# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc23w83d
_database_code_depnum_ccdc_archive 'CCDC 1962613'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2019-10-31 deposited with the CCDC.	2020-02-12 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         ?
_chemical_formula_sum            'C14 H17 N3 O5'
_chemical_formula_weight         307.30

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/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                   7.17630(10)
_cell_length_b                   28.9373(4)
_cell_length_c                   7.06700(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.1860(10)
_cell_angle_gamma                90
_cell_volume                     1466.48(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130.0(2)
_cell_measurement_reflns_used    8360
_cell_measurement_theta_min      4.5740
_cell_measurement_theta_max      73.0989

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.902
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.76430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0711
_diffrn_reflns_number            10358
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         6.117
_diffrn_reflns_theta_max         79.461
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2902
_reflns_number_gt                2689
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
;
_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)+(0.0570P)²+0.7426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0014(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2902
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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 0.46974(13) 0.17118(3) 0.12961(15) 0.0225(3) Uani 1 1 d . . . . .
C10 C 0.61383(19) 0.24401(5) 0.07210(19) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.4512(2) 0.31356(5) 0.14552(19) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.29813(19) 0.24149(5) 0.2015(2) 0.0211(3) Uani 1 1 d . . . . .
H14 H 0.196116 0.224744 0.241143 0.025 Uiso 1 1 calc R U . . .
C9 C 0.45784(19) 0.21762(5) 0.13575(19) 0.0186(3) Uani 1 1 d . . . . .
O5 O 0.30507(17) 0.38308(4) 0.20952(17) 0.0346(3) Uani 1 1 d . . . . .
O2 O 0.80021(18) 0.18126(4) -0.0100(2) 0.0483(4) Uani 1 1 d . . . . .
N3 N 0.44974(19) 0.36402(4) 0.15574(18) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.29396(16) 0.14994(4) 0.19362(18) 0.0232(3) Uani 1 1 d . . . . .
N2 N 0.78547(16) 0.22284(4) -0.00651(18) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.59270(19) 0.38471(4) 0.1109(2) 0.0451(4) Uani 1 1 d . . . . .
C11 C 0.6104(2) 0.29184(5) 0.07760(19) 0.0212(3) Uani 1 1 d . . . . .
H11 H 0.710796 0.309105 0.037428 0.025 Uiso 1 1 calc R U . . .
C1 C 0.3047(2) 0.10623(5) 0.1790(2) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.1221(2) 0.08077(5) 0.2275(2) 0.0277(4) Uani 1 1 d . . . . .
C13 C 0.2942(2) 0.28889(5) 0.2066(2) 0.0219(3) Uani 1 1 d . . . . .
H13 H 0.190543 0.304463 0.249394 0.026 Uiso 1 1 calc R U . . .
O3 O 0.90563(17) 0.24854(4) -0.0726(2) 0.0416(3) Uani 1 1 d . . . . .
C6 C 0.4716(2) 0.07836(5) 0.1125(2) 0.0280(4) Uani 1 1 d . . . . .
H6A H 0.448702 0.068398 -0.017330 0.034 Uiso 1 1 calc R U . . .
H6B H 0.582754 0.097457 0.117649 0.034 Uiso 1 1 calc R U . . .
C8 C -0.0169(2) 0.11080(6) 0.3407(3) 0.0369(4) Uani 1 1 d . . . . .
H8A H 0.039905 0.118973 0.461305 0.055 Uiso 1 1 calc R U . . .
H8B H -0.047150 0.138375 0.270601 0.055 Uiso 1 1 calc R U . . .
H8C H -0.128669 0.093449 0.359774 0.055 Uiso 1 1 calc R U . . .
C5 C 0.5001(2) 0.03643(6) 0.2407(3) 0.0345(4) Uani 1 1 d . . . . .
H5A H 0.544555 0.046812 0.364871 0.041 Uiso 1 1 calc R U . . .
H5B H 0.595932 0.016918 0.189537 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3231(3) 0.00772(6) 0.2622(3) 0.0377(4) Uani 1 1 d . . . . .
H4A H 0.350414 -0.018217 0.345680 0.045 Uiso 1 1 calc R U . . .
H4B H 0.282429 -0.004472 0.139595 0.045 Uiso 1 1 calc R U . . .
C7 C 0.0362(2) 0.06757(6) 0.0384(2) 0.0335(4) Uani 1 1 d . . . . .
H7A H 0.009805 0.094961 -0.034458 0.050 Uiso 1 1 calc R U . . .
H7B H 0.121242 0.048358 -0.027697 0.050 Uiso 1 1 calc R U . . .
H7C H -0.077584 0.050935 0.056211 0.050 Uiso 1 1 calc R U . . .
C3 C 0.1643(3) 0.03714(6) 0.3440(2) 0.0365(4) Uani 1 1 d . . . . .
H3A H 0.052191 0.018476 0.347818 0.044 Uiso 1 1 calc R U . . .
H3B H 0.199306 0.045967 0.472915 0.044 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 C9 1.3472(17) . ?
O1 N1 1.4890(15) . ?
C10 C11 1.385(2) . ?
C10 C9 1.4412(19) . ?
C10 N2 1.5011(18) . ?
C12 C11 1.405(2) . ?
C12 C13 1.415(2) . ?
C12 N3 1.4620(19) . ?
C14 C13 1.372(2) . ?
C14 C9 1.431(2) . ?
O5 N3 1.2477(18) . ?
O2 N2 1.2083(18) . ?
