# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_YF_058_a
_database_code_depnum_ccdc_archive 'CCDC 2096613'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-07-15 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N12 O2, C2 H8 N, H2 O'
_chemical_formula_sum            'C7 H13 N13 O3'
_chemical_formula_weight         327.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.4345(5)
_cell_length_b                   9.3017(7)
_cell_length_c                   11.9277(9)
_cell_angle_alpha                76.640(2)
_cell_angle_beta                 84.469(3)
_cell_angle_gamma                81.237(2)
_cell_volume                     685.08(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5444
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5872
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            10334
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.271
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3109
_reflns_number_gt                2457
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.1310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3109
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3789(2) 0.61100(14) 0.33628(11) 0.0260(3) Uani 1 1 d . . . . .
C2 C 0.4453(2) 0.70977(14) 0.47800(10) 0.0248(3) Uani 1 1 d . . . . .
C3 C 0.5931(2) 0.73689(14) 0.38658(11) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.4242(2) 0.75069(14) 0.58840(11) 0.0264(3) Uani 1 1 d . . . . .
C5 C 0.7743(2) 0.81658(14) 0.36847(11) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.13270(18) 0.47772(13) 0.30002(9) 0.0311(3) Uani 1 1 d . . . . .
N2 N 0.29469(17) 0.54478(13) 0.26185(9) 0.0321(3) Uani 1 1 d . . . . .
N3 N 0.31068(16) 0.62821(12) 0.44456(9) 0.0259(2) Uani 1 1 d . . . . .
H3 H 0.203205 0.594329 0.484690 0.031 Uiso 1 1 calc R U . . .
N4 N 0.55121(17) 0.67439(12) 0.29952(9) 0.0291(3) Uani 1 1 d . . . . .
N5 N 0.28125(18) 0.71431(13) 0.67542(10) 0.0334(3) Uani 1 1 d . . . . .
H5 H 0.182460 0.661624 0.675303 0.040 Uiso 1 1 calc R U . . .
N6 N 0.3172(2) 0.77346(15) 0.76281(10) 0.0415(3) Uani 1 1 d . . . . .
N7 N 0.4769(2) 0.84408(15) 0.72906(11) 0.0412(3) Uani 1 1 d . . . . .
N8 N 0.54861(19) 0.83295(13) 0.62084(10) 0.0346(3) Uani 1 1 d . . . . .
N9 N 0.84704(17) 0.88629(12) 0.43951(10) 0.0309(3) Uani 1 1 d . . . . .
H9 H 0.793715 0.891084 0.507702 0.037 Uiso 1 1 calc R U . . .
N10 N 1.01752(18) 0.94800(14) 0.38720(10) 0.0357(3) Uani 1 1 d . . . . .
N11 N 1.04402(19) 0.91459(14) 0.28711(10) 0.0383(3) Uani 1 1 d . . . . .
N12 N 0.89670(19) 0.83321(14) 0.27195(10) 0.0356(3) Uani 1 1 d . . . . .
N13 N 0.7459(2) 0.75498(15) 0.05520(10) 0.0436(3) Uani 1 1 d . . . . .
H13A H 0.729689 0.747265 0.131217 0.052 Uiso 1 1 calc R U . . .
H13B H 0.678526 0.842961 0.021576 0.052 Uiso 1 1 calc R U . . .
C6 C 0.9713(3) 0.7502(3) 0.01917(17) 0.0664(5) Uani 1 1 d . . . . .
H6A H 1.045684 0.656524 0.056443 0.100 Uiso 1 1 calc R U . . .
H6B H 1.025503 0.830049 0.040567 0.100 Uiso 1 1 calc R U . . .
H6C H 0.989903 0.761063 -0.063051 0.100 Uiso 1 1 calc R U . . .
C7 C 0.6492(4) 0.6365(2) 0.02608(16) 0.0625(5) Uani 1 1 d . . . . .
H7A H 0.666568 0.643645 -0.055778 0.094 Uiso 1 1 calc R U . . .
H7B H 0.501697 0.647171 0.049594 0.094 Uiso 1 1 calc R U . . .
