# 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_MPT-2-rt
_audit_block_doi                 10.5517/ccdc.csd.cc2c8g04
_database_code_depnum_ccdc_archive 'CCDC 2182865'
loop_
_audit_author_name
_audit_author_address
'Zaiyong Zhang'
;BIT
China
;
_audit_update_record             
;
2022-08-24 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N10 O6'
_chemical_formula_sum            'C6 H6 N10 O6'
_chemical_formula_weight         314.21
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1738(8)
_cell_length_b                   8.3136(10)
_cell_length_c                   19.948(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.253(4)
_cell_angle_gamma                90
_cell_volume                     1184.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.834
_cell_measurement_theta_min      3.117
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1055 before and 0.0582 after correction. The Ratio of minimum to maximum transmission is 0.8450. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8693
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.050
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1323
_reflns_number_total             2689
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2689
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.0704
_refine_ls_restrained_S_all      1.068
_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)+(0.0749P)²+1.0663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1654
_refine_ls_wR_factor_ref         0.2094
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 N2-H2B = N2-H2A
 0.87 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.b X=CH2 refined with riding coordinates:
 N10(H10A,H10B)
;
_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
N4 N 0.4827(4) 0.3656(4) 0.20230(16) 0.0439(8) Uani 1 1 d . . . . .
N6 N 0.4431(5) 0.3836(4) 0.31889(17) 0.0486(9) Uani 1 1 d . . . . .
O3 O 0.1952(4) 0.6528(4) 0.07252(17) 0.0716(10) Uani 1 1 d . . . . .
N3 N 0.3607(4) 0.4587(4) 0.16708(17) 0.0477(9) Uani 1 1 d . . . . .
O2 O 0.9698(4) 0.3366(4) 0.18750(18) 0.0725(10) Uani 1 1 d . . . . .
N7 N 0.3004(5) 0.4620(5) 0.33934(17) 0.0509(9) Uani 1 1 d . . . . .
N5 N 0.8178(5) 0.2952(5) 0.2083(2) 0.0555(10) Uani 1 1 d . . . . .
O1 O 0.8032(5) 0.1881(5) 0.24966(19) 0.0809(11) Uani 1 1 d . . . . .
O5 O 0.1057(5) 0.6520(5) 0.41675(18) 0.0781(11) Uani 1 1 d . . . . .
O6 O 0.3653(5) 0.7403(5) 0.46834(18) 0.0775(10) Uani 1 1 d . . . . .
N8 N 0.6117(5) 0.4116(5) 0.35200(18) 0.0547(10) Uani 1 1 d . . . . .
N2 N 0.7828(5) 0.5331(5) 0.0891(2) 0.0594(11) Uani 1 1 d D . . . .
N9 N 0.2751(6) 0.6518(5) 0.4275(2) 0.0602(10) Uani 1 1 d . . . . .
N1 N 0.3642(5) 0.6349(5) 0.07436(19) 0.0596(10) Uani 1 1 d . . . . .
C3 C 0.6579(5) 0.3792(5) 0.17954(19) 0.0412(9) Uani 1 1 d . . . . .
N10 N 0.7048(5) 0.5821(5) 0.4435(2) 0.0703(12) Uani 1 1 d . . . . .
H10A H 0.819694 0.552585 0.443433 0.084 Uiso 1 1 calc R . . . .
H10B H 0.673653 0.651577 0.472369 0.084 Uiso 1 1 calc R . . . .
C1 C 0.4578(5) 0.5287(5) 0.1218(2) 0.0460(10) Uani 1 1 d . . . . .
C5 C 0.3820(5) 0.5463(5) 0.3902(2) 0.0458(10) Uani 1 1 d . . . . .
C2 C 0.6478(5) 0.4860(5) 0.12679(19) 0.0438(10) Uani 1 1 d . . . . .
C4 C 0.4189(6) 0.2841(5) 0.2601(2) 0.0486(11) Uani 1 1 d . . . . .
H4A H 0.287674 0.256593 0.251001 0.058 Uiso 1 1 calc R . . . .
H4B H 0.488910 0.185088 0.268184 0.058 Uiso 1 1 calc R . . . .