N3 O4 1.2394(18) . ?
N1 C1 1.272(2) . ?
N2 O3 1.2432(17) . ?
C1 C6 1.533(2) . ?
C1 C2 1.553(2) . ?
C2 C7 1.500(2) . ?
C2 C3 1.531(2) . ?
C2 C8 1.566(2) . ?
C6 C5 1.523(2) . ?
C5 C4 1.530(3) . ?
C4 C3 1.552(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
C9 O1 N1 110.27(10) . . ?
C11 C10 C9 120.40(13) . . ?
C11 C10 N2 115.72(12) . . ?
C9 C10 N2 123.87(13) . . ?
C11 C12 C13 123.08(13) . . ?
C11 C12 N3 118.11(13) . . ?
C13 C12 N3 118.80(13) . . ?
C13 C14 C9 120.57(13) . . ?
O1 C9 C14 122.99(12) . . ?
O1 C9 C10 117.88(12) . . ?
C14 C9 C10 119.13(13) . . ?
O4 N3 O5 124.80(13) . . ?
O4 N3 C12 117.55(13) . . ?
O5 N3 C12 117.65(13) . . ?
C1 N1 O1 109.35(11) . . ?
O2 N2 O3 121.71(13) . . ?
O2 N2 C10 119.18(12) . . ?
O3 N2 C10 119.05(13) . . ?
C10 C11 C12 118.19(13) . . ?
N1 C1 C6 126.79(13) . . ?
N1 C1 C2 113.56(13) . . ?
C6 C1 C2 119.59(13) . . ?
C7 C2 C3 109.60(13) . . ?
C7 C2 C1 104.23(12) . . ?
C3 C2 C1 111.02(13) . . ?
C7 C2 C8 110.41(14) . . ?
C3 C2 C8 107.42(14) . . ?
C1 C2 C8 114.13(13) . . ?
C14 C13 C12 118.61(13) . . ?
C5 C6 C1 109.03(14) . . ?
C6 C5 C4 113.47(13) . . ?
C5 C4 C3 111.31(14) . . ?
C2 C3 C4 112.63(14) . . ?

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 O1 C9 C14 1.88(17) . . . . ?
N1 O1 C9 C10 -177.90(11) . . . . ?
C13 C14 C9 O1 179.31(12) . . . . ?
C13 C14 C9 C10 -0.92(19) . . . . ?
C11 C10 C9 O1 -179.13(12) . . . . ?
N2 C10 C9 O1 2.15(19) . . . . ?
C11 C10 C9 C14 1.09(19) . . . . ?
N2 C10 C9 C14 -177.63(12) . . . . ?
C11 C12 N3 O4 -2.9(2) . . . . ?
C13 C12 N3 O4 176.24(13) . . . . ?
C11 C12 N3 O5 177.38(12) . . . . ?
C13 C12 N3 O5 -3.51(19) . . . . ?
C9 O1 N1 C1 177.16(12) . . . . ?
C11 C10 N2 O2 177.72(14) . . . . ?
C9 C10 N2 O2 -3.5(2) . . . . ?
C11 C10 N2 O3 -4.85(18) . . . . ?
C9 C10 N2 O3 173.93(13) . . . . ?
C9 C10 C11 C12 -0.35(19) . . . . ?
N2 C10 C11 C12 178.47(11) . . . . ?
C13 C12 C11 C10 -0.6(2) . . . . ?
N3 C12 C11 C10 178.47(12) . . . . ?
O1 N1 C1 C6 1.77(19) . . . . ?
O1 N1 C1 C2 -175.51(11) . . . . ?
N1 C1 C2 C7 103.24(15) . . . . ?
C6 C1 C2 C7 -74.25(17) . . . . ?
N1 C1 C2 C3 -138.84(14) . . . . ?
C6 C1 C2 C3 43.66(18) . . . . ?
N1 C1 C2 C8 -17.27(19) . . . . ?
C6 C1 C2 C8 165.24(14) . . . . ?
C9 C14 C13 C12 0.0(2) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
N3 C12 C13 C14 -178.30(12) . . . . ?
N1 C1 C6 C5 137.23(15) . . . . ?
C2 C1 C6 C5 -45.63(18) . . . . ?
C1 C6 C5 C4 51.82(18) . . . . ?
C6 C5 C4 C3 -58.68(19) . . . . ?
C7 C2 C3 C4 68.55(18) . . . . ?
C1 C2 C3 C4 -46.04(18) . . . . ?
C8 C2 C3 C4 -171.47(13) . . . . ?
