# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2128471'
loop_
_audit_author_name
_audit_author_address
'Daniel Strand' 'Lund University'
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-02-15 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         'C23 H24 N2 O6'
_chemical_formula_sum            'C23 H24 N2 O6'
_chemical_formula_weight         424.44

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.6019(6)
_cell_length_b                   16.1146(7)
_cell_length_c                   9.4624(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.538(4)
_cell_angle_gamma                90
_cell_volume                     2073.31(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3093
_cell_measurement_theta_min      3.6090
_cell_measurement_theta_max      26.8680

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_T_min  0.95066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1367
_diffrn_reflns_number            16114
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.939
_diffrn_reflns_theta_max         29.348
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4942
_reflns_number_gt                3277
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0415P)²+0.4250P] 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         4942
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1029
_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 0.76325(14) 0.15307(11) 0.00723(17) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.68377(13) 0.09646(10) -0.05474(17) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.703093 0.072969 -0.145397 0.027 Uiso 1 1 calc R U . . .
C3 C 0.56957(14) 0.04740(11) 0.10875(18) 0.0249(4) Uani 1 1 d . . . . .
C4 C 0.53161(13) 0.13013(11) 0.05691(18) 0.0254(4) Uani 1 1 d . . . . .
H4A H 0.540329 0.172139 0.129591 0.031 Uiso 1 1 calc R U . . .
H4B H 0.462283 0.126538 0.030838 0.031 Uiso 1 1 calc R U . . .
C5 C 0.59237(13) 0.15122(11) -0.07215(17) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.555917 0.137843 -0.159951 0.027 Uiso 1 1 calc R U . . .
C6 C 0.63531(13) 0.23981(11) -0.07812(18) 0.0216(4) Uani 1 1 d . . . . .
H6 H 0.646859 0.255170 -0.176502 0.026 Uiso 1 1 calc R U . . .
C7 C 0.56791(14) 0.30283(11) -0.01175(18) 0.0245(4) Uani 1 1 d . . . . .
C8A C 0.4203(15) 0.3727(11) -0.0348(16) 0.042(3) Uani 0.550(16) 1 d . . P A 1
H8A1 H 0.445897 0.425904 -0.002965 0.051 Uiso 0.550(16) 1 calc R U P A 1
H8A2 H 0.395225 0.343087 0.045831 0.051 Uiso 0.550(16) 1 calc R U P A 1
C9A C 0.3387(5) 0.3848(6) -0.1489(8) 0.0438(17) Uani 0.550(16) 1 d . . P A 1
H9A1 H 0.364976 0.413592 -0.228325 0.066 Uiso 0.550(16) 1 calc R U P A 1
H9A2 H 0.286135 0.416786 -0.110604 0.066 Uiso 0.550(16) 1 calc R U P A 1
H9A3 H 0.314098 0.331664 -0.178945 0.066 Uiso 0.550(16) 1 calc R U P A 1
C8B C 0.4230(18) 0.3900(13) -0.0666(19) 0.040(3) Uani 0.450(16) 1 d . . P A 2
H8B1 H 0.429891 0.406242 0.031908 0.049 Uiso 0.450(16) 1 calc R U P A 2
H8B2 H 0.430581 0.438764 -0.125479 0.049 Uiso 0.450(16) 1 calc R U P A 2
C9B C 0.3314(6) 0.3515(8) -0.0941(16) 0.064(3) Uani 0.450(16) 1 d . . P A 2
H9B1 H 0.326402 0.335736 -0.191826 0.096 Uiso 0.450(16) 1 calc R U P A 2
H9B2 H 0.279399 0.389479 -0.073184 0.096 Uiso 0.450(16) 1 calc R U P A 2
H9B3 H 0.326023 0.302988 -0.035837 0.096 Uiso 0.450(16) 1 calc R U P A 2
C10 C 0.78624(13) 0.30425(11) 0.04130(18) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.84340(14) 0.30253(11) 0.16462(18) 0.0252(4) Uani 1 1 d . . . . .
H11 H 0.845783 0.254593 0.219336 0.030 Uiso 1 1 calc R U . . .
C12 C 0.89710(13) 0.37169(11) 0.20714(18) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.936058 0.369762 0.289361 0.031 Uiso 1 1 calc R U . . .
