# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_DMAT-B
_database_code_depnum_ccdc_archive 'CCDC 2118365'
loop_
_audit_author_name
_audit_author_address
'Baolei Tang'
;JiLin University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-01-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.7988(3)
_cell_length_b                   17.3121(13)
_cell_length_c                   11.8745(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.415(3)
_cell_angle_gamma                90
_cell_volume                     986.20(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5114
_cell_measurement_temperature    273.0
_cell_measurement_theta_max      26.7185
_cell_measurement_theta_min      2.9095
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19245
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.766
_diffrn_reflns_theta_min         2.912
_diffrn_ambient_temperature      273.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1210
_reflns_number_total             2090
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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         0.295
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²+0.5876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1668
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00C(H00C)
2.c Idealised Me refined as rotating group:
 C00E(H00B,H00D,H00E), C00F(H00F,H00G,H00H)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.7498(4) 0.67020(11) 0.43217(15) 0.0561(5) Uani 1 1 d . . . . .
O002 O -0.2076(4) 0.39114(12) 0.30506(16) 0.0604(6) Uani 1 1 d . . . . .
O003 O 0.8438(4) 0.69593(12) 0.25223(16) 0.0593(6) Uani 1 1 d . . . . .
O004 O -0.1822(5) 0.41092(13) 0.12083(17) 0.0743(7) Uani 1 1 d . . . . .
C005 C 0.0994(5) 0.48783(14) 0.2457(2) 0.0425(6) Uani 1 1 d . . . . .
N1 N 0.5319(6) 0.62315(17) 0.0914(2) 0.0751(8) Uani 1 1 d . . . . .
H1A H 0.422413 0.620149 0.032800 0.090 Uiso 1 1 d R U . . .
H1B H 0.553381 0.671097 0.109362 0.090 Uiso 1 1 d R U . . .
C007 C 0.5008(5) 0.59992(14) 0.2937(2) 0.0426(6) Uani 1 1 d . . . . .
C008 C 0.7139(5) 0.65900(15) 0.3205(2) 0.0464(6) Uani 1 1 d . . . . .
C009 C 0.1821(5) 0.50190(15) 0.3576(2) 0.0473(6) Uani 1 1 d . . . . .
H009 H 0.105248 0.473897 0.415997 0.057 Uiso 1 1 calc R U . . .
C00A C 0.3788(5) 0.55777(15) 0.3796(2) 0.0461(6) Uani 1 1 d . . . . .
H00A H 0.432408 0.567824 0.453916 0.055 Uiso 1 1 calc R U . . .
C00B C -0.1096(6) 0.42723(15) 0.2154(2) 0.0489(7) Uani 1 1 d . . . . .
C00C C 0.2167(6) 0.52851(15) 0.1598(2) 0.0489(7) Uani 1 1 d . . . . .
H00C H 0.160676 0.518017 0.085812 0.059 Uiso 1 1 calc R U . . .
C00D C 0.4187(6) 0.58539(16) 0.1806(2) 0.0479(6) Uani 1 1 d . . . . .
C00E C 0.9574(7) 0.72655(18) 0.4657(3) 0.0628(8) Uani 1 1 d . . . . .
H00B H 0.911536 0.775540 0.432216 0.094 Uiso 1 1 calc R U . . .
H00D H 1.136855 0.710106 0.440975 0.094 Uiso 1 1 calc R U . . .
H00E H 0.961815 0.731490 0.546263 0.094 Uiso 1 1 calc R U . . .
C00F C -0.4050(7) 0.32969(18) 0.2842(3) 0.0654(9) Uani 1 1 d . . . . .
H00F H -0.535840 0.345129 0.226054 0.098 Uiso 1 1 calc R U . . .
H00G H -0.502674 0.318810 0.351993 0.098 Uiso 1 1 calc R U . . .