C5 C4 C3 C2 55.01(18) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_cmpd3
_database_code_depnum_ccdc_archive 'CCDC 1973699'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2020-01-30 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_audit_creation_date             2020-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 N3 O5'
_chemical_formula_sum            'C9 H9 N3 O5'
_chemical_formula_weight         239.19
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'

_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                   5.49110(10)
_cell_length_b                   10.5173(2)
_cell_length_c                   18.2619(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1054.65(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13003
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      51.0780
_cell_measurement_theta_min      3.6980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 26 0.0324
0 15 5 0.1756
1 1 -26 0.1062
3 0 24 0.0450
2 11 -16 0.1265
8 1 0 0.2003
-6 0 -15 0.1012
0 -10 -19 0.1095
-1 9 -20 0.1034

_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.144
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0780 -0.4994 25.7328 0.9996 -0.0258 0.0089
0.2410 14.5359 4.9967 0.1573 0.2044 0.9662
0.8721 0.7903 -25.5477 -0.9915 0.1301 -0.0077
3.0799 0.0490 23.6251 0.9233 0.3829 -0.0311
2.0531 10.8571 -16.1503 -0.6500 0.3983 0.6473
7.7044 1.4585 0.3287 0.0257 0.9964 -0.0809
-6.2301 -0.3336 -15.2794 -0.6055 -0.7898 0.0981
0.4108 -9.7101 -19.4083 -0.7274 -0.0578 -0.6837
-1.3983 8.7685 -20.2334 -0.8105 -0.0639 0.5822

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            24292
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         51.205
_diffrn_reflns_theta_min         2.954
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00 -11.00   0.50   10.00    --    0.47 -19.00 -60.00   50
  2  ω      1.00  33.00   0.50   10.00    --    0.47 -99.00-120.00   64
  3  ω     -6.00  36.00   0.50   15.00    --   55.35 -57.00  60.00   84
  4  ω      4.00  30.00   0.50   15.00    --   55.35 -57.00  90.00   52
  5  ω    -17.00  10.00   0.50   15.00    --   55.35 -37.00 150.00   54
  6  ω    101.00 128.00   0.50   15.00    --   55.35  77.00 -30.00   54
  7  ω    -13.00  13.00   0.50   15.00    --  -54.42  57.00 150.00   52
  8  ω    -62.00 -28.00   0.50   15.00    --  -54.42  57.00 150.00   68
  9  ω    -94.00 -36.00   0.50   15.00    --  -54.42 114.00 134.00  116
 10  ω   -121.00 -42.00   0.50   15.00    --  -54.42 -14.00-163.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0021631000
_diffrn_orient_matrix_UB_12      -0.0025519000
_diffrn_orient_matrix_UB_13      0.0388035000
_diffrn_orient_matrix_UB_21      0.1270549000
_diffrn_orient_matrix_UB_22      0.0120872000
_diffrn_orient_matrix_UB_23      -0.0003821000
_diffrn_orient_matrix_UB_31      -0.0231269000
_diffrn_orient_matrix_UB_32      0.0663137000
_diffrn_orient_matrix_UB_33      0.0015620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                9009
_reflns_number_total             10696
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     49.99
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 3240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         10696
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0581P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C3(H3)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.25888(9) 0.40789(4) 0.60723(3) 0.01559(8) Uani 1 1 d . . . . .
O4 O 0.77958(11) 0.91152(5) 0.69661(4) 0.02250(10) Uani 1 1 d . . . . .
O3 O 0.08937(10) 0.76067(5) 0.55668(3) 0.01967(9) Uani 1 1 d . . . . .
O5 O 1.04566(10) 0.77575(6) 0.73647(3) 0.02282(10) Uani 1 1 d . . . . .
O2 O 0.13361(14) 0.57519(5) 0.50633(4) 0.02725(14) Uani 1 1 d . . . . .
N2 N 0.18354(10) 0.65487(5) 0.55302(3) 0.01492(8) Uani 1 1 d . . . . .
N3 N 0.85386(10) 0.80226(5) 0.70543(3) 0.01620(8) Uani 1 1 d . . . . .
N1 N 0.34422(10) 0.28132(5) 0.62497(3) 0.01502(8) Uani 1 1 d . . . . .
C5 C 0.76281(11) 0.57399(6) 0.69849(4) 0.01525(9) Uani 1 1 d . . . . .
H5 H 0.901232 0.557631 0.728233 0.018 Uiso 1 1 calc R U . . .
C6 C 0.61629(12) 0.47501(6) 0.67525(4) 0.01524(9) Uani 1 1 d . . . . .
H6 H 0.650631 0.390631 0.690684 0.018 Uiso 1 1 calc R U . . .
C4 C 0.70555(11) 0.69790(5) 0.67787(3) 0.01328(8) Uani 1 1 d . . . . .
C1 C 0.41732(10) 0.49835(5) 0.62904(3) 0.01239(8) Uani 1 1 d . . . . .
C3 C 0.51276(11) 0.72507(5) 0.63182(3) 0.01292(8) Uani 1 1 d . . . . .
H3 H 0.476252 0.810128 0.618182 0.015 Uiso 1 1 calc R U . . .
C2 C 0.37443(10) 0.62432(5) 0.60618(3) 0.01203(7) Uani 1 1 d . . . . .
C7 C 0.18982(11) 0.19900(5) 0.60213(3) 0.01384(8) Uani 1 1 d . . . . .
C8 C -0.04774(14) 0.22627(7) 0.56587(5) 0.02222(13) Uani 1 1 d . . . . .
H8A H -0.174427 0.236563 0.603203 0.033 Uiso 1 1 calc R U . . .
H8B H -0.090755 0.155529 0.533429 0.033 Uiso 1 1 calc R U . . .
H8C H -0.034211 0.304660 0.537144 0.033 Uiso 1 1 calc R U . . .
C9 C 0.26203(15) 0.06326(6) 0.61271(4) 0.02025(11) Uani 1 1 d . . . . .
H9A H 0.283392 0.022605 0.564856 0.030 Uiso 1 1 calc R U . . .
H9B H 0.134619 0.018728 0.640177 0.030 Uiso 1 1 calc R U . . .
H9C H 0.415444 0.059422 0.640044 0.030 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 N1 1.4480(6) . ?
O1 C1 1.3494(7) . ?
O4 N3 1.2299(8) . ?
O3 N2 1.2288(7) . ?
O5 N3 1.2281(8) . ?