O4 O 0.4608(5) 0.7037(5) 0.0361(2) 0.1006(15) Uani 1 1 d . . . . .
C6 C 0.5752(6) 0.5203(6) 0.3987(2) 0.0505(11) Uani 1 1 d . . . . .
H2A H 0.746(6) 0.590(5) 0.0547(16) 0.065(15) Uiso 1 1 d D . . . .
H2B H 0.896(3) 0.507(5) 0.1029(19) 0.050(13) Uiso 1 1 d 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
N4 N3 1.321(4) . ?
N4 C3 1.380(5) . ?
N4 C4 1.447(5) . ?
N6 N7 1.310(4) . ?
N6 N8 1.345(5) . ?
N6 C4 1.432(5) . ?
O3 N1 1.218(4) . ?
N3 C1 1.324(5) . ?
O2 N5 1.249(4) . ?
N7 C5 1.325(5) . ?
N5 O1 1.225(5) . ?
N5 C3 1.418(5) . ?
O5 N9 1.214(5) . ?
O6 N9 1.236(5) . ?
N8 C6 1.341(6) . ?
N2 C2 1.338(5) . ?
N2 H2A 0.854(19) . ?
N2 H2B 0.860(19) . ?
N9 C5 1.419(6) . ?
N1 C1 1.419(5) . ?
N1 O4 1.219(5) . ?
C3 C2 1.374(5) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C6 1.331(5) . ?
C1 C2 1.403(5) . ?
C5 C6 1.398(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

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
N3 N4 C3 110.9(3) . . ?
N3 N4 C4 117.1(3) . . ?
C3 N4 C4 131.6(3) . . ?
N7 N6 N8 117.0(3) . . ?
N7 N6 C4 120.2(3) . . ?
N8 N6 C4 122.6(3) . . ?
N4 N3 C1 104.8(3) . . ?
N6 N7 C5 101.5(3) . . ?
O2 N5 C3 115.4(4) . . ?
O1 N5 O2 123.7(4) . . ?
O1 N5 C3 121.0(4) . . ?
C6 N8 N6 103.5(3) . . ?
C2 N2 H2A 115(3) . . ?
C2 N2 H2B 117(3) . . ?
H2A N2 H2B 128(4) . . ?
O5 N9 O6 124.8(4) . . ?
O5 N9 C5 119.2(4) . . ?
O6 N9 C5 115.9(4) . . ?
O3 N1 C1 120.3(4) . . ?
O3 N1 O4 123.0(4) . . ?
O4 N1 C1 116.6(4) . . ?
N4 C3 N5 123.7(4) . . ?
C2 C3 N4 108.6(3) . . ?
C2 C3 N5 127.7(4) . . ?
H10A N10 H10B 120.0 . . ?
C6 N10 H10A 120.0 . . ?
C6 N10 H10B 120.0 . . ?
N3 C1 N1 118.8(4) . . ?
N3 C1 C2 114.2(4) . . ?
C2 C1 N1 127.0(4) . . ?
N7 C5 N9 120.4(4) . . ?
N7 C5 C6 112.0(4) . . ?
C6 C5 N9 127.6(4) . . ?
N2 C2 C3 129.0(4) . . ?
N2 C2 C1 129.4(4) . . ?
C3 C2 C1 101.5(3) . . ?
N4 C4 H4A 109.4 . . ?
N4 C4 H4B 109.4 . . ?
N6 C4 N4 111.0(3) . . ?
N6 C4 H4A 109.4 . . ?
N6 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
N8 C6 C5 105.9(4) . . ?
N10 C6 N8 123.8(4) . . ?
N10 C6 C5 130.2(4) . . ?