H7C H 0.715872 0.541127 0.065375 0.094 Uiso 1 1 calc R U . . .
O1 O 0.05364(16) 0.46152(13) 0.40216(8) 0.0424(3) Uani 1 1 d . . . . .
O2 O 0.04941(18) 0.42410(14) 0.22979(9) 0.0488(3) Uani 1 1 d . . . . .
O3 O 0.6116(2) 0.00979(14) 0.88149(10) 0.0472(3) Uani 1 1 d . . . . .
H3A H 0.558(3) -0.037(2) 0.8347(19) 0.071 Uiso 1 1 d . U . . .
H3B H 0.715(4) 0.037(2) 0.8390(19) 0.071 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.3250(17) . ?
C1 N3 1.3605(16) . ?
C1 N2 1.3814(17) . ?
C2 N3 1.3754(16) . ?
C2 C3 1.3793(19) . ?
C2 C4 1.4418(18) . ?
C3 N4 1.3673(16) . ?
C3 C5 1.4481(19) . ?
C4 N8 1.3262(17) . ?
C4 N5 1.3368(17) . ?
C5 N12 1.3227(18) . ?
C5 N9 1.3343(17) . ?
N1 O1 1.2589(14) . ?
N1 O2 1.2644(15) . ?
N1 N2 1.2877(16) . ?
N3 H3 0.8600 . ?
N5 N6 1.3391(17) . ?
N5 H5 0.8600 . ?
N6 N7 1.2855(18) . ?
N7 N8 1.3499(16) . ?
N9 N10 1.3478(16) . ?
N9 H9 0.8600 . ?
N10 N11 1.2910(17) . ?
N11 N12 1.3488(17) . ?
N13 C7 1.466(2) . ?
N13 C6 1.470(2) . ?
N13 H13A 0.8900 . ?
N13 H13B 0.8900 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
O3 H3A 0.90(2) . ?
O3 H3B 0.83(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 C1 N3 111.29(11) . . ?
N4 C1 N2 117.95(11) . . ?
N3 C1 N2 130.72(12) . . ?
N3 C2 C3 105.30(11) . . ?
N3 C2 C4 123.75(12) . . ?
C3 C2 C4 130.94(12) . . ?
N4 C3 C2 110.30(12) . . ?
N4 C3 C5 117.50(11) . . ?
C2 C3 C5 132.20(12) . . ?
N8 C4 N5 107.84(11) . . ?
N8 C4 C2 124.62(12) . . ?
N5 C4 C2 127.54(12) . . ?
N12 C5 N9 108.07(12) . . ?
N12 C5 C3 123.16(12) . . ?
N9 C5 C3 128.76(12) . . ?
O1 N1 O2 118.31(12) . . ?
O1 N1 N2 124.37(11) . . ?
O2 N1 N2 117.32(11) . . ?
N1 N2 C1 117.54(11) . . ?
C1 N3 C2 107.38(11) . . ?
C1 N3 H3 126.3 . . ?
C2 N3 H3 126.3 . . ?
C1 N4 C3 105.71(11) . . ?
C4 N5 N6 108.73(12) . . ?
C4 N5 H5 125.6 . . ?
N6 N5 H5 125.6 . . ?
N7 N6 N5 106.55(11) . . ?
N6 N7 N8 111.07(11) . . ?
C4 N8 N7 105.82(11) . . ?
C5 N9 N10 109.03(11) . . ?
C5 N9 H9 125.5 . . ?
N10 N9 H9 125.5 . . ?
N11 N10 N9 105.55(11) . . ?
N10 N11 N12 111.65(11) . . ?
C5 N12 N11 105.68(11) . . ?
C7 N13 C6 113.35(15) . . ?
C7 N13 H13A 108.9 . . ?
C6 N13 H13A 108.9 . . ?
C7 N13 H13B 108.9 . . ?
C6 N13 H13B 108.9 . . ?
H13A N13 H13B 107.7 . . ?
N13 C6 H6A 109.5 . . ?
N13 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N13 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N13 C7 H7A 109.5 . . ?