H00H H -0.307788 0.284203 0.260747 0.098 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0573(12) 0.0615(12) 0.0492(11) -0.0039(9) -0.0002(8) -0.0124(9)
O002 0.0602(13) 0.0648(13) 0.0562(11) -0.0022(9) 0.0014(9) -0.0176(10)
O003 0.0594(13) 0.0618(12) 0.0566(12) 0.0077(9) 0.0032(9) -0.0110(10)
O004 0.0924(18) 0.0778(15) 0.0519(12) -0.0034(11) -0.0124(11) -0.0230(12)
C005 0.0374(14) 0.0449(14) 0.0452(14) -0.0023(11) -0.0014(10) 0.0044(11)
N1 0.092(2) 0.085(2) 0.0473(14) 0.0081(13) -0.0038(13) -0.0283(16)
C007 0.0397(14) 0.0448(14) 0.0434(13) 0.0015(11) 0.0010(10) 0.0039(11)
C008 0.0427(15) 0.0483(14) 0.0482(15) 0.0023(12) -0.0024(11) 0.0080(12)
C009 0.0517(16) 0.0495(15) 0.0409(14) 0.0005(11) 0.0030(11) -0.0030(13)
C00A 0.0484(16) 0.0505(15) 0.0393(13) -0.0002(11) -0.0017(11) 0.0014(12)
C00B 0.0508(16) 0.0471(15) 0.0487(15) -0.0017(12) 0.0004(12) 0.0034(12)
C00C 0.0532(17) 0.0535(16) 0.0398(13) -0.0006(11) -0.0024(11) -0.0015(13)
C00D 0.0489(16) 0.0522(15) 0.0426(13) 0.0040(12) 0.0020(11) 0.0006(12)
C00E 0.0614(19) 0.0623(18) 0.0646(18) -0.0119(14) -0.0018(14) -0.0115(15)
C00F 0.0581(19) 0.0617(19) 0.076(2) -0.0046(15) -0.0008(15) -0.0159(15)

_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
O001 C008 1.347(3) . ?
O001 C00E 1.443(3) . ?
O002 C00B 1.330(3) . ?
O002 C00F 1.442(3) . ?
O003 C008 1.216(3) . ?
O004 C00B 1.202(3) . ?
C005 C009 1.399(3) . ?
C005 C00B 1.489(4) . ?
C005 C00C 1.372(4) . ?
N1 H1A 0.8633 . ?
N1 H1B 0.8625 . ?
N1 C00D 1.369(3) . ?
C007 C008 1.475(4) . ?
C007 C00A 1.394(3) . ?
C007 C00D 1.412(3) . ?
C009 H009 0.9300 . ?
C009 C00A 1.372(4) . ?
C00A H00A 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00D 1.400(4) . ?
C00E H00B 0.9600 . ?
C00E H00D 0.9600 . ?
C00E H00E 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 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
C008 O001 C00E 116.1(2) . . ?
C00B O002 C00F 116.9(2) . . ?
C009 C005 C00B 121.7(2) . . ?
C00C C005 C009 120.3(2) . . ?
C00C C005 C00B 117.9(2) . . ?
H1A N1 H1B 108.9 . . ?
C00D N1 H1A 110.5 . . ?
C00D N1 H1B 108.4 . . ?
C00A C007 C008 120.4(2) . . ?
C00A C007 C00D 119.3(2) . . ?
C00D C007 C008 120.3(2) . . ?
O001 C008 C007 112.6(2) . . ?
O003 C008 O001 121.7(2) . . ?
O003 C008 C007 125.7(2) . . ?
C005 C009 H009 120.6 . . ?
C00A C009 C005 118.8(2) . . ?
C00A C009 H009 120.6 . . ?
C007 C00A H00A 119.0 . . ?
C009 C00A C007 121.9(2) . . ?
C009 C00A H00A 119.0 . . ?
O002 C00B C005 112.8(2) . . ?
O004 C00B O002 122.5(3) . . ?
O004 C00B C005 124.7(3) . . ?
C005 C00C H00C 119.2 . . ?
C005 C00C C00D 121.6(2) . . ?
C00D C00C H00C 119.2 . . ?
N1 C00D C007 123.0(3) . . ?
N1 C00D C00C 119.0(2) . . ?
C00C C00D C007 118.0(2) . . ?
O001 C00E H00B 109.5 . . ?
O001 C00E H00D 109.5 . . ?
O001 C00E H00E 109.5 . . ?
H00B C00E H00D 109.5 . . ?