_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_mo_2022430_0m
_database_code_depnum_ccdc_archive 'CCDC 2178121'
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N10 O6'
_chemical_formula_sum            'C6 H6 N10 O6'
_chemical_formula_weight         314.21
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.1538(11)
_cell_length_b                   8.2580(14)
_cell_length_c                   19.830(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.353(5)
_cell_angle_gamma                90
_cell_volume                     1166.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.352
_cell_measurement_theta_min      2.952
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0663 before and 0.0543 after correction. The Ratio of minimum to maximum transmission is 0.8047. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8551
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.452
_diffrn_reflns_theta_min         2.063
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1701
_reflns_number_total             2352
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2352
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.107
_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)+(0.0588P)²+2.6504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1668
_refine_ls_wR_factor_ref         0.1830
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 N9-H9B = N9-H9A
 0.87 with sigma of 0.02
3.a Rotating group:
 N9(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_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
N6 N -0.0161(4) 0.3597(4) 0.20212(15) 0.0295(7) Uani 1 1 d . . . . .
N7 N -0.1389(4) 0.4547(4) 0.16662(15) 0.0318(7) Uani 1 1 d . . . . .
C5 C 0.1495(5) 0.4813(5) 0.12571(18) 0.0294(8) Uani 1 1 d . . . . .
C6 C -0.0422(5) 0.5248(5) 0.12070(18) 0.0323(9) Uani 1 1 d . . . . .
C4 C 0.1603(5) 0.3723(5) 0.17951(18) 0.0281(8) Uani 1 1 d . . . . .
O6 O 0.4727(4) 0.3313(4) 0.18681(16) 0.0461(8) Uani 1 1 d . . . . .
N10 N 0.3205(5) 0.2888(4) 0.20772(17) 0.0366(8) Uani 1 1 d . . . . .
O5 O 0.3068(4) 0.1818(4) 0.24989(16) 0.0521(9) Uani 1 1 d . . . . .
O3 O -0.0368(5) 0.7014(5) 0.03454(17) 0.0630(11) Uani 1 1 d . . . . .
O4 O -0.3067(4) 0.6502(4) 0.07145(15) 0.0463(8) Uani 1 1 d . . . . .
N8 N -0.1357(5) 0.6319(5) 0.07289(17) 0.0399(9) Uani 1 1 d . . . . .
N4 N -0.0570(4) 0.3772(4) 0.31934(16) 0.0338(8) Uani 1 1 d . . . . .
N3 N 0.1136(5) 0.4063(4) 0.35283(17) 0.0372(8) Uani 1 1 d . . . . .
C3 C -0.0806(6) 0.2755(5) 0.26031(18) 0.0333(9) Uani 1 1 d . . . . .
H3A H -0.214674 0.246442 0.250719 0.040 Uiso 1 1 calc R . . . .
H3B H -0.007946 0.174330 0.268721 0.040 Uiso 1 1 calc R . . . .
N2 N 0.2063(5) 0.5801(5) 0.44457(18) 0.0465(10) Uani 1 1 d . . . . .
H2A H 0.324715 0.551184 0.444503 0.056 Uiso 1 1 calc R . . . .
H2B H 0.173424 0.651461 0.474213 0.056 Uiso 1 1 calc R . . . .
N5 N -0.2010(5) 0.4561(4) 0.33943(16) 0.0352(8) Uani 1 1 d . . . . .
C1 C -0.1200(5) 0.5434(5) 0.39067(19) 0.0334(9) Uani 1 1 d . . . . .
C2 C 0.0763(6) 0.5154(5) 0.39958(19) 0.0340(9) Uani 1 1 d . . . . .
O1 O -0.1368(5) 0.7407(4) 0.46819(16) 0.0517(8) Uani 1 1 d . . . . .
O2 O -0.3980(4) 0.6485(4) 0.41659(16) 0.0514(9) Uani 1 1 d . . . . .
N1 N -0.2269(5) 0.6502(5) 0.42759(17) 0.0401(9) Uani 1 1 d . . . . .
N9 N 0.2856(5) 0.5289(5) 0.08767(18) 0.0385(8) Uani 1 1 d D . . . .
H9A H 0.239653 0.601003 0.057953 0.046 Uiso 1 1 d DGR . . . .
H9B H 0.397(3) 0.501(5) 0.1015(18) 0.028(11) Uiso 1 1 d 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
N6 N7 1.329(4) . ?
N6 C4 1.382(5) . ?
N6 C3 1.458(5) . ?
N7 C6 1.327(5) . ?
C5 C6 1.412(5) . ?