C13 C 0.89273(14) 0.44382(11) 0.12702(19) 0.0269(4) Uani 1 1 d . . . . .
C14 C 0.83583(14) 0.44557(11) 0.00256(19) 0.0290(4) Uani 1 1 d . . . . .
H14 H 0.833167 0.493586 -0.051932 0.035 Uiso 1 1 calc R U . . .
C15 C 0.78330(14) 0.37620(11) -0.04026(19) 0.0282(4) Uani 1 1 d . . . . .
H15 H 0.745832 0.377547 -0.123899 0.034 Uiso 1 1 calc R U . . .
C16 C 1.00547(16) 0.51388(13) 0.2838(2) 0.0402(5) Uani 1 1 d . . . . .
H16A H 0.968712 0.500077 0.365750 0.060 Uiso 1 1 calc R U . . .
H16B H 1.035543 0.567324 0.296844 0.060 Uiso 1 1 calc R U . . .
H16C H 1.055547 0.472852 0.270466 0.060 Uiso 1 1 calc R U . . .
C17 C 0.71727(13) -0.04052(10) 0.07079(18) 0.0230(4) Uani 1 1 d . . . . .
C18 C 0.71572(15) -0.08210(12) 0.1987(2) 0.0333(5) Uani 1 1 d . . . . .
H18 H 0.675764 -0.062856 0.269908 0.040 Uiso 1 1 calc R U . . .
C19 C 0.77292(15) -0.15188(13) 0.2218(2) 0.0370(5) Uani 1 1 d . . . . .
H19 H 0.770936 -0.179144 0.308273 0.044 Uiso 1 1 calc R U . . .
C20 C 0.83343(14) -0.18187(11) 0.1172(2) 0.0291(4) Uani 1 1 d . . . . .
C21 C 0.83617(15) -0.14061(11) -0.0100(2) 0.0321(5) Uani 1 1 d . . . . .
H21 H 0.876598 -0.159671 -0.080818 0.039 Uiso 1 1 calc R U . . .
C22 C 0.77852(15) -0.07052(12) -0.0326(2) 0.0318(5) Uani 1 1 d . . . . .
H22 H 0.780986 -0.043034 -0.118820 0.038 Uiso 1 1 calc R U . . .
C23 C 0.95471(16) -0.28003(13) 0.0486(2) 0.0423(5) Uani 1 1 d . . . . .
H23A H 0.918448 -0.295807 -0.035546 0.063 Uiso 1 1 calc R U . . .
H23B H 0.990196 -0.327155 0.085412 0.063 Uiso 1 1 calc R U . . .
H23C H 1.000229 -0.236664 0.026713 0.063 Uiso 1 1 calc R U . . .
N1 N 0.72923(11) 0.23333(9) 0.00011(15) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.65747(11) 0.03129(9) 0.04535(14) 0.0225(3) Uani 1 1 d . . . . .
O1 O 0.84283(9) 0.13097(8) 0.05632(13) 0.0307(3) Uani 1 1 d . . . . .
O2 O 0.52977(10) 0.00231(8) 0.19382(14) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.94074(10) 0.51595(8) 0.16198(14) 0.0363(4) Uani 1 1 d . . . . .
O4 O 0.88793(11) -0.25086(8) 0.15223(15) 0.0411(4) Uani 1 1 d . . . . .
O5 O 0.57521(11) 0.32693(9) 0.10742(13) 0.0440(4) Uani 1 1 d . . . . .
O6 O 0.49701(10) 0.32441(9) -0.10238(14) 0.0404(4) 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 1.220(2) . ?
C1 N1 1.375(2) . ?
C1 C2 1.520(2) . ?
C2 N2 1.465(2) . ?
C2 C5 1.530(2) . ?
C2 H2 0.9800 . ?
C3 O2 1.222(2) . ?
C3 N2 1.377(2) . ?
C3 C4 1.507(2) . ?
C4 C5 1.531(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.544(2) . ?
C5 H5 0.9800 . ?
C6 N1 1.463(2) . ?
C6 C7 1.516(2) . ?
C6 H6 0.9800 . ?
C7 O5 1.194(2) . ?
C7 O6 1.320(2) . ?
C8A O6 1.463(19) . ?
C8A C9A 1.540(18) . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C9A H9A1 0.9600 . ?
C9A H9A2 0.9600 . ?
