(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C4 C5 C6 C7 176.75(16) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C5 179.81(15) . . . . ?
C2 C1 C6 C7 -177.03(15) . . . . ?
N1 C1 C6 C7 2.69(18) . . . . ?
O2 O1 C7 C6 59.65(15) . . . . ?
O2 O1 C7 C8 -177.29(11) . . . . ?
O2 O1 C7 C13 -57.45(15) . . . . ?
C5 C6 C7 O1 54.7(2) . . . . ?
C1 C6 C7 O1 -128.59(15) . . . . ?
C5 C6 C7 C8 -64.1(2) . . . . ?
C1 C6 C7 C8 112.69(16) . . . . ?
C5 C6 C7 C13 177.90(17) . . . . ?
C1 C6 C7 C13 -5.33(16) . . . . ?
O1 O2 C9 C11 -176.77(12) . . . . ?
O1 O2 C9 C10 65.82(16) . . . . ?
O1 O2 C9 C12 -58.33(16) . . . . ?
C1 N1 C13 C14 177.15(15) . . . . ?
C1 N1 C13 C7 -5.16(17) . . . . ?
O1 C7 C13 N1 131.33(14) . . . . ?
C6 C7 C13 N1 6.30(16) . . . . ?
C8 C7 C13 N1 -112.72(15) . . . . ?
O1 C7 C13 C14 -51.0(2) . . . . ?
C6 C7 C13 C14 -175.99(15) . . . . ?
C8 C7 C13 C14 64.99(19) . . . . ?
N1 C13 C14 C15 -173.17(15) . . . . ?
C7 C13 C14 C15 9.5(2) . . . . ?
N1 C13 C14 C16 4.9(3) . . . . ?
C7 C13 C14 C16 -172.42(15) . . . . ?
C17 O4 C16 O3 0.6(2) . . . . ?
C17 O4 C16 C14 -178.82(15) . . . . ?
C13 C14 C16 O3 2.0(3) . . . . ?
C15 C14 C16 O3 -179.90(16) . . . . ?
C13 C14 C16 O4 -178.61(14) . . . . ?
C15 C14 C16 O4 -0.5(2) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_Compound3a
_database_code_depnum_ccdc_archive 'CCDC 2064845'
loop_
_audit_author_name
_audit_author_address
'Deguang Huang'
;Fujian Institute of Research on the Structure of Matter, CAS
China
;
_audit_update_record             
;
2021-02-24 deposited with the CCDC.	2021-06-01 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         'C18 H22 N2 O4'
_chemical_formula_sum            'C18 H22 N2 O4'
_chemical_formula_weight         330.37

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.0953(3)
_cell_length_b                   19.6563(5)
_cell_length_c                   10.0974(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.550(4)
_cell_angle_gamma                90
_cell_volume                     1701.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3352
_cell_measurement_theta_min      4.4800
_cell_measurement_theta_max      72.5420

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.751
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            7832
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.499
_diffrn_reflns_theta_max         69.967
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3204
_reflns_number_gt                2607
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0547P)²+0.4288P] 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_number_reflns         3204
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1059
_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
O1 O 0.57164(13) 0.67760(5) 0.60494(11) 0.0203(2) Uani 1 1 d . . . . .
O2 O 0.48373(13) 0.62639(5) 0.65572(11) 0.0214(3) Uani 1 1 d . . . . .
O3 O 0.84662(14) 0.45550(6) 0.54005(12) 0.0275(3) Uani 1 1 d . . . . .
O4 O 1.02081(13) 0.49037(6) 0.74504(11) 0.0229(3) Uani 1 1 d . . . . .
N1 N 0.60357(15) 0.53566(7) 0.41717(13) 0.0201(3) Uani 1 1 d . . . . .
H1A H 0.633202 0.493545 0.410561 0.024 Uiso 1 1 calc R U . . .
N2 N 0.93985(19) 0.64941(8) 0.82805(17) 0.0350(4) Uani 1 1 d . . . . .
C1 C 0.46782(18) 0.56535(8) 0.32229(16) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.35983(19) 0.53610(9) 0.20543(17) 0.0234(3) Uani 1 1 d . . . . .
H2A H 0.368986 0.490167 0.180004 0.028 Uiso 1 1 calc R U . . .
C3 C 0.2368(2) 0.57733(9) 0.12668(17) 0.0256(4) Uani 1 1 d . . . . .
H3A H 0.160265 0.559172 0.045435 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2239(2) 0.64428(9) 0.16464(17) 0.0262(4) Uani 1 1 d . . . . .