C5 C4 1.392(5) . ?
C5 N9 1.345(5) . ?
C6 N8 1.418(5) . ?
C4 N10 1.408(5) . ?
O6 N10 1.251(4) . ?
N10 O5 1.227(4) . ?
O3 N8 1.228(4) . ?
O4 N8 1.230(4) . ?
N4 N3 1.356(4) . ?
N4 C3 1.438(5) . ?
N4 N5 1.312(5) . ?
N3 C2 1.337(5) . ?
N2 C2 1.339(5) . ?
N5 C1 1.334(5) . ?
C1 C2 1.418(5) . ?
C1 N1 1.415(5) . ?
O1 N1 1.235(5) . ?
O2 N1 1.223(4) . ?

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
N7 N6 C4 111.2(3) . . ?
N7 N6 C3 117.3(3) . . ?
C4 N6 C3 131.2(3) . . ?
C6 N7 N6 105.1(3) . . ?
C4 C5 C6 101.7(3) . . ?
N9 C5 C6 129.4(4) . . ?
N9 C5 C4 128.9(4) . . ?
N7 C6 C5 113.9(3) . . ?
N7 C6 N8 119.2(3) . . ?
C5 C6 N8 126.9(3) . . ?
N6 C4 C5 108.1(3) . . ?
N6 C4 N10 124.6(3) . . ?
C5 C4 N10 127.3(3) . . ?
O6 N10 C4 115.6(3) . . ?
O5 N10 C4 120.6(3) . . ?
O5 N10 O6 123.8(3) . . ?
O3 N8 C6 116.3(3) . . ?
O3 N8 O4 123.9(4) . . ?
O4 N8 C6 119.9(3) . . ?
N3 N4 C3 122.3(3) . . ?
N5 N4 N3 117.4(3) . . ?
N5 N4 C3 120.1(3) . . ?
C2 N3 N4 103.3(3) . . ?
N4 C3 N6 110.2(3) . . ?
N4 N5 C1 101.7(3) . . ?
N5 C1 C2 111.2(4) . . ?
N5 C1 N1 120.9(4) . . ?
N1 C1 C2 127.9(4) . . ?
N3 C2 C1 106.4(3) . . ?
N2 C2 N3 124.0(4) . . ?
N2 C2 C1 129.5(4) . . ?
O1 N1 C1 116.1(3) . . ?
O2 N1 C1 118.7(4) . . ?
O2 N1 O1 125.2(4) . . ?


_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_2022601298k_0m
_database_code_depnum_ccdc_archive 'CCDC 2194551'
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N10 O6'
_chemical_formula_sum            'C6 H6 N10 O6'
_chemical_formula_weight         314.21
_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           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                   6.2935(3)
_cell_length_b                   11.7191(5)
_cell_length_c                   15.8519(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1169.14(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3763
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.184
_cell_measurement_theta_min      2.570
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1250 before and 0.0653 after correction. The Ratio of minimum to maximum transmission is 0.7952. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.785
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9578
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.161
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2108
_reflns_number_total             2669
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 716 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0392
_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)+(0.0373P)²+0.1926P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0945
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B)
2.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B), N9(H9A,H9B)
;
_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
O2 O 1.1512(3) 0.3305(2) 0.61374(14) 0.0461(5) Uani 1 1 d . . . . .
N7 N 0.4953(3) 0.54580(19) 0.33500(14) 0.0326(5) Uani 1 1 d . . . . .
O3 O 0.0318(3) 0.5395(2) 0.21024(14) 0.0536(6) Uani 1 1 d . . . . .
O4 O 0.2873(4) 0.4161(2) 0.21471(15) 0.0557(6) Uani 1 1 d . . . . .
O1 O 0.8151(3) 0.3335(2) 0.64348(14) 0.0553(7) Uani 1 1 d . . . . .
N4 N 0.9647(4) 0.3479(2) 0.59426(15) 0.0356(5) Uani 1 1 d . . . . .
N1 N 0.7589(3) 0.4270(2) 0.39769(14) 0.0334(5) Uani 1 1 d . . . . .