C9A H9A3 0.9600 . ?
C8B C9B 1.41(3) . ?
C8B O6 1.50(2) . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C9B H9B1 0.9600 . ?
C9B H9B2 0.9600 . ?
C9B H9B3 0.9600 . ?
C10 C11 1.385(2) . ?
C10 C15 1.393(2) . ?
C10 N1 1.429(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 O3 1.369(2) . ?
C13 C14 1.392(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O3 1.432(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.384(2) . ?
C17 C22 1.389(2) . ?
C17 N2 1.431(2) . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(3) . ?
C19 H19 0.9300 . ?
C20 O4 1.372(2) . ?
C20 C21 1.377(3) . ?
C21 C22 1.388(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O4 1.433(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
O1 C1 N1 125.98(17) . . ?
O1 C1 C2 125.91(16) . . ?
N1 C1 C2 108.10(15) . . ?
N2 C2 C1 111.36(13) . . ?
N2 C2 C5 105.74(14) . . ?
C1 C2 C5 105.24(14) . . ?
N2 C2 H2 111.4 . . ?
C1 C2 H2 111.4 . . ?
C5 C2 H2 111.4 . . ?
O2 C3 N2 125.48(17) . . ?
O2 C3 C4 125.92(17) . . ?
N2 C3 C4 108.60(15) . . ?
C3 C4 C5 105.57(14) . . ?
C3 C4 H4A 110.6 . . ?
C5 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C5 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?
C2 C5 C4 103.92(13) . . ?
C2 C5 C6 103.31(14) . . ?
C4 C5 C6 116.56(14) . . ?
C2 C5 H5 110.8 . . ?
C4 C5 H5 110.8 . . ?
C6 C5 H5 110.8 . . ?
N1 C6 C7 111.59(14) . . ?
N1 C6 C5 103.97(13) . . ?
C7 C6 C5 111.76(14) . . ?
N1 C6 H6 109.8 . . ?
C7 C6 H6 109.8 . . ?
C5 C6 H6 109.8 . . ?
O5 C7 O6 124.65(17) . . ?
O5 C7 C6 124.98(17) . . ?
O6 C7 C6 110.30(14) . . ?
O6 C8A C9A 105.7(11) . . ?
O6 C8A H8A1 110.6 . . ?
C9A C8A H8A1 110.6 . . ?
O6 C8A H8A2 110.6 . . ?
C9A C8A H8A2 110.6 . . ?
H8A1 C8A H8A2 108.7 . . ?
C8A C9A H9A1 109.5 . . ?
C8A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C8A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C9B C8B O6 104.0(16) . . ?
C9B C8B H8B1 111.0 . . ?
O6 C8B H8B1 111.0 . . ?
C9B C8B H8B2 111.0 . . ?
O6 C8B H8B2 111.0 . . ?
H8B1 C8B H8B2 109.0 . . ?
C8B C9B H9B1 109.5 . . ?
C8B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C8B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
C11 C10 C15 119.38(16) . . ?
C11 C10 N1 120.12(15) . . ?
C15 C10 N1 120.48(15) . . ?
C10 C11 C12 120.52(16) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C13 120.01(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
O3 C13 C12 124.45(17) . . ?
O3 C13 C14 115.97(16) . . ?
C12 C13 C14 119.58(17) . . ?
C15 C14 C13 120.21(17) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.27(17) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.09(17) . . ?
C18 C17 N2 121.10(16) . . ?
C22 C17 N2 120.80(15) . . ?
C19 C18 C17 120.69(18) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 120.80(17) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
O4 C20 C21 125.14(17) . . ?
O4 C20 C19 115.83(17) . . ?
C21 C20 C19 119.01(18) . . ?
C20 C21 C22 119.92(18) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 121.49(17) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 C10 124.03(15) . . ?
C1 N1 C6 112.35(14) . . ?
C10 N1 C6 122.73(14) . . ?
C3 N2 C17 125.14(14) . . ?
C3 N2 C2 112.12(14) . . ?
C17 N2 C2 122.74(14) . . ?
C13 O3 C16 116.98(15) . . ?
C20 O4 C23 116.66(15) . . ?
C7 O6 C8A 111.9(6) . . ?