H4A H 0.138524 0.671141 0.109481 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3350(2) 0.67278(8) 0.28309(17) 0.0235(3) Uani 1 1 d . . . . .
H5A H 0.326984 0.718793 0.308627 0.028 Uiso 1 1 calc R U . . .
C6 C 0.45675(18) 0.63208(8) 0.36191(16) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.59914(18) 0.64871(8) 0.48711(16) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.7030(2) 0.70099(8) 0.44970(18) 0.0241(4) Uani 1 1 d . . . . .
H8A H 0.728462 0.685055 0.367975 0.036 Uiso 1 1 calc R U . . .
H8B H 0.647881 0.744567 0.427466 0.036 Uiso 1 1 calc R U . . .
H8C H 0.799440 0.706903 0.529655 0.036 Uiso 1 1 calc R U . . .
C9 C 0.39522(19) 0.66448(8) 0.72749(16) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.2662(2) 0.70456(9) 0.62047(18) 0.0298(4) Uani 1 1 d . . . . .
H10A H 0.206838 0.730118 0.668964 0.045 Uiso 1 1 calc R U . . .
H10B H 0.312297 0.736260 0.570511 0.045 Uiso 1 1 calc R U . . .
H10C H 0.196312 0.673092 0.553027 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5051(2) 0.70996(9) 0.83847(18) 0.0273(4) Uani 1 1 d . . . . .
H11A H 0.445665 0.735588 0.886768 0.041 Uiso 1 1 calc R U . . .
H11B H 0.583756 0.681930 0.906741 0.041 Uiso 1 1 calc R U . . .
H11C H 0.556889 0.741739 0.793556 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3295(2) 0.60838(9) 0.79430(19) 0.0290(4) Uani 1 1 d . . . . .
H12A H 0.266677 0.628458 0.846380 0.044 Uiso 1 1 calc R U . . .
H12B H 0.263992 0.578243 0.720837 0.044 Uiso 1 1 calc R U . . .
H12C H 0.415449 0.582155 0.858863 0.044 Uiso 1 1 calc R U . . .
C13 C 0.68235(18) 0.57919(8) 0.51883(15) 0.0184(3) Uani 1 1 d . . . . .
C14 C 0.81727(18) 0.56457(8) 0.62678(16) 0.0199(3) Uani 1 1 d . . . . .
C15 C 0.88423(19) 0.61250(8) 0.73725(17) 0.0240(4) Uani 1 1 d . . . . .
C16 C 0.89316(18) 0.49857(8) 0.63127(16) 0.0213(3) Uani 1 1 d . . . . .
C17 C 1.1025(2) 0.42668(9) 0.74780(18) 0.0256(4) Uani 1 1 d . . . . .
H17A H 1.143404 0.424850 0.668499 0.031 Uiso 1 1 calc R U . . .
H17B H 1.030565 0.387848 0.739125 0.031 Uiso 1 1 calc R U . . .
C18 C 1.2345(2) 0.42293(10) 0.8851(2) 0.0359(4) Uani 1 1 d . . . . .
H18A H 1.291711 0.380270 0.889642 0.054 Uiso 1 1 calc R U . . .
H18B H 1.305120 0.461474 0.892431 0.054 Uiso 1 1 calc R U . . .
H18C H 1.192711 0.424612 0.962788 0.054 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 C7 1.4141(18) . ?
O1 O2 1.4799(15) . ?
O2 C9 1.4574(18) . ?
O3 C16 1.218(2) . ?
O4 C16 1.3420(19) . ?
O4 C17 1.4514(19) . ?
N1 C13 1.344(2) . ?
N1 C1 1.411(2) . ?
N1 H1A 0.8800 . ?
N2 C15 1.146(2) . ?
C1 C2 1.383(2) . ?
C1 C6 1.385(2) . ?
C2 C3 1.395(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.399(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.512(2) . ?
C7 C8 1.527(2) . ?
C7 C13 1.543(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C12 1.516(2) . ?
C9 C11 1.518(2) . ?
C9 C10 1.522(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.372(2) . ?
C14 C15 1.431(2) . ?
C14 C16 1.463(2) . ?
C17 C18 1.501(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
C7 O1 O2 106.65(10) . . ?
C9 O2 O1 105.98(10) . . ?
C16 O4 C17 114.24(12) . . ?
C13 N1 C1 112.14(13) . . ?
C13 N1 H1A 123.9 . . ?
C1 N1 H1A 123.9 . . ?