N3 N 1.0675(4) 0.4008(2) 0.45331(15) 0.0380(6) Uani 1 1 d . . . . .
N10 N 0.2048(4) 0.5053(2) 0.23709(15) 0.0401(6) Uani 1 1 d . . . . .
N2 N 0.9761(3) 0.4267(2) 0.38323(15) 0.0415(6) Uani 1 1 d . . . . .
N6 N 0.5625(4) 0.6287(2) 0.38534(15) 0.0415(6) Uani 1 1 d . . . . .
C00C C 0.9163(4) 0.3832(2) 0.51243(17) 0.0308(6) Uani 1 1 d . . . . .
O5 O 0.3054(5) 0.8876(2) 0.4096(2) 0.0846(9) Uani 1 1 d . . . . .
N8 N 0.4401(6) 0.8136(3) 0.4251(2) 0.0624(8) Uani 1 1 d . . . . .
C00F C 0.3089(4) 0.5749(2) 0.29596(17) 0.0333(6) Uani 1 1 d . . . . .
N5 N 0.5238(3) 0.3932(2) 0.51217(17) 0.0446(6) Uani 1 1 d . . . . .
H5A H 0.413681 0.405752 0.481400 0.054 Uiso 1 1 calc R . . . .
H5B H 0.508818 0.375823 0.564548 0.054 Uiso 1 1 calc R . . . .
N9 N 0.0777(5) 0.7438(3) 0.30144(19) 0.0599(8) Uani 1 1 d . . . . .
H9A H -0.012223 0.716315 0.265992 0.072 Uiso 1 1 calc R . . . .
H9B H 0.057517 0.810356 0.322823 0.072 Uiso 1 1 calc R . . . .
C00I C 0.2483(5) 0.6832(3) 0.32323(18) 0.0390(7) Uani 1 1 d . . . . .
C00J C 0.7155(4) 0.4005(2) 0.47902(18) 0.0309(6) Uani 1 1 d . . . . .
C00K C 0.6161(5) 0.4394(3) 0.32808(18) 0.0397(7) Uani 1 1 d . . . . .
H00A H 0.518712 0.375286 0.326840 0.048 Uiso 1 1 calc R . . . .
H00B H 0.695994 0.439413 0.275763 0.048 Uiso 1 1 calc R . . . .
C00L C 0.4163(5) 0.7101(2) 0.37776(18) 0.0417(7) Uani 1 1 d . . . . .
O6 O 0.5851(6) 0.8237(3) 0.4746(2) 0.0949(11) 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
O2 N4 1.230(3) . ?
N7 N6 1.326(3) . ?
N7 C00F 1.370(3) . ?
N7 C00K 1.464(4) . ?
O3 N10 1.236(3) . ?
O4 N10 1.220(3) . ?
O1 N4 1.234(3) . ?
N4 C00C 1.395(4) . ?
N1 N2 1.386(3) . ?
N1 C00J 1.354(4) . ?
N1 C00K 1.431(3) . ?
N3 N2 1.287(3) . ?
N3 C00C 1.351(3) . ?
N10 C00F 1.402(4) . ?
N6 C00L 1.331(4) . ?
C00C C00J 1.385(4) . ?
O5 N8 1.237(4) . ?
N8 C00L 1.434(4) . ?
N8 O6 1.209(4) . ?
C00F C00I 1.394(4) . ?
N5 C00J 1.319(3) . ?
N9 C00I 1.333(4) . ?
C00I C00L 1.401(4) . ?

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
N6 N7 C00F 111.2(2) . . ?
N6 N7 C00K 120.2(2) . . ?
C00F N7 C00K 128.5(2) . . ?
O2 N4 O1 123.1(2) . . ?
O2 N4 C00C 119.4(2) . . ?
O1 N4 C00C 117.5(2) . . ?
N2 N1 C00K 119.5(2) . . ?
C00J N1 N2 110.9(2) . . ?
C00J N1 C00K 129.1(2) . . ?
N2 N3 C00C 108.6(2) . . ?
O3 N10 C00F 116.9(3) . . ?
O4 N10 O3 123.5(3) . . ?
O4 N10 C00F 119.6(2) . . ?