C7 O6 C8B 121.4(8) . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2128469'
loop_
_audit_author_name
_audit_author_address
'Daniel Strand' 'Lund University'
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DIFMN02_shelx               
;
PROBLEM: The minimum difference density is < -0.1*ZMAX*1.00
RESPONSE: The alert originates from residual untreated twinning and overlap of reflections.
;
_vrf_PLAT097_shelx               
;
PROBLEM: Large Reported Max.  (Positive) Residual Density
RESPONSE: The alert originates from residual untreated twinning and overlap of reflections.
;
_vrf_PLAT098_shelx               
;
PROBLEM: Large Reported Min.  (Negative) Residual Density
RESPONSE: The alert originates from residual untreated twinning and overlap of reflections.
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............
RESPONSE: The alert originates from residual untreated twinning and overlap of reflections.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(+)-(2aS,4aS,6aS)-hexahydro-1,3,5-triazacyclopenta[cd]pentalene-2,4,6(1H)-trione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H7 N3 O3),C2 H3 N'
_chemical_formula_sum            'C16 H17 N7 O6'
_chemical_formula_weight         403.36

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   10.2416(18)
_cell_length_b                   9.0837(12)
_cell_length_c                   10.5564(16)
_cell_angle_alpha                90
_cell_angle_beta                 117.25(2)
_cell_angle_gamma                90
_cell_volume                     873.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2566
_cell_measurement_theta_min      4.3910
_cell_measurement_theta_max      27.3630

_exptl_crystal_description       irregular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_T_min  0.95720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1367
_diffrn_reflns_number            10598
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.764
_diffrn_reflns_theta_max         29.783
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.860
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             10598
_reflns_number_gt                5845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_max     0.803
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 _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    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 4-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1088P)²+1.2277P] 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 855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         10598
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2944
_refine_ls_wR_factor_gt          0.2775
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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 0.4856(13) 0.6792(15) 0.6825(13) 0.037(3) Uani 1 1 d . . . . .
C2 C 0.6184(14) 0.5876(15) 0.7046(14) 0.040(3) Uani 1 1 d . . . . .
H2 H 0.593954 0.509571 0.633140 0.048 Uiso 1 1 calc R U . . .
C3 C 0.8471(14) 0.7020(16) 0.8361(13) 0.038(3) Uani 1 1 d . . . . .
C4 C 0.8277(14) 0.6027(15) 0.9433(13) 0.036(3) Uani 1 1 d . . . . .
H4 H 0.907874 0.531387 0.987101 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6752(14) 0.6904(15) 1.0394(12) 0.035(3) Uani 1 1 d . . . . .
C6 C 0.5763(14) 0.5886(15) 0.9150(13) 0.037(3) Uani 1 1 d . . . . .
H6 H 0.530155 0.511055 0.945320 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6771(16) 0.5262(14) 0.8574(14) 0.043(3) Uani 1 1 d . . . . .
H7 H 0.683381 0.418515 0.861593 0.052 Uiso 1 1 calc R U . . .
N1 N 0.4696(11) 0.6759(14) 0.7991(11) 0.041(3) Uani 1 1 d . . . . .
H1A H 0.400194 0.722605 0.806179 0.049 Uiso 1 1 calc R U . . .
N2 N 0.7344(11) 0.6847(12) 0.7096(11) 0.039(2) Uani 1 1 d . . . . .
H2A H 0.729239 0.727690 0.634896 0.046 Uiso 1 1 calc R U . . .
N3 N 0.8096(12) 0.6900(12) 1.0486(10) 0.038(2) Uani 1 1 d . . . . .
H3A H 0.881000 0.738733 1.113252 0.045 Uiso 1 1 calc R U . . .
O1 O 0.4106(11) 0.7479(12) 0.5712(10) 0.057(3) Uani 1 1 d . . . . .
O2 O 0.9519(11) 0.7852(13) 0.8698(10) 0.062(3) Uani 1 1 d . . . . .
O3 O 0.6336(11) 0.7578(12) 1.1145(10) 0.052(3) Uani 1 1 d . . . . .
C101 C -0.0623(12) 0.4405(14) 0.6464(12) 0.030(2) Uani 1 1 d . . . . .
C102 C 0.0623(13) 0.5386(13) 0.6529(13) 0.033(3) Uani 1 1 d . . . . .