N13 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N13 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H3A O3 H3B 99.1(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C2 C3 N4 0.06(14) . . . . ?
C4 C2 C3 N4 179.16(12) . . . . ?
N3 C2 C3 C5 179.78(13) . . . . ?
C4 C2 C3 C5 -1.1(2) . . . . ?
N3 C2 C4 N8 -177.90(12) . . . . ?
C3 C2 C4 N8 3.1(2) . . . . ?
N3 C2 C4 N5 2.3(2) . . . . ?
C3 C2 C4 N5 -176.64(13) . . . . ?
N4 C3 C5 N12 1.19(19) . . . . ?
C2 C3 C5 N12 -178.52(13) . . . . ?
N4 C3 C5 N9 -179.96(12) . . . . ?
C2 C3 C5 N9 0.3(2) . . . . ?
O1 N1 N2 C1 -4.12(19) . . . . ?
O2 N1 N2 C1 176.36(12) . . . . ?
N4 C1 N2 N1 177.01(11) . . . . ?
N3 C1 N2 N1 -5.4(2) . . . . ?
N4 C1 N3 C2 1.15(14) . . . . ?
N2 C1 N3 C2 -176.53(13) . . . . ?
C3 C2 N3 C1 -0.70(13) . . . . ?
C4 C2 N3 C1 -179.88(11) . . . . ?
N3 C1 N4 C3 -1.08(14) . . . . ?
N2 C1 N4 C3 176.92(11) . . . . ?
C2 C3 N4 C1 0.62(14) . . . . ?
C5 C3 N4 C1 -179.15(11) . . . . ?
N8 C4 N5 N6 -0.33(15) . . . . ?
C2 C4 N5 N6 179.48(12) . . . . ?
C4 N5 N6 N7 0.30(15) . . . . ?
N5 N6 N7 N8 -0.15(16) . . . . ?
N5 C4 N8 N7 0.23(15) . . . . ?
C2 C4 N8 N7 -179.59(12) . . . . ?
N6 N7 N8 C4 -0.05(16) . . . . ?
N12 C5 N9 N10 0.07(15) . . . . ?
C3 C5 N9 N10 -178.91(12) . . . . ?
C5 N9 N10 N11 -0.08(14) . . . . ?
N9 N10 N11 N12 0.06(15) . . . . ?
N9 C5 N12 N11 -0.04(15) . . . . ?
C3 C5 N12 N11 179.02(12) . . . . ?
N10 N11 N12 C5 -0.01(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3B N11 0.83(2) 2.08(2) 2.9000(17) 170(2) 2_766 yes
O3 H3A N7 0.90(2) 2.01(2) 2.9051(18) 172.3(19) 1_545 yes
C6 H6A O2 0.96 2.62 3.468(3) 147.0 1_655 yes
N13 H13B O3 0.89 2.50 3.0895(18) 124.5 2_666 yes
N13 H13B O3 0.89 2.03 2.8475(17) 152.1 1_564 yes
N13 H13A N12 0.89 2.42 3.1183(18) 135.9 . yes
N13 H13A N4 0.89 2.23 3.0325(17) 149.8 . yes
N9 H9 N10 0.86 2.65 3.1043(17) 114.6 2_776 yes
N9 H9 N8 0.86 2.03 2.7577(16) 142.1 . yes
N5 H5 O2 0.86 1.94 2.6760(16) 142.8 2_566 yes
N5 H5 O1 0.86 2.40 3.2143(16) 158.0 2_566 yes
N5 H5 N1 0.86 2.53 3.3806(17) 171.5 2_566 yes
N3 H3 O1 0.86 2.08 2.9325(15) 170.5 2_566 yes
N3 H3 O1 0.86 2.13 2.5885(15) 113.0 . yes

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.044

# start Validation Reply Form
_vrf_PLAT430_YF_058_a            
;
PROBLEM: Short Inter D...A Contact  O1 ..O1    .       2.60 Ang.  
RESPONSE:This is a normal hydrogen bond distance. 
However, in this structure O1 is Nitro O atom, 
there is no H bonding to it.