N3 N2 N1 107.4(2) . . ?
N7 N6 C00L 104.5(2) . . ?
N3 C00C N4 122.4(2) . . ?
N3 C00C C00J 110.8(2) . . ?
C00J C00C N4 126.7(2) . . ?
O5 N8 C00L 114.7(3) . . ?
O6 N8 O5 125.3(3) . . ?
O6 N8 C00L 120.1(3) . . ?
N7 C00F N10 123.8(3) . . ?
N7 C00F C00I 108.7(2) . . ?
C00I C00F N10 127.5(3) . . ?
C00F C00I C00L 100.9(2) . . ?
N9 C00I C00F 128.7(3) . . ?
N9 C00I C00L 130.4(3) . . ?
N1 C00J C00C 102.3(2) . . ?
N5 C00J N1 125.4(3) . . ?
N5 C00J C00C 132.3(3) . . ?
N1 C00K N7 110.8(2) . . ?
N6 C00L N8 119.1(3) . . ?
N6 C00L C00I 114.6(3) . . ?
C00I C00L N8 126.3(3) . . ?


_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_mo_2022593_0m
_database_code_depnum_ccdc_archive 'CCDC 2182866'
_audit_update_record             
;
2022-06-29 deposited with the CCDC.	2022-08-25 downloaded from the CCDC.
;
_audit_creation_date             2022-06-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H6 N10 O6'
_chemical_formula_sum            'C6 H6 N10 O6'
_chemical_formula_weight         314.21
_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           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                   6.2740(4)
_cell_length_b                   11.6263(7)
_cell_length_c                   15.6940(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1144.77(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3585
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.672
_cell_measurement_theta_min      2.180
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7008
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0869 before and 0.0725 after correction. The Ratio of minimum to maximum transmission is 0.9399. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14243
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.180
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2018
_reflns_number_total             2626
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 688 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2626
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.075
_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)+(0.0399P)²+0.1393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0975
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00M(H00E,H00F)
2.b X=CH2 refined with riding coordinates:
 N00D(H00A,H00B), N00G(H00C,H00D)
;
_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
O001 O 0.1574(3) -0.6721(2) -0.38690(15) 0.0260(6) Uani 1 1 d . . . . .
O002 O -0.9699(4) -0.4610(2) -0.79303(16) 0.0308(6) Uani 1 1 d . . . . .
O003 O -0.7072(4) -0.5837(2) -0.79116(16) 0.0320(6) Uani 1 1 d . . . . .
O004 O -0.1820(4) -0.6674(2) -0.35621(15) 0.0316(6) Uani 1 1 d . . . . .
N005 N -0.5036(4) -0.4537(2) -0.66715(17) 0.0204(6) Uani 1 1 d . . . . .
N006 N -0.7933(5) -0.4937(3) -0.76682(17) 0.0244(7) Uani 1 1 d . . . . .
N007 N -0.0308(4) -0.6535(2) -0.40635(17) 0.0219(6) Uani 1 1 d . . . . .
N008 N 0.0733(4) -0.5994(3) -0.54871(17) 0.0229(7) Uani 1 1 d . . . . .
N009 N -0.2365(4) -0.5726(2) -0.60488(16) 0.0207(6) Uani 1 1 d . . . . .
O00A O -0.7027(5) -0.1114(2) -0.58856(19) 0.0457(8) Uani 1 1 d . . . . .
N00B N -0.0185(4) -0.5730(3) -0.61971(17) 0.0245(7) Uani 1 1 d . . . . .
N00C N -0.4390(5) -0.3708(2) -0.61485(18) 0.0249(7) Uani 1 1 d . . . . .
N00D N -0.4732(4) -0.6075(3) -0.48921(18) 0.0249(7) Uani 1 1 d . . . . .
H00A H -0.586465 -0.594857 -0.520896 0.030 Uiso 1 1 calc R . . . .
H00B H -0.488010 -0.625555 -0.435071 0.030 Uiso 1 1 calc R . . . .
O00E O -0.4239(5) -0.1763(2) -0.52083(18) 0.0499(8) Uani 1 1 d . . . . .