H102 H 0.091809 0.613277 0.727974 0.039 Uiso 1 1 calc R U . . .
C103 C 0.2051(12) 0.4451(13) 0.5478(11) 0.029(2) Uani 1 1 d . . . . .
C104 C 0.0924(13) 0.5428(13) 0.4347(12) 0.032(3) Uani 1 1 d . . . . .
H104 H 0.138300 0.620276 0.404034 0.039 Uiso 1 1 calc R U . . .
C105 C -0.1484(13) 0.4532(13) 0.2990(11) 0.031(2) Uani 1 1 d . . . . .
C106 C -0.1548(13) 0.5466(13) 0.4168(12) 0.032(3) Uani 1 1 d . . . . .
H106 H -0.228441 0.625097 0.378510 0.039 Uiso 1 1 calc R U . . .
C107 C -0.0003(15) 0.6068(13) 0.5028(14) 0.034(3) Uani 1 1 d . . . . .
H107 H 0.001826 0.714600 0.505459 0.041 Uiso 1 1 calc R U . . .
N101 N -0.1780(10) 0.4513(12) 0.5169(10) 0.032(2) Uani 1 1 d . . . . .
H11A H -0.259330 0.405903 0.494330 0.039 Uiso 1 1 calc R U . . .
N102 N 0.1848(10) 0.4504(12) 0.6642(10) 0.032(2) Uani 1 1 d . . . . .
H12A H 0.241184 0.404190 0.741140 0.039 Uiso 1 1 calc R U . . .
N103 N -0.0130(11) 0.4565(11) 0.3146(10) 0.033(2) Uani 1 1 d . . . . .
H13A H 0.011685 0.410548 0.257561 0.040 Uiso 1 1 calc R U . . .
O101 O -0.0551(9) 0.3620(11) 0.7442(8) 0.043(2) Uani 1 1 d . . . . .
O102 O 0.2974(9) 0.3708(10) 0.5336(9) 0.042(2) Uani 1 1 d . . . . .
O103 O -0.2534(9) 0.3845(11) 0.2080(9) 0.044(2) Uani 1 1 d . . . . .
C201 C 0.396(4) 0.610(3) 0.269(2) 0.139(12) Uani 1 1 d . . . . .
H20A H 0.331538 0.588797 0.310403 0.208 Uiso 1 1 calc R U . . .
H20B H 0.422134 0.711856 0.281836 0.208 Uiso 1 1 calc R U . . .
H20C H 0.482888 0.550534 0.314955 0.208 Uiso 1 1 calc R U . . .
C202 C 0.324(3) 0.577(2) 0.123(3) 0.090(6) Uani 1 1 d . . . . .
N201 N 0.279(3) 0.549(3) 0.005(2) 0.133(9) 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 1.238(16) . ?
C1 N1 1.315(15) . ?
C1 C2 1.519(18) . ?
C2 N2 1.460(18) . ?
C2 C7 1.545(19) . ?
C2 H2 0.9800 . ?
C3 O2 1.225(16) . ?
C3 N2 1.315(16) . ?
C3 C4 1.529(17) . ?
C4 N3 1.445(16) . ?
C4 C7 1.55(2) . ?
C4 H4 0.9800 . ?
C5 O3 1.223(15) . ?
C5 N3 1.334(16) . ?
C5 C6 1.545(17) . ?
C6 N1 1.447(17) . ?
C6 C7 1.527(18) . ?
C6 H6 0.9800 . ?
C7 H7 0.9800 . ?
N1 H1A 0.8600 . ?
N2 H2A 0.8600 . ?
N3 H3A 0.8600 . ?
C101 O101 1.229(14) . ?
C101 N101 1.341(15) . ?
C101 C102 1.532(17) . ?
C102 N102 1.447(15) . ?
C102 C107 1.541(17) . ?
C102 H102 0.9800 . ?
C103 O102 1.225(14) . ?
C103 N102 1.338(14) . ?
C103 C104 1.511(16) . ?
C104 N103 1.461(16) . ?
C104 C107 1.543(17) . ?
C104 H104 0.9800 . ?
C105 O103 1.234(14) . ?
C105 N103 1.319(15) . ?
C105 C106 1.532(16) . ?
C106 N101 1.467(15) . ?
C106 C107 1.521(19) . ?
C106 H106 0.9800 . ?