H00B C00E H00E 109.5 . . ?
H00D C00E H00E 109.5 . . ?
O002 C00F H00F 109.5 . . ?
O002 C00F H00G 109.5 . . ?
O002 C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 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
C005 C009 C00A C007 -0.9(4) . . . . ?
C005 C00C C00D N1 178.9(3) . . . . ?
C005 C00C C00D C007 0.2(4) . . . . ?
C008 C007 C00A C009 -179.3(2) . . . . ?
C008 C007 C00D N1 1.1(4) . . . . ?
C008 C007 C00D C00C 179.7(2) . . . . ?
C009 C005 C00B O002 1.5(4) . . . . ?
C009 C005 C00B O004 -177.6(3) . . . . ?
C009 C005 C00C C00D -0.7(4) . . . . ?
C00A C007 C008 O001 -5.6(3) . . . . ?
C00A C007 C008 O003 175.8(3) . . . . ?
C00A C007 C00D N1 -178.7(3) . . . . ?
C00A C007 C00D C00C -0.2(4) . . . . ?
C00B C005 C009 C00A 179.0(2) . . . . ?
C00B C005 C00C C00D -178.7(2) . . . . ?
C00C C005 C009 C00A 1.0(4) . . . . ?
C00C C005 C00B O002 179.5(2) . . . . ?
C00C C005 C00B O004 0.5(4) . . . . ?
C00D C007 C008 O001 174.6(2) . . . . ?
C00D C007 C008 O003 -4.1(4) . . . . ?
C00D C007 C00A C009 0.5(4) . . . . ?
C00E O001 C008 O003 -2.0(4) . . . . ?
C00E O001 C008 C007 179.3(2) . . . . ?
C00F O002 C00B O004 0.9(4) . . . . ?
C00F O002 C00B C005 -178.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_DMAT-G
_database_code_depnum_ccdc_archive 'CCDC 2118366'
loop_
_audit_author_name
_audit_author_address
'Baolei Tang'
;JiLin University
China
;
_audit_update_record             
;
2021-10-28 deposited with the CCDC.	2022-01-28 downloaded from the CCDC.
;
_audit_creation_date             2020-08-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        DMAT-G
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H12 N O4'
_chemical_formula_weight         210.21
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   22.016(9)
_cell_length_b                   3.9336(15)
_cell_length_c                   11.301(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     978.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5117
_cell_measurement_temperature    273.0
_cell_measurement_theta_max      26.736
_cell_measurement_theta_min      2.583
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14643
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.736
_diffrn_reflns_theta_min         2.583
_diffrn_ambient_temperature      273.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                1625
_reflns_number_total             2054
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.175
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.070
_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)+(0.0595P)²+0.1730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00D(H00D)
2.c Idealised Me refined as rotating group:
 C00E(H00b,H00c,H00e), C00F(H00f,H00g,H00h)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.41156(11) -0.0074(7) 0.4076(2) 0.0533(7) Uani 1 1 d . . . . .
O7 O 0.69133(11) 0.6597(7) 0.6492(2) 0.0548(7) Uani 1 1 d . . . . .
O003 O 0.39492(12) 0.1159(8) 0.5968(2) 0.0645(8) Uani 1 1 d . . . . .
O004 O 0.71618(13) 0.4996(9) 0.4664(3) 0.0677(8) Uani 1 1 d . . . . .
C005 C 0.49269(14) 0.2256(8) 0.5163(3) 0.0370(7) Uani 1 1 d . . . . .
N2 N 0.62917(16) 0.2089(11) 0.3340(3) 0.0668(10) Uani 1 1 d . . . . .
H2A H 0.664326 0.144540 0.359538 0.080 Uiso 1 1 d R U . . .
H2B H 0.614202 0.048960 0.290419 0.080 Uiso 1 1 d R U . . .
C007 C 0.51324(15) 0.3896(8) 0.6183(3) 0.0422(8) Uani 1 1 d . . . . .
H007 H 0.486851 0.430500 0.680921 0.051 Uiso 1 1 calc R U . . .
C008 C 0.42870(15) 0.1084(8) 0.5132(3) 0.0409(7) Uani 1 1 d . . . . .