O2 N2 1.2265(8) . ?
N2 C2 1.4643(7) . ?
N3 C4 1.4565(8) . ?
N1 C7 1.2816(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.3825(8) . ?
C5 C4 1.3924(8) . ?
C6 H6 0.9500 . ?
C6 C1 1.4022(8) . ?
C4 C3 1.3819(8) . ?
C1 C2 1.4088(8) . ?
C3 H3 0.9500 . ?
C3 C2 1.3853(8) . ?
C7 C8 1.4908(10) . ?
C7 C9 1.4942(8) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C1 O1 N1 111.93(4) . . ?
O3 N2 C2 117.64(5) . . ?
O2 N2 O3 124.22(6) . . ?
O2 N2 C2 118.09(5) . . ?
O4 N3 C4 118.26(6) . . ?
O5 N3 O4 123.85(6) . . ?
O5 N3 C4 117.90(6) . . ?
C7 N1 O1 109.52(5) . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.37(5) . . ?
C4 C5 H5 120.3 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C1 120.42(5) . . ?
C1 C6 H6 119.8 . . ?
C5 C4 N3 119.06(5) . . ?
C3 C4 N3 118.87(5) . . ?
C3 C4 C5 122.08(5) . . ?
O1 C1 C6 123.82(5) . . ?
O1 C1 C2 117.89(5) . . ?
C6 C1 C2 118.24(5) . . ?
C4 C3 H3 121.1 . . ?
C4 C3 C2 117.88(5) . . ?
C2 C3 H3 121.1 . . ?
C1 C2 N2 121.49(5) . . ?
C3 C2 N2 116.66(5) . . ?
C3 C2 C1 121.83(5) . . ?
N1 C7 C8 126.40(6) . . ?
N1 C7 C9 115.33(6) . . ?
C8 C7 C9 118.26(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 N1 C7 C8 -2.65(10) . . . . ?
O1 N1 C7 C9 176.40(5) . . . . ?
O1 C1 C2 N2 -7.68(9) . . . . ?
O1 C1 C2 C3 173.39(6) . . . . ?
O4 N3 C4 C5 -168.59(6) . . . . ?
O4 N3 C4 C3 11.64(9) . . . . ?
O3 N2 C2 C1 151.43(6) . . . . ?
O3 N2 C2 C3 -29.59(8) . . . . ?
O5 N3 C4 C5 11.08(9) . . . . ?
O5 N3 C4 C3 -168.68(6) . . . . ?
O2 N2 C2 C1 -30.95(9) . . . . ?
O2 N2 C2 C3 148.04(7) . . . . ?
N3 C4 C3 C2 179.90(5) . . . . ?
N1 O1 C1 C6 -11.31(9) . . . . ?
N1 O1 C1 C2 171.18(5) . . . . ?
C5 C6 C1 O1 -176.37(6) . . . . ?
C5 C6 C1 C2 1.12(10) . . . . ?
C5 C4 C3 C2 0.14(9) . . . . ?
C6 C5 C4 N3 177.08(6) . . . . ?
C6 C5 C4 C3 -3.16(10) . . . . ?
C6 C1 C2 N2 174.67(6) . . . . ?
C6 C1 C2 C3 -4.26(9) . . . . ?
C4 C5 C6 C1 2.46(10) . . . . ?
C4 C3 C2 N2 -175.36(6) . . . . ?
C4 C3 C2 C1 3.62(9) . . . . ?
C1 O1 N1 C7 -178.94(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.692
####################################################################### 
# 
# 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_cmpd2
_database_code_depnum_ccdc_archive 'CCDC 1973698'
loop_
_audit_author_name
_audit_author_address
'Jonathan White'
;University of Melbourne
Australia
;
_audit_update_record             
;
2020-01-30 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
_audit_creation_date             2020-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N3 O5'
_chemical_formula_sum            'C12 H13 N3 O5'
_chemical_formula_weight         279.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H13 N3 O5 '
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'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.66740(10)
_cell_length_b                   16.3925(3)
_cell_length_c                   11.6108(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.0310(10)
_cell_angle_gamma                90
_cell_volume                     1245.56(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25403
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      51.0610
_cell_measurement_theta_min      3.5020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.504
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0332
1 9 -15 0.1006
9 -1 4 0.2141
5 19 4 0.1378
2 23 -2 0.0728
2 18 -10 0.0966
0 -1 -16 0.1159
0 1 16 0.1172
-9 -1 4 0.1617
0 22 6 0.0830
4 11 11 0.1558
-2 22 2 0.0974

_exptl_crystal_size_max          0.445
_exptl_crystal_size_mid          0.235
_exptl_crystal_size_min          0.118
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 -0.9989 -0.0003 0.0413 0.0092 -0.0090
1.0113 8.9060 -15.0608 -0.0936 -0.7162 0.6916
8.5451 -0.8562 3.8286 -0.0585 -0.4420 -0.8951
4.6710 18.5209 3.8037 -0.8480 -0.3518 -0.3964
1.5243 22.7355 -1.7020 -0.9122 -0.3782 0.1575
2.2238 17.6062 -10.4231 -0.5417 -0.7065 0.4554
-0.0117 -0.6677 -16.0596 0.3231 -0.5947 0.7361
0.1044 0.5853 16.0293 -0.3194 0.5879 -0.7432
-9.3797 -1.4348 3.5079 0.0204 0.7958 0.6052
-0.1462 21.6238 5.7121 -0.9981 0.0257 -0.0558
4.2198 10.6980 10.8837 -0.6538 0.0166 -0.7565