C107 H107 0.9800 . ?
N101 H11A 0.8600 . ?
N102 H12A 0.8600 . ?
N103 H13A 0.8600 . ?
C201 C202 1.40(3) . ?
C201 H20A 0.9600 . ?
C201 H20B 0.9600 . ?
C201 H20C 0.9600 . ?
C202 N201 1.14(3) . ?

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 N1 127.6(12) . . ?
O1 C1 C2 123.0(12) . . ?
N1 C1 C2 109.3(11) . . ?
N2 C2 C1 109.3(11) . . ?
N2 C2 C7 105.0(10) . . ?
C1 C2 C7 104.5(10) . . ?
N2 C2 H2 112.5 . . ?
C1 C2 H2 112.5 . . ?
C7 C2 H2 112.5 . . ?
O2 C3 N2 127.9(12) . . ?
O2 C3 C4 122.9(12) . . ?
N2 C3 C4 109.2(12) . . ?
N3 C4 C3 110.6(11) . . ?
N3 C4 C7 104.6(10) . . ?
C3 C4 C7 105.2(10) . . ?
N3 C4 H4 112.0 . . ?
C3 C4 H4 112.0 . . ?
C7 C4 H4 112.0 . . ?
O3 C5 N3 127.4(12) . . ?
O3 C5 C6 124.3(11) . . ?
N3 C5 C6 108.3(11) . . ?
N1 C6 C7 104.7(10) . . ?
N1 C6 C5 109.7(11) . . ?
C7 C6 C5 105.1(10) . . ?
N1 C6 H6 112.3 . . ?
C7 C6 H6 112.3 . . ?
C5 C6 H6 112.3 . . ?
C6 C7 C2 105.7(11) . . ?
C6 C7 C4 105.9(10) . . ?
C2 C7 C4 104.9(10) . . ?
C6 C7 H7 113.2 . . ?
C2 C7 H7 113.2 . . ?
C4 C7 H7 113.2 . . ?
C1 N1 C6 115.7(11) . . ?
C1 N1 H1A 122.1 . . ?
C6 N1 H1A 122.1 . . ?
C3 N2 C2 115.5(10) . . ?
C3 N2 H2A 122.3 . . ?
C2 N2 H2A 122.3 . . ?
C5 N3 C4 115.9(11) . . ?
C5 N3 H3A 122.1 . . ?
C4 N3 H3A 122.1 . . ?
O101 C101 N101 125.7(11) . . ?
O101 C101 C102 124.8(11) . . ?
N101 C101 C102 109.4(10) . . ?
N102 C102 C101 110.8(10) . . ?
N102 C102 C107 104.1(9) . . ?
C101 C102 C107 104.0(10) . . ?
N102 C102 H102 112.4 . . ?
C101 C102 H102 112.4 . . ?
C107 C102 H102 112.4 . . ?
O102 C103 N102 125.8(11) . . ?
O102 C103 C104 125.5(10) . . ?
N102 C103 C104 108.7(10) . . ?
N103 C104 C103 111.3(10) . . ?
N103 C104 C107 103.8(9) . . ?
C103 C104 C107 105.3(9) . . ?
N103 C104 H104 112.0 . . ?
C103 C104 H104 112.0 . . ?
C107 C104 H104 112.0 . . ?
O103 C105 N103 126.9(11) . . ?
O103 C105 C106 124.4(10) . . ?
N103 C105 C106 108.7(10) . . ?
N101 C106 C107 104.4(9) . . ?
N101 C106 C105 109.8(10) . . ?
C107 C106 C105 105.3(9) . . ?
N101 C106 H106 112.3 . . ?
C107 C106 H106 112.3 . . ?
C105 C106 H106 112.3 . . ?
C106 C107 C102 107.4(10) . . ?
C106 C107 C104 106.3(10) . . ?
C102 C107 C104 105.8(9) . . ?
C106 C107 H107 112.3 . . ?
C102 C107 H107 112.3 . . ?
C104 C107 H107 112.3 . . ?
C101 N101 C106 114.8(10) . . ?
C101 N101 H11A 122.6 . . ?
C106 N101 H11A 122.6 . . ?
C103 N102 C102 116.0(10) . . ?
C103 N102 H12A 122.0 . . ?
C102 N102 H12A 122.0 . . ?