C009 C 0.61350(15) 0.4307(8) 0.5316(3) 0.0384(7) Uani 1 1 d . . . . .
C00A C 0.57272(15) 0.4894(9) 0.6249(3) 0.0407(8) Uani 1 1 d . . . . .
H00A H 0.586429 0.598610 0.692820 0.049 Uiso 1 1 calc R U . . .
C00B C 0.67770(16) 0.5319(9) 0.5425(3) 0.0442(8) Uani 1 1 d . . . . .
C00C C 0.59266(15) 0.2697(9) 0.4277(3) 0.0414(8) Uani 1 1 d . . . . .
C00D C 0.53139(15) 0.1681(8) 0.4226(3) 0.0398(7) Uani 1 1 d . . . . .
H00D H 0.516835 0.060709 0.354991 0.048 Uiso 1 1 calc R U . . .
C00E C 0.75348(19) 0.7598(12) 0.6665(4) 0.0617(11) Uani 1 1 d . . . . .
H00B H 0.762749 0.948699 0.615863 0.093 Uiso 1 1 calc R U . . .
H00C H 0.779748 0.572639 0.647681 0.093 Uiso 1 1 calc R U . . .
H00E H 0.759467 0.824844 0.747560 0.093 Uiso 1 1 calc R U . . .
C00F C 0.34981(17) -0.1332(11) 0.3997(4) 0.0602(11) Uani 1 1 d . . . . .
H00F H 0.342957 -0.225526 0.322153 0.090 Uiso 1 1 calc R U . . .
H00G H 0.321919 0.050026 0.413611 0.090 Uiso 1 1 calc R U . . .
H00H H 0.343666 -0.307498 0.457901 0.090 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0408(13) 0.0719(17) 0.0473(14) -0.0087(14) -0.0002(12) -0.0098(12)
O7 0.0412(14) 0.0726(18) 0.0506(15) -0.0046(13) -0.0034(11) -0.0098(13)
O003 0.0440(14) 0.103(2) 0.0463(16) 0.0006(16) 0.0053(13) -0.0078(14)
O004 0.0449(16) 0.104(2) 0.0546(16) -0.0076(15) 0.0064(13) -0.0059(16)
C005 0.0351(17) 0.0398(16) 0.0362(15) 0.0051(15) -0.0020(13) 0.0029(13)
N2 0.051(2) 0.101(3) 0.0484(19) -0.0177(19) 0.0083(15) -0.0046(19)
C007 0.0404(17) 0.0472(19) 0.0390(17) -0.0011(16) 0.0030(14) 0.0029(15)
C008 0.0406(18) 0.0425(18) 0.0396(17) 0.0056(15) -0.0014(15) 0.0018(14)
C009 0.0380(17) 0.0403(16) 0.0370(17) 0.0035(15) -0.0028(13) 0.0032(13)
C00A 0.0433(18) 0.0450(19) 0.0338(17) -0.0019(15) -0.0027(14) 0.0021(13)
C00B 0.0400(19) 0.051(2) 0.0418(18) 0.0044(16) -0.0025(15) 0.0001(15)
C00C 0.0408(18) 0.0463(19) 0.0370(17) 0.0038(15) 0.0021(15) 0.0047(14)
C00D 0.0411(18) 0.0434(18) 0.0350(16) 0.0011(15) -0.0018(14) 0.0000(13)
C00E 0.043(2) 0.075(3) 0.066(3) 0.000(2) -0.0091(18) -0.014(2)
C00F 0.042(2) 0.071(3) 0.068(3) -0.011(2) -0.0065(19) -0.0060(17)

_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
O001 C008 1.331(4) . ?
O001 C00F 1.450(4) . ?
O7 C00B 1.341(4) . ?
O7 C00E 1.437(5) . ?
O003 C008 1.203(5) . ?
O004 C00B 1.214(4) . ?
C005 C007 1.396(5) . ?
C005 C008 1.483(5) . ?
C005 C00D 1.378(4) . ?
N2 H2A 0.8640 . ?
N2 H2B 0.8642 . ?
N2 C00C 1.351(4) . ?