N00F N -0.5681(6) -0.1863(3) -0.57293(19) 0.0349(8) Uani 1 1 d . . . . .
N00G N -0.9282(5) -0.2563(3) -0.6991(2) 0.0331(8) Uani 1 1 d . . . . .
H00C H -1.019549 -0.284508 -0.736181 0.040 Uiso 1 1 calc R . . . .
H00D H -0.950889 -0.188293 -0.676194 0.040 Uiso 1 1 calc R . . . .
C00H C -0.0788(5) -0.6169(3) -0.4889(2) 0.0197(7) Uani 1 1 d . . . . .
C00I C -0.2812(5) -0.5995(3) -0.5228(2) 0.0193(7) Uani 1 1 d . . . . .
C00J C -0.6922(5) -0.4248(3) -0.7067(2) 0.0201(7) Uani 1 1 d . . . . .
C00K C -0.5875(6) -0.2894(3) -0.6216(2) 0.0247(8) Uani 1 1 d . . . . .
C00L C -0.7548(6) -0.3168(3) -0.6776(2) 0.0235(8) Uani 1 1 d . . . . .
C00M C -0.3798(5) -0.5609(3) -0.6754(2) 0.0230(8) Uani 1 1 d . . . . .
H00E H -0.477946 -0.627519 -0.677123 0.028 Uiso 1 1 calc R . . . .
H00F H -0.297915 -0.559612 -0.729355 0.028 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 N007 1.239(3) . ?
O002 N006 1.241(4) . ?
O003 N006 1.238(4) . ?
O004 N007 1.243(3) . ?
N005 N00C 1.329(4) . ?
N005 C00J 1.378(4) . ?
N005 C00M 1.474(4) . ?
N006 C00J 1.391(4) . ?
N007 C00H 1.396(4) . ?
N008 N00B 1.291(4) . ?
N008 C00H 1.354(4) . ?
N009 N00B 1.387(4) . ?
N009 C00I 1.354(4) . ?
N009 C00M 1.433(4) . ?
O00A N00F 1.238(4) . ?
N00C C00K 1.332(4) . ?
N00D C00I 1.318(4) . ?
O00E N00F 1.225(4) . ?
N00F C00K 1.427(5) . ?
N00G C00L 1.339(4) . ?
C00H C00I 1.392(5) . ?
C00J C00L 1.393(5) . ?
C00K C00L 1.405(5) . ?

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
N00C N005 C00J 111.3(3) . . ?
N00C N005 C00M 120.5(3) . . ?
C00J N005 C00M 128.2(3) . . ?
O002 N006 C00J 117.1(3) . . ?
O003 N006 O002 123.1(3) . . ?
O003 N006 C00J 119.8(3) . . ?
O001 N007 O004 123.3(3) . . ?
O001 N007 C00H 119.1(3) . . ?
O004 N007 C00H 117.6(3) . . ?
N00B N008 C00H 108.6(3) . . ?
N00B N009 C00M 119.3(3) . . ?
C00I N009 N00B 111.3(3) . . ?
C00I N009 C00M 128.8(3) . . ?
N008 N00B N009 107.2(3) . . ?
N005 N00C C00K 104.6(3) . . ?
O00A N00F C00K 115.3(3) . . ?
O00E N00F O00A 124.7(3) . . ?
O00E N00F C00K 120.1(3) . . ?
N008 C00H N007 122.5(3) . . ?
N008 C00H C00I 110.9(3) . . ?
C00I C00H N007 126.6(3) . . ?
N009 C00I C00H 102.0(3) . . ?
N00D C00I N009 125.9(3) . . ?
N00D C00I C00H 132.1(3) . . ?
N005 C00J N006 123.8(3) . . ?
N005 C00J C00L 108.3(3) . . ?
N006 C00J C00L 127.8(3) . . ?
N00C C00K N00F 119.6(3) . . ?
N00C C00K C00L 114.3(3) . . ?
C00L C00K N00F 126.1(3) . . ?
N00G C00L C00J 128.3(3) . . ?
N00G C00L C00K 130.2(3) . . ?
C00J C00L C00K 101.5(3) . . ?
N009 C00M N005 110.1(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