;
# end Validation Reply Form



####################################################################### 
# 
# 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_2183_0m
_database_code_depnum_ccdc_archive 'CCDC 2102547'
loop_
_audit_author_name
_audit_author_address
'Feng Yang'
;Nanjing University Of Science And Technology
China
;
_audit_update_record             
;
2021-08-11 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_audit_creation_date             2021-08-11
_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         'C2 H6 O S, C5 H4 N12 O2, H2 O'
_chemical_formula_sum            'C7 H12 N12 O4 S'
_chemical_formula_weight         360.35
_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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3452(3)
_cell_length_b                   7.7532(4)
_cell_length_c                   13.1160(6)
_cell_angle_alpha                81.172(2)
_cell_angle_beta                 87.255(2)
_cell_angle_gamma                80.148(2)
_cell_volume                     727.03(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3606
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.391
_cell_measurement_theta_min      2.696
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.0452
_exptl_absorpt_correction_T_min  0.0250
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0910 before and 0.0470 after correction. The Ratio of minimum to maximum transmission is 0.5531. 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    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_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  0.0320
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8362
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_min         2.696
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_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                2432
_reflns_number_total             2956
_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         0.264
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0319P)²+0.3308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N9(H9), N10(H10), N5(H5)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_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
S1 S 0.62913(7) 0.27036(7) 0.01565(4) 0.03745(15) Uani 1 1 d . . . . .
O3 O 0.28366(19) 0.2095(2) 0.15539(10) 0.0411(4) Uani 1 1 d . . . . .
O1 O 0.62034(19) 0.35089(19) 0.11521(10) 0.0402(3) Uani 1 1 d . . . . .
O4 O 0.04208(19) 0.0818(2) 0.18750(11) 0.0466(4) Uani 1 1 d . . . . .
N9 N 0.4675(2) 0.2680(2) 0.30711(11) 0.0288(3) Uani 1 1 d . . . . .
H9 H 0.487068 0.289686 0.239992 0.035 Uiso 1 1 calc R . . . .
O2 O 0.1155(2) 0.0525(2) 0.60179(11) 0.0480(4) Uani 1 1 d . . . . .
H2A H 0.158693 0.079516 0.656832 0.072 Uiso 1 1 d G . . . .
H2B H 0.019139 0.001857 0.618568 0.072 Uiso 1 1 d G . . . .
N10 N 0.3440(2) 0.1853(2) 0.45618(11) 0.0294(3) Uani 1 1 d . . . . .
H10 H 0.267979 0.142862 0.503651 0.035 Uiso 1 1 calc R . . . .
N5 N 0.6928(2) 0.3109(2) 0.61413(11) 0.0317(4) Uani 1 1 d . . . . .
H5 H 0.777599 0.357386 0.574624 0.038 Uiso 1 1 calc R . . . .
N4 N 0.8040(2) 0.4337(2) 0.26126(13) 0.0333(4) Uani 1 1 d . . . . .
N12 N 0.1729(2) 0.1422(2) 0.21704(12) 0.0349(4) Uani 1 1 d . . . . .
N3 N 0.9514(2) 0.5128(2) 0.26819(13) 0.0374(4) Uani 1 1 d . . . . .
N2 N 0.9733(2) 0.5132(2) 0.36561(12) 0.0355(4) Uani 1 1 d . . . . .
N1 N 0.8423(2) 0.4360(2) 0.42339(12) 0.0324(4) Uani 1 1 d . . . . .
N11 N 0.1852(2) 0.1296(2) 0.31982(11) 0.0319(4) Uani 1 1 d . . . . .
N7 N 0.5415(2) 0.2151(2) 0.74599(12) 0.0368(4) Uani 1 1 d . . . . .
N8 N 0.4507(2) 0.1920(2) 0.66206(12) 0.0333(4) Uani 1 1 d . . . . .
N6 N 0.6869(2) 0.2865(2) 0.71771(12) 0.0354(4) Uani 1 1 d . . . . .