C007 H007 0.9300 . ?
C007 C00A 1.369(5) . ?
C009 C00A 1.404(5) . ?
C009 C00B 1.473(5) . ?
C009 C00C 1.411(5) . ?
C00A H00A 0.9300 . ?
C00C C00D 1.408(5) . ?
C00D H00D 0.9300 . ?
C00E H00B 0.9600 . ?
C00E H00C 0.9600 . ?
C00E H00E 0.9600 . ?
C00F H00F 0.9600 . ?
C00F H00G 0.9600 . ?
C00F H00H 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
C008 O001 C00F 116.0(3) . . ?
C00B O7 C00E 116.0(3) . . ?
C007 C005 C008 118.1(3) . . ?
C00D C005 C007 120.7(3) . . ?
C00D C005 C008 121.2(3) . . ?
H2A N2 H2B 108.6 . . ?
C00C N2 H2A 108.8 . . ?
C00C N2 H2B 110.4 . . ?
C005 C007 H007 120.4 . . ?
C00A C007 C005 119.2(3) . . ?
C00A C007 H007 120.4 . . ?
O001 C008 C005 113.4(3) . . ?
O003 C008 O001 122.5(3) . . ?
O003 C008 C005 124.1(3) . . ?
C00A C009 C00B 120.4(3) . . ?
C00A C009 C00C 119.4(3) . . ?
C00C C009 C00B 120.2(3) . . ?
C007 C00A C009 121.6(3) . . ?
C007 C00A H00A 119.2 . . ?
C009 C00A H00A 119.2 . . ?
O7 C00B C009 113.0(3) . . ?
O004 C00B O7 121.4(3) . . ?
O004 C00B C009 125.6(3) . . ?
N2 C00C C009 122.6(3) . . ?
N2 C00C C00D 119.2(3) . . ?
C00D C00C C009 118.2(3) . . ?
C005 C00D C00C 120.9(3) . . ?
C005 C00D H00D 119.5 . . ?
C00C C00D H00D 119.5 . . ?
O7 C00E H00B 109.5 . . ?
O7 C00E H00C 109.5 . . ?
O7 C00E H00E 109.5 . . ?
H00B C00E H00C 109.5 . . ?
H00B C00E H00E 109.5 . . ?
H00C C00E H00E 109.5 . . ?
O001 C00F H00F 109.5 . . ?
O001 C00F H00G 109.5 . . ?
O001 C00F H00H 109.5 . . ?
H00F C00F H00G 109.5 . . ?
H00F C00F H00H 109.5 . . ?
H00G C00F H00H 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
C005 C007 C00A C009 0.0(5) . . . . ?
N2 C00C C00D C005 -180.0(4) . . . . ?
C007 C005 C008 O001 172.4(3) . . . . ?
C007 C005 C008 O003 -7.5(5) . . . . ?
C007 C005 C00D C00C 0.7(5) . . . . ?
C008 C005 C007 C00A 177.7(3) . . . . ?
C008 C005 C00D C00C -177.8(3) . . . . ?
C009 C00C C00D C005 0.3(5) . . . . ?
C00A C009 C00B O7 3.6(4) . . . . ?
C00A C009 C00B O004 -178.3(4) . . . . ?
C00A C009 C00C N2 179.2(4) . . . . ?
C00A C009 C00C C00D -1.1(4) . . . . ?
C00B C009 C00A C007 -178.2(3) . . . . ?
C00B C009 C00C N2 -1.7(5) . . . . ?
C00B C009 C00C C00D 178.1(3) . . . . ?
C00C C009 C00A C007 1.0(5) . . . . ?
C00C C009 C00B O7 -175.6(3) . . . . ?
C00C C009 C00B O004 2.6(5) . . . . ?
C00D C005 C007 C00A -0.8(5) . . . . ?
C00D C005 C008 O001 -9.1(4) . . . . ?
C00D C005 C008 O003 171.1(4) . . . . ?
C00E O7 C00B O004 1.0(5) . . . . ?
C00E O7 C00B C009 179.2(3) . . . . ?
C00F O001 C008 O003 -1.5(5) . . . . ?
C00F O001 C008 C005 178.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