C105 N103 C104 115.9(10) . . ?
C105 N103 H13A 122.1 . . ?
C104 N103 H13A 122.1 . . ?
C202 C201 H20A 109.5 . . ?
C202 C201 H20B 109.5 . . ?
H20A C201 H20B 109.5 . . ?
C202 C201 H20C 109.5 . . ?
H20A C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
N201 C202 C201 173(3) . . ?

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
N1 H1A O103 0.86 2.06 2.889(14) 162.0 2_556
N2 H2A O102 0.86 2.12 2.966(13) 168.4 2_656
N3 H3A O101 0.86 2.06 2.918(14) 175.6 2_657
C104 H104 O101 0.98 2.60 3.385(14) 136.9 2_556
C106 H106 O102 0.98 2.63 3.432(15) 138.6 2_556
N101 H11A O1 0.86 1.99 2.815(15) 160.7 2_546
N102 H12A O3 0.86 1.99 2.828(14) 165.9 2_647
N103 H13A O2 0.86 1.92 2.778(13) 171.6 2_646
N1 H1A O103 0.86 2.06 2.889(14) 162.0 2_556
N2 H2A O102 0.86 2.12 2.966(13) 168.4 2_656
N3 H3A O101 0.86 2.06 2.918(14) 175.6 2_657
C104 H104 O101 0.98 2.60 3.385(14) 136.9 2_556
C106 H106 O102 0.98 2.63 3.432(15) 138.6 2_556
N101 H11A O1 0.86 1.99 2.815(15) 160.7 2_546
N102 H12A O3 0.86 1.99 2.828(14) 165.9 2_647
N103 H13A O2 0.86 1.92 2.778(13) 171.6 2_646

_refine_diff_density_max         1.507
_refine_diff_density_min         -1.209
_refine_diff_density_rms         0.320

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2128470'
loop_
_audit_author_name
_audit_author_address
'Daniel Strand' 'Lund University'
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
(2aS*,4aS*,6aS*)-hexahydro-1,3,5-triazacyclopenta[cd]pentalene-2,4,6(1H)-trione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 D3 N3 O3'
_chemical_formula_sum            'C7 H4 D3 N3 O3'
_chemical_formula_weight         184.17

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'
D D 0.0000 0.0000 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.2905(7)
_cell_length_b                   11.3194(9)
_cell_length_c                   9.0781(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.738(12)
_cell_angle_gamma                90
_cell_volume                     695.89(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1190
_cell_measurement_theta_min      4.3020
_cell_measurement_theta_max      26.9730

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.96066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.0433
_diffrn_reflns_number            4010
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.506
_diffrn_reflns_theta_max         29.436
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1622
_reflns_number_gt                1206
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0451P)²+0.1051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1622
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1184
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.4817(3) 0.68721(16) 1.0133(2) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.3157(3) 0.63812(15) 0.8689(2) 0.0268(4) Uani 1 1 d . . . . .
H4 H 0.365709 0.582239 0.810173 0.032 Uiso 1 1 calc R U . . .
C3 C -0.0115(3) 0.64547(16) 0.8593(2) 0.0267(4) Uani 1 1 d . . . . .
C4 C 0.0116(3) 0.75474(14) 0.7693(2) 0.0256(4) Uani 1 1 d . . . . .
H3 H -0.088726 0.757568 0.661762 0.031 Uiso 1 1 calc R U . . .
C5 C 0.1846(3) 0.92227(16) 0.9054(2) 0.0258(4) Uani 1 1 d . . . . .
C6 C 0.3340(3) 0.85433(15) 0.8588(2) 0.0284(4) Uani 1 1 d . . . . .
H2 H 0.389156 0.902083 0.795081 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2203(3) 0.74627(14) 0.7677(2) 0.0264(4) Uani 1 1 d . . . . .
H1 H 0.220572 0.741255 0.659989 0.032 Uiso 1 1 calc R U . . .
N1 N 0.4857(2) 0.80510(14) 0.9980(2) 0.0339(4) Uani 1 1 d . . . . .
N2 N 0.1591(2) 0.58646(14) 0.91016(19) 0.0282(4) Uani 1 1 d . . . . .
N3 N 0.0139(2) 0.86299(13) 0.85715(19) 0.0277(4) Uani 1 1 d . . . . .