C3 C 0.5770(2) 0.3046(2) 0.38182(13) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.5480(2) 0.2527(2) 0.58112(14) 0.0285(4) Uani 1 1 d . . . . .
C5 C 0.3271(2) 0.1942(2) 0.35384(14) 0.0290(4) Uani 1 1 d . . . . .
C2 C 0.4987(2) 0.2526(2) 0.47538(14) 0.0282(4) Uani 1 1 d . . . . .
C4 C 0.7390(2) 0.3873(2) 0.35647(14) 0.0290(4) Uani 1 1 d . . . . .
C6 C 0.7073(3) 0.0401(3) 0.05094(17) 0.0440(5) Uani 1 1 d . . . . .
H6A H 0.824581 0.021936 0.086816 0.066 Uiso 1 1 calc GR . . . .
H6B H 0.725428 -0.017186 -0.011227 0.066 Uiso 1 1 calc GR . . . .
H6C H 0.615013 -0.011552 0.096718 0.066 Uiso 1 1 calc GR . . . .
C7 C 0.8317(3) 0.3305(3) -0.04935(16) 0.0495(6) Uani 1 1 d . . . . .
H7A H 0.813390 0.458944 -0.070549 0.074 Uiso 1 1 calc GR . . . .
H7B H 0.856938 0.270881 -0.110463 0.074 Uiso 1 1 calc GR . . . .
H7C H 0.936481 0.294752 -0.002926 0.074 Uiso 1 1 calc GR . . . .
H4 H 0.759(3) 0.410(3) 0.198(2) 0.063(7) Uiso 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
S1 O1 1.5256(14) . ?
S1 C6 1.775(2) . ?
S1 C7 1.775(2) . ?
O3 N12 1.241(2) . ?
O4 N12 1.240(2) . ?
N9 C3 1.388(2) . ?
N9 C5 1.342(2) . ?
N10 C5 1.344(2) . ?
N10 C2 1.378(2) . ?
N5 N6 1.342(2) . ?
N5 C1 1.338(2) . ?
N4 N3 1.345(2) . ?
N4 C4 1.334(2) . ?
N12 N11 1.343(2) . ?
N3 N2 1.296(2) . ?
N2 N1 1.359(2) . ?
N1 C4 1.324(2) . ?
N11 C5 1.352(2) . ?
N7 N8 1.364(2) . ?
N7 N6 1.298(2) . ?
N8 C1 1.322(2) . ?
C3 C2 1.363(2) . ?
C3 C4 1.448(2) . ?
C1 C2 1.450(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C6 105.97(9) . . ?
O1 S1 C7 104.04(9) . . ?
C7 S1 C6 99.22(11) . . ?
C5 N9 C3 108.92(15) . . ?
C5 N10 C2 109.57(15) . . ?
C1 N5 N6 108.43(15) . . ?
C4 N4 N3 108.36(15) . . ?
O3 N12 N11 122.84(15) . . ?
O4 N12 O3 121.95(16) . . ?
O4 N12 N11 115.20(16) . . ?
N2 N3 N4 106.57(15) . . ?
N3 N2 N1 110.75(14) . . ?
C4 N1 N2 105.50(14) . . ?
N12 N11 C5 116.26(15) . . ?
N6 N7 N8 110.74(15) . . ?
C1 N8 N7 105.34(15) . . ?
N7 N6 N5 106.61(14) . . ?
N9 C3 C4 122.64(16) . . ?
C2 C3 N9 107.09(15) . . ?
C2 C3 C4 130.24(16) . . ?
N5 C1 C2 127.75(16) . . ?
N8 C1 N5 108.88(15) . . ?
N8 C1 C2 123.36(16) . . ?
N9 C5 N10 107.65(15) . . ?
N9 C5 N11 134.08(17) . . ?
N10 C5 N11 118.26(16) . . ?
N10 C2 C1 119.52(16) . . ?
C3 C2 N10 106.76(15) . . ?
C3 C2 C1 133.70(16) . . ?
N4 C4 C3 125.42(16) . . ?
N1 C4 N4 108.82(16) . . ?
N1 C4 C3 125.71(16) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