-2.1762 22.3879 2.1125 -0.9579 0.0248 0.2861

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51580
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         51.319
_diffrn_reflns_theta_min         3.508
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  19.00   0.50   45.00    --   55.36 -57.00  30.00   70
  2  ω     47.00  73.00   0.50   45.00    --   55.36-110.00 -35.00   52
  3  ω    -14.00  12.00   0.50   45.00    --   55.36 -37.00 -30.00   52
  4  ω    -15.00  12.00   0.50   45.00    --   55.36 -37.00  30.00   54
  5  ω    -18.00   7.00   0.50   45.00    --   55.36 -37.00   0.00   50
  6  ω    -13.00  20.00   0.50   45.00    --   55.36 -57.00  60.00   66
  7  ω    -16.00  39.00   0.50   45.00    --   55.36 -57.00 -90.00  110
  8  ω     -3.00  23.00   0.50   15.00    --    0.47  77.00-150.00   52
  9  ω    101.00 126.00   0.50   45.00    --   55.36  77.00   0.00   50
 10  ω    101.00 126.00   0.50   45.00    --   55.36  77.00  90.00   50
 11  ω    101.00 126.00   0.50   45.00    --   55.36  77.00-180.00   50
 12  ω    -93.00 -24.00   0.50   45.00    --  -54.43 110.00  59.00  138
 13  ω   -114.00 -89.00   0.50   45.00    --  -54.43 -57.00 -60.00   50
 14  ω   -115.00 -88.00   0.50   45.00    --  -54.43 -57.00   0.00   54
 15  ω   -126.00 -82.00   0.50   45.00    --  -54.43 -57.00  60.00   88
 16  ω   -118.00 -82.00   0.50   45.00    --  -54.43 -57.00 120.00   72
 17  ω    -89.00 -43.00   0.50   45.00    --  -54.43 125.00 -30.00   92
 18  ω   -102.00 -34.00   0.50   45.00    --  -54.43 125.00-150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0027403000
_diffrn_orient_matrix_UB_12      -0.0413163000
_diffrn_orient_matrix_UB_13      -0.0183991000
_diffrn_orient_matrix_UB_21      -0.0694297000
_diffrn_orient_matrix_UB_22      -0.0091768000
_diffrn_orient_matrix_UB_23      0.0374652000
_diffrn_orient_matrix_UB_31      -0.0831661000
_diffrn_orient_matrix_UB_32      0.0090485000
_diffrn_orient_matrix_UB_33      -0.0461535000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                20837
_reflns_number_total             25111
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     47.63
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 8110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         25111
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1153
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9A(H9AA,H9AB), C12A(H12A,H12B), C11A(H11A,H11B), C8(H8A,H8B), C8A(H8AA,H8AB),
  C12(H12C,H12D), C10A(H10A,H10B), C9(H9A,H9B), C10(H10C,H10D), C11(H11C,H11D)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5A(H5A), C3A(H3A), C5(H5), C6A(H6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1A O 0.07229(8) 0.61769(4) 0.48558(4) 0.01514(8) Uani 1 1 d . . . . .
O5A O 0.70527(9) 0.71201(4) 0.17261(5) 0.02008(10) Uani 1 1 d . . . . .
O1 O 0.56072(9) 0.38501(4) 0.76652(4) 0.01655(8) Uani 1 1 d . . . . .
O4A O 0.46718(10) 0.65702(5) 0.04249(5) 0.02210(11) Uani 1 1 d . . . . .
O4 O 0.95546(11) 0.34303(5) 0.32277(5) 0.02334(11) Uani 1 1 d . . . . .
O5 O 1.19196(9) 0.28763(4) 0.45341(5) 0.01907(9) Uani 1 1 d . . . . .
O3A O -0.11470(11) 0.54102(5) 0.14779(5) 0.02531(12) Uani 1 1 d . . . . .
O2A O -0.17281(10) 0.54262(5) 0.32448(6) 0.02319(11) Uani 1 1 d . . . . .
O2 O 0.30780(10) 0.45329(5) 0.60334(5) 0.02210(11) Uani 1 1 d . . . . .
O3 O 0.36787(11) 0.45646(5) 0.42668(5) 0.02455(12) Uani 1 1 d . . . . .
N1A N 0.16454(9) 0.64832(4) 0.60093(5) 0.01473(8) Uani 1 1 d . . . . .
N2A N -0.06776(9) 0.55942(4) 0.25223(5) 0.01541(8) Uani 1 1 d . . . . .
N3A N 0.54037(9) 0.67675(4) 0.14375(5) 0.01551(8) Uani 1 1 d . . . . .
N2 N 0.41433(9) 0.43793(4) 0.53089(5) 0.01488(8) Uani 1 1 d . . . . .
N3 N 1.02698(9) 0.32295(4) 0.42375(5) 0.01562(9) Uani 1 1 d . . . . .
N1 N 0.65121(10) 0.35278(4) 0.88156(5) 0.01654(9) Uani 1 1 d . . . . .
C2 C 0.60822(10) 0.39449(4) 0.56906(5) 0.01272(8) Uani 1 1 d . . . . .
C3 C 0.72260(10) 0.37977(4) 0.48286(5) 0.01375(9) Uani 1 1 d . . . . .
H3 H 0.673759 0.396113 0.403978 0.016 Uiso 1 1 calc R U . . .
C4A C 0.42388(10) 0.65839(4) 0.23484(5) 0.01372(9) Uani 1 1 d . . . . .