C2 C1 C6 122.73(15) . . ?
C2 C1 N1 128.15(15) . . ?
C6 C1 N1 109.10(13) . . ?
C1 C2 C3 116.76(15) . . ?
C1 C2 H2A 121.6 . . ?
C3 C2 H2A 121.6 . . ?
C4 C3 C2 121.31(15) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 120.85(15) . . ?
C3 C4 H4A 119.6 . . ?
C5 C4 H4A 119.6 . . ?
C6 C5 C4 118.10(15) . . ?
C6 C5 H5A 121.0 . . ?
C4 C5 H5A 121.0 . . ?
C5 C6 C1 120.24(15) . . ?
C5 C6 C7 130.79(15) . . ?
C1 C6 C7 108.76(14) . . ?
O1 C7 C6 116.56(13) . . ?
O1 C7 C8 103.66(12) . . ?
C6 C7 C8 111.50(13) . . ?
O1 C7 C13 113.18(12) . . ?
C6 C7 C13 101.85(12) . . ?
C8 C7 C13 110.26(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C12 102.31(13) . . ?
O2 C9 C11 109.44(13) . . ?
C12 C9 C11 111.11(14) . . ?
O2 C9 C10 109.62(12) . . ?
C12 C9 C10 111.55(14) . . ?
C11 C9 C10 112.34(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 125.46(15) . . ?
N1 C13 C7 107.83(13) . . ?
C14 C13 C7 126.63(14) . . ?
C13 C14 C15 121.05(15) . . ?
C13 C14 C16 119.84(14) . . ?
C15 C14 C16 119.09(14) . . ?
N2 C15 C14 178.11(18) . . ?
O3 C16 O4 123.11(15) . . ?
O3 C16 C14 123.50(15) . . ?
O4 C16 C14 113.39(13) . . ?
O4 C17 C18 107.82(14) . . ?
O4 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O4 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.5 . . ?
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 . . ?

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
C7 O1 O2 C9 -154.08(11) . . . . ?
C13 N1 C1 C2 179.65(15) . . . . ?
C13 N1 C1 C6 0.68(18) . . . . ?
C6 C1 C2 C3 0.3(2) . . . . ?
N1 C1 C2 C3 -178.56(15) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C4 C5 C6 C7 175.01(16) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
N1 C1 C6 C5 178.43(14) . . . . ?
C2 C1 C6 C7 -175.97(14) . . . . ?
N1 C1 C6 C7 3.06(17) . . . . ?
O2 O1 C7 C6 62.45(15) . . . . ?
O2 O1 C7 C8 -174.65(11) . . . . ?
O2 O1 C7 C13 -55.19(15) . . . . ?
C5 C6 C7 O1 56.5(2) . . . . ?
C1 C6 C7 O1 -128.75(14) . . . . ?
C5 C6 C7 C8 -62.2(2) . . . . ?
C1 C6 C7 C8 112.52(15) . . . . ?
C5 C6 C7 C13 -179.78(16) . . . . ?
C1 C6 C7 C13 -5.06(16) . . . . ?
O1 O2 C9 C12 -171.72(11) . . . . ?
O1 O2 C9 C11 -53.83(15) . . . . ?
O1 O2 C9 C10 69.79(15) . . . . ?
C1 N1 C13 C14 179.09(14) . . . . ?
C1 N1 C13 C7 -4.02(17) . . . . ?
O1 C7 C13 N1 131.37(13) . . . . ?
C6 C7 C13 N1 5.44(15) . . . . ?
C8 C7 C13 N1 -113.03(14) . . . . ?
O1 C7 C13 C14 -51.8(2) . . . . ?
C6 C7 C13 C14 -177.73(15) . . . . ?
C8 C7 C13 C14 63.81(19) . . . . ?
N1 C13 C14 C15 -174.05(15) . . . . ?
C7 C13 C14 C15 9.6(2) . . . . ?
N1 C13 C14 C16 4.8(2) . . . . ?
C7 C13 C14 C16 -171.50(14) . . . . ?
C17 O4 C16 O3 2.2(2) . . . . ?
C17 O4 C16 C14 -176.91(13) . . . . ?
C13 C14 C16 O3 3.1(2) . . . . ?
C15 C14 C16 O3 -178.03(15) . . . . ?
C13 C14 C16 O4 -177.81(14) . . . . ?
C15 C14 C16 O4 1.1(2) . . . . ?
C16 O4 C17 C18 -175.99(14) . . . . ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.047