O1 O 0.5887(2) 0.62884(12) 1.12505(17) 0.0387(4) Uani 1 1 d . . . . .
O2 O -0.1621(2) 0.61782(12) 0.88163(18) 0.0419(4) Uani 1 1 d . . . . .
O3 O 0.2190(2) 1.01594(12) 0.97953(17) 0.0389(4) Uani 1 1 d . . . . .
D1 D -0.088(3) 0.889(2) 0.870(3) 0.047 Uiso 1 1 d . U . . .
D2 D 0.587(3) 0.8513(19) 1.060(3) 0.047 Uiso 1 1 d . U . . .
D3 D 0.175(3) 0.525(2) 0.962(3) 0.047 Uiso 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
C1 O1 1.220(2) . ?
C1 N1 1.343(2) . ?
C1 C2 1.522(3) . ?
C2 N2 1.451(2) . ?
C2 C7 1.534(2) . ?
C2 H4 0.9800 . ?
C3 O2 1.229(2) . ?
C3 N2 1.334(2) . ?
C3 C4 1.525(2) . ?
C4 N3 1.459(2) . ?
C4 C7 1.530(3) . ?
C4 H3 0.9800 . ?
C5 O3 1.231(2) . ?
C5 N3 1.337(2) . ?
C5 C6 1.516(2) . ?
C6 N1 1.448(2) . ?
C6 C7 1.536(2) . ?
C6 H2 0.9800 . ?
C7 H1 0.9800 . ?
N1 D2 0.91(2) . ?
N2 D3 0.82(2) . ?
N3 D1 0.85(2) . ?

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 N1 126.33(18) . . ?
O1 C1 C2 125.33(17) . . ?
N1 C1 C2 108.32(16) . . ?
N2 C2 C1 112.03(15) . . ?
N2 C2 C7 104.51(15) . . ?
C1 C2 C7 105.32(14) . . ?
N2 C2 H4 111.5 . . ?
C1 C2 H4 111.5 . . ?
C7 C2 H4 111.5 . . ?
O2 C3 N2 126.19(17) . . ?
O2 C3 C4 125.26(17) . . ?
N2 C3 C4 108.54(16) . . ?
N3 C4 C3 111.70(15) . . ?
N3 C4 C7 104.36(14) . . ?
C3 C4 C7 105.16(14) . . ?
N3 C4 H3 111.7 . . ?
C3 C4 H3 111.7 . . ?
C7 C4 H3 111.7 . . ?
O3 C5 N3 126.01(18) . . ?
O3 C5 C6 124.60(17) . . ?
N3 C5 C6 109.37(16) . . ?
N1 C6 C5 110.30(15) . . ?
N1 C6 C7 104.42(14) . . ?
C5 C6 C7 104.72(15) . . ?
N1 C6 H2 112.3 . . ?
C5 C6 H2 112.3 . . ?
C7 C6 H2 112.3 . . ?
C4 C7 C2 106.05(14) . . ?
C4 C7 C6 106.57(14) . . ?
C2 C7 C6 106.17(15) . . ?
C4 C7 H1 112.5 . . ?
C2 C7 H1 112.5 . . ?
C6 C7 H1 112.5 . . ?
C1 N1 C6 115.71(16) . . ?
C1 N1 D2 123.5(14) . . ?
C6 N1 D2 120.0(14) . . ?
C3 N2 C2 115.51(16) . . ?
C3 N2 D3 122.4(17) . . ?
C2 N2 D3 122.1(17) . . ?
C5 N3 C4 114.93(16) . . ?
C5 N3 D1 122.6(16) . . ?
C4 N3 D1 122.3(16) . . ?

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
C2 H4 O1 0.98 2.45 3.097(2) 122.9 3_667
C4 H3 O1 0.98 2.59 3.157(2) 116.8 4_475
C6 H2 O1 0.98 2.51 3.302(2) 138.1 4_575
N3 D1 O1 0.85(2) 2.58(2) 3.036(2) 114.7(17) 4_475
N3 D1 O3 0.85(2) 2.21(2) 2.970(2) 149(2) 3_577
N1 D2 O3 0.91(2) 2.18(2) 2.908(2) 136.3(18) 3_677
N2 D3 O2 0.82(2) 2.18(2) 2.981(2) 166(2) 3_567

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.054