C1A C 0.19292(10) 0.62954(4) 0.40695(5) 0.01252(8) Uani 1 1 d . . . . .
C6 C 0.87129(10) 0.33287(4) 0.71527(6) 0.01441(9) Uani 1 1 d . . . . .
H6 H 0.923458 0.317309 0.794131 0.017 Uiso 1 1 calc R U . . .
C4 C 0.90900(10) 0.34082(4) 0.51447(6) 0.01371(9) Uani 1 1 d . . . . .
C2A C 0.12367(10) 0.60428(4) 0.28985(5) 0.01272(8) Uani 1 1 d . . . . .
C7A C 0.06623(10) 0.62114(4) 0.67726(5) 0.01372(8) Uani 1 1 d . . . . .
C5A C 0.50184(10) 0.68019(4) 0.35057(6) 0.01489(9) Uani 1 1 d . . . . .
H5A H 0.633275 0.704434 0.370931 0.018 Uiso 1 1 calc R U . . .
C3A C 0.23757(10) 0.61964(4) 0.20386(5) 0.01365(8) Uani 1 1 d . . . . .
H3A H 0.188016 0.603719 0.124872 0.016 Uiso 1 1 calc R U . . .
C9A C -0.01970(12) 0.67481(5) 0.86465(6) 0.01781(10) Uani 1 1 d . . . . .
H9AA H 0.038118 0.683989 0.948724 0.021 Uiso 1 1 calc R U . . .
H9AB H -0.076203 0.727214 0.830464 0.021 Uiso 1 1 calc R U . . .
C5 C 0.98580(10) 0.31848(4) 0.62999(6) 0.01478(9) Uani 1 1 d . . . . .
H5 H 1.116325 0.293454 0.650174 0.018 Uiso 1 1 calc R U . . .
C6A C 0.38662(10) 0.66629(4) 0.43554(5) 0.01454(9) Uani 1 1 d . . . . .
H6A H 0.438915 0.681770 0.514417 0.017 Uiso 1 1 calc R U . . .
C12A C -0.11713(13) 0.56632(5) 0.65643(7) 0.02041(12) Uani 1 1 d . . . . .
H12A H -0.075006 0.510251 0.682046 0.024 Uiso 1 1 calc R U . . .
H12B H -0.175907 0.564657 0.571440 0.024 Uiso 1 1 calc R U . . .
C11A C -0.28001(12) 0.59633(6) 0.72369(7) 0.02057(12) Uani 1 1 d . . . . .
H11A H -0.340989 0.647529 0.687613 0.025 Uiso 1 1 calc R U . . .
H11B H -0.390154 0.555122 0.717243 0.025 Uiso 1 1 calc R U . . .
C1 C 0.67829(10) 0.37031(4) 0.68667(5) 0.01299(8) Uani 1 1 d . . . . .
C8 C 0.64175(12) 0.35610(5) 1.08291(6) 0.01749(10) Uani 1 1 d . . . . .
H8A H 0.720002 0.400760 1.128239 0.021 Uiso 1 1 calc R U . . .
H8B H 0.735387 0.309350 1.081872 0.021 Uiso 1 1 calc R U . . .
C7 C 0.56304(11) 0.38423(4) 0.95959(6) 0.01514(9) Uani 1 1 d . . . . .
C8A C 0.15012(11) 0.64608(5) 0.80154(6) 0.01622(10) Uani 1 1 d . . . . .
H8AA H 0.250172 0.690729 0.801723 0.019 Uiso 1 1 calc R U . . .
H8AB H 0.222638 0.599266 0.844590 0.019 Uiso 1 1 calc R U . . .
C12 C 0.39397(16) 0.44575(6) 0.94188(7) 0.02515(16) Uani 1 1 d . . . . .
H12C H 0.336896 0.451300 0.857030 0.030 Uiso 1 1 calc R U . . .
H12D H 0.448589 0.499507 0.971586 0.030 Uiso 1 1 calc R U . . .
C10A C -0.19072(12) 0.61148(5) 0.85300(6) 0.01912(11) Uani 1 1 d . . . . .
H10A H -0.136078 0.559821 0.890651 0.023 Uiso 1 1 calc R U . . .
H10B H -0.299367 0.631270 0.893407 0.023 Uiso 1 1 calc R U . . .
C9 C 0.46570(13) 0.33045(5) 1.14289(7) 0.01912(11) Uani 1 1 d . . . . .
H9A H 0.400094 0.280633 1.104782 0.023 Uiso 1 1 calc R U . . .
H9B H 0.520014 0.317666 1.226367 0.023 Uiso 1 1 calc R U . . .
C10 C 0.30737(15) 0.39853(6) 1.13479(7) 0.02407(14) Uani 1 1 d . . . . .
H10C H 0.194087 0.380813 1.173016 0.029 Uiso 1 1 calc R U . . .
H10D H 0.371031 0.447505 1.176435 0.029 Uiso 1 1 calc R U . . .
C11 C 0.22391(15) 0.41950(8) 1.00684(8) 0.0301(2) Uani 1 1 d . . . . .
H11C H 0.123100 0.464233 1.003059 0.036 Uiso 1 1 calc R U . . .
H11D H 0.152327 0.371343 0.967047 0.036 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
O1A N1A 1.4523(7) . ?
O1A C1A 1.3412(8) . ?
O5A N3A 1.2305(9) . ?
O1 N1 1.4556(8) . ?
O1 C1 1.3455(8) . ?
O4A N3A 1.2269(8) . ?
O4 N3 1.2233(8) . ?
O5 N3 1.2324(9) . ?
O3A N2A 1.2305(8) . ?
O2A N2A 1.2228(9) . ?
O2 N2 1.2264(9) . ?
O3 N2 1.2283(8) . ?
N1A C7A 1.2791(8) . ?
N2A C2A 1.4654(8) . ?
N3A C4A 1.4584(9) . ?
N2 C2 1.4682(8) . ?
N3 C4 1.4598(9) . ?
N1 C7 1.2791(9) . ?
C2 C3 1.3905(9) . ?
C2 C1 1.4128(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.3829(9) . ?
C4A C5A 1.3914(8) . ?
C4A C3A 1.3802(9) . ?
C1A C2A 1.4118(8) . ?
C1A C6A 1.4061(9) . ?
C6 H6 0.9500 . ?
C6 C5 1.3815(9) . ?
C6 C1 1.4069(9) . ?
C4 C5 1.3902(9) . ?
C2A C3A 1.3881(9) . ?
C7A C12A 1.4992(10) . ?
C7A C8A 1.5011(9) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3804(9) . ?
C3A H3A 0.9500 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C8A 1.5356(10) . ?
C9A C10A 1.5288(11) . ?
C5 H5 0.9500 . ?
C6A H6A 0.9500 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C12A C11A 1.5349(12) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C10A 1.5258(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5002(9) . ?
C8 C9 1.5337(11) . ?
C7 C12 1.4971(11) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C11 1.5385(15) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5266(12) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 C11 1.5226(13) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?

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
C1A O1A N1A 111.98(5) . . ?
C1 O1 N1 111.93(5) . . ?
C7A N1A O1A 109.62(5) . . ?
O3A N2A C2A 117.36(6) . . ?
O2A N2A O3A 123.36(6) . . ?
O2A N2A C2A 119.28(6) . . ?
O5A N3A C4A 118.13(6) . . ?
O4A N3A O5A 123.75(6) . . ?
O4A N3A C4A 118.11(6) . . ?
O2 N2 O3 123.70(6) . . ?
O2 N2 C2 118.99(6) . . ?
O3 N2 C2 117.31(6) . . ?
O4 N3 O5 123.89(6) . . ?
O4 N3 C4 118.20(6) . . ?
O5 N3 C4 117.91(6) . . ?
C7 N1 O1 109.73(6) . . ?
C3 C2 N2 116.07(5) . . ?
C3 C2 C1 121.44(6) . . ?
C1 C2 N2 122.48(6) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.55(6) . . ?
C4 C3 H3 120.7 . . ?
C5A C4A N3A 119.67(6) . . ?
C3A C4A N3A 118.92(5) . . ?
C3A C4A C5A 121.41(6) . . ?
O1A C1A C2A 119.00(6) . . ?
O1A C1A C6A 123.00(5) . . ?
C6A C1A C2A 117.99(6) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C1 120.75(6) . . ?
C1 C6 H6 119.6 . . ?
C3 C4 N3 118.82(6) . . ?
C3 C4 C5 121.61(6) . . ?
C5 C4 N3 119.57(6) . . ?
C1A C2A N2A 122.68(6) . . ?
C3A C2A N2A 116.22(5) . . ?
C3A C2A C1A 121.09(6) . . ?
N1A C7A C12A 127.39(6) . . ?
N1A C7A C8A 115.16(6) . . ?
C12A C7A C8A 117.43(6) . . ?
C4A C5A H5A 120.3 . . ?
C6A C5A C4A 119.45(6) . . ?
C6A C5A H5A 120.3 . . ?
C4A C3A C2A 119.01(6) . . ?
C4A C3A H3A 120.5 . . ?
C2A C3A H3A 120.5 . . ?
H9AA C9A H9AB 108.1 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C10A C9A H9AA 109.5 . . ?
C10A C9A H9AB 109.5 . . ?
C10A C9A C8A 110.80(6) . . ?
C6 C5 C4 119.64(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A C1A 120.91(6) . . ?
C5A C6A H6A 119.5 . . ?
C7A C12A H12A 109.4 . . ?
C7A C12A H12B 109.4 . . ?
C7A C12A C11A 111.12(6) . . ?
H12A C12A H12B 108.0 . . ?
C11A C12A H12A 109.4 . . ?
C11A C12A H12B 109.4 . . ?
C12A C11A H11A 109.2 . . ?
C12A C11A H11B 109.2 . . ?
H11A C11A H11B 107.9 . . ?
C10A C11A C12A 111.84(7) . . ?
C10A C11A H11A 109.2 . . ?
C10A C11A H11B 109.2 . . ?
O1 C1 C2 119.16(6) . . ?
O1 C1 C6 122.86(6) . . ?
C6 C1 C2 117.96(6) . . ?
H8A C8 H8B 108.0 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 C9 111.06(6) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N1 C7 C8 115.33(6) . . ?
N1 C7 C12 127.61(6) . . ?
C12 C7 C8 117.06(6) . . ?
C7A C8A C9A 111.66(6) . . ?
C7A C8A H8AA 109.3 . . ?
C7A C8A H8AB 109.3 . . ?
C9A C8A H8AA 109.3 . . ?
C9A C8A H8AB 109.3 . . ?
H8AA C8A H8AB 107.9 . . ?
C7 C12 H12C 109.5 . . ?
C7 C12 H12D 109.5 . . ?
C7 C12 C11 110.51(7) . . ?
H12C C12 H12D 108.1 . . ?
C11 C12 H12C 109.5 . . ?
C11 C12 H12D 109.5 . . ?
C9A C10A H10A 109.7 . . ?
C9A C10A H10B 109.7 . . ?
C11A C10A C9A 109.98(6) . . ?
C11A C10A H10A 109.7 . . ?
C11A C10A H10B 109.7 . . ?
H10A C10A H10B 108.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 C8 110.61(7) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10C 109.6 . . ?
C9 C10 H10D 109.6 . . ?
H10C C10 H10D 108.1 . . ?
C11 C10 C9 110.15(7) . . ?
C11 C10 H10C 109.6 . . ?
C11 C10 H10D 109.6 . . ?
C12 C11 H11C 109.2 . . ?
C12 C11 H11D 109.2 . . ?
C10 C11 C12 112.05(8) . . ?
C10 C11 H11C 109.2 . . ?
C10 C11 H11D 109.2 . . ?
H11C C11 H11D 107.9 . . ?

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
O1A N1A C7A C12A -0.21(10) . . . . ?
O1A N1A C7A C8A 178.10(6) . . . . ?
O1A C1A C2A N2A -5.19(10) . . . . ?
O1A C1A C2A C3A 176.09(6) . . . . ?
O1A C1A C6A C5A -177.36(7) . . . . ?
O5A N3A C4A C5A -0.59(10) . . . . ?
O5A N3A C4A C3A 179.32(7) . . . . ?
O1 N1 C7 C8 179.94(6) . . . . ?
O1 N1 C7 C12 -0.74(12) . . . . ?
O4A N3A C4A C5A -179.74(7) . . . . ?
O4A N3A C4A C3A 0.17(10) . . . . ?
O4 N3 C4 C3 -0.24(10) . . . . ?
O4 N3 C4 C5 179.75(7) . . . . ?
O5 N3 C4 C3 -179.43(7) . . . . ?
O5 N3 C4 C5 0.56(10) . . . . ?
O3A N2A C2A C1A 179.32(7) . . . . ?
O3A N2A C2A C3A -1.90(10) . . . . ?
O2A N2A C2A C1A -0.22(10) . . . . ?
O2A N2A C2A C3A 178.56(7) . . . . ?
O2 N2 C2 C3 -179.34(7) . . . . ?
O2 N2 C2 C1 -0.68(10) . . . . ?
O3 N2 C2 C3 1.07(10) . . . . ?
O3 N2 C2 C1 179.73(7) . . . . ?
N1A O1A C1A C2A -179.00(5) . . . . ?
N1A O1A C1A C6A 0.93(9) . . . . ?
N1A C7A C12A C11A -135.48(8) . . . . ?
N1A C7A C8A C9A 134.47(7) . . . . ?
N2A C2A C3A C4A -177.09(6) . . . . ?
N3A C4A C5A C6A 176.85(6) . . . . ?
N3A C4A C3A C2A -178.11(6) . . . . ?
N2 C2 C3 C4 178.44(6) . . . . ?
N2 C2 C1 O1 2.26(10) . . . . ?
N2 C2 C1 C6 -176.67(6) . . . . ?
N3 C4 C5 C6 -177.83(6) . . . . ?
N1 O1 C1 C2 177.25(6) . . . . ?
N1 O1 C1 C6 -3.88(10) . . . . ?
N1 C7 C12 C11 132.62(9) . . . . ?
C2 C3 C4 N3 178.15(6) . . . . ?
C2 C3 C4 C5 -1.84(10) . . . . ?
C3 C2 C1 O1 -179.15(6) . . . . ?
C3 C2 C1 C6 1.93(10) . . . . ?
C3 C4 C5 C6 2.16(11) . . . . ?
C4A C5A C6A C1A 0.79(11) . . . . ?
C1A O1A N1A C7A -166.67(6) . . . . ?
C1A C2A C3A C4A 1.71(10) . . . . ?
C2A C1A C6A C5A 2.56(10) . . . . ?
C7A C12A C11A C10A -51.17(9) . . . . ?
C5A C4A C3A C2A 1.80(10) . . . . ?
C3A C4A C5A C6A -3.06(11) . . . . ?
C5 C6 C1 O1 179.51(7) . . . . ?
C5 C6 C1 C2 -1.61(10) . . . . ?
C6A C1A C2A N2A 174.88(6) . . . . ?
C6A C1A C2A C3A -3.84(10) . . . . ?
C12A C7A C8A C9A -47.04(9) . . . . ?
C12A C11A C10A C9A 58.73(9) . . . . ?
C1 O1 N1 C7 164.53(6) . . . . ?
C1 C2 C3 C4 -0.24(10) . . . . ?
C1 C6 C5 C4 -0.37(11) . . . . ?
C8 C7 C12 C11 -48.07(11) . . . . ?
C8 C9 C10 C11 58.62(10) . . . . ?
C7 C8 C9 C10 -53.34(9) . . . . ?
C7 C12 C11 C10 51.30(11) . . . . ?
C8A C7A C12A C11A 46.24(9) . . . . ?
C8A C9A C10A C11A -58.71(9) . . . . ?
C10A C9A C8A C7A 51.95(8) . . . . ?
C9 C8 C7 N1 -130.95(7) . . . . ?
C9 C8 C7 C12 49.66(10) . . . . ?
C9 C10 C11 C12 -58.04(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.369
_oxdiff_exptl_absorpt_empirical_full_min 0.759
