# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_output
_database_code_depnum_ccdc_archive 'CCDC 2150373'
loop_
_audit_author_name
_audit_author_address
'Yingying Chai'
;Sichuan University
China
;
_audit_update_record             
;
2022-02-07 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'N3-protonated Cytidine nitrate'
_chemical_formula_moiety         'C9 H14 N3 O5, N O3'
_chemical_formula_sum            'C9 H14 N4 O8'
_chemical_formula_weight         306.24
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7120(15)
_cell_length_b                   7.4810(15)
_cell_length_c                   11.062(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.44(3)
_cell_angle_gamma                90
_cell_volume                     605.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1531
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      1.941
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull dark black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             320
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.051
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            1531
_diffrn_reflns_point_group_measured_fraction_full 0.537
_diffrn_reflns_point_group_measured_fraction_max 0.534
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.840
_diffrn_reflns_theta_min         1.941
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    0.000
_reflns_Friedel_fraction_max     0.000
_reflns_number_gt                1510
_reflns_number_total             1531
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1531
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.074
_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)+(0.0587P)²+0.1602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0843
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C6(H6), C8(H8), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3)
2.d Idealised tetrahedral OH refined as rotating group:
 O14(H14), O17(H17), O16(H16), N10(H10A)
;
_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
O15 O -0.53624(18) -0.30605(19) -0.79162(12) 0.0138(3) Uani 1 1 d . . . . .
O13 O -0.6891(2) -0.7367(2) -0.62528(13) 0.0169(3) Uani 1 1 d . . . . .
O14 O -0.6796(2) -0.6377(2) -0.94928(13) 0.0168(3) Uani 1 1 d . . . . .
H14 H -0.744373 -0.641277 -1.026228 0.025 Uiso 1 1 calc R U . . .
O19 O -0.83654(19) -0.8650(2) -0.38660(12) 0.0169(3) Uani 1 1 d . . . . .
O17 O -0.74968(19) 0.0133(2) -0.83342(13) 0.0170(3) Uani 1 1 d . . . . .
H17 H -0.707904 0.111158 -0.799211 0.025 Uiso 1 1 calc R U . . .
O16 O -0.89528(18) -0.3671(2) -1.08456(11) 0.0156(3) Uani 1 1 d . . . . .
H16 H -1.003973 -0.402466 -1.103349 0.023 Uiso 1 1 calc R U . . .
O20 O -0.8611(2) -0.7239(2) -0.22026(14) 0.0183(3) Uani 1 1 d . . . . .
O21 O -0.8752(2) -1.0137(2) -0.22947(15) 0.0232(3) Uani 1 1 d . . . . .
N11 N -0.7505(2) -0.5532(2) -0.47913(16) 0.0152(3) Uani 1 1 d . . . . .
N18 N -0.8567(2) -0.8680(3) -0.27784(15) 0.0147(3) Uani 1 1 d . . . . .
N12 N -0.6744(2) -0.4344(2) -0.65089(15) 0.0136(3) Uani 1 1 d . . . . .
N10 N -0.8207(3) -0.3759(3) -0.33088(16) 0.0197(4) Uani 1 1 d . . . . .
H10A H -0.835300 -0.478698 -0.305193 0.030 Uiso 1 1 calc R U . . .
C7 C -0.8213(2) -0.3461(3) -0.95053(16) 0.0123(3) Uani 1 1 d . . . . .
H7 H -0.909502 -0.281880 -0.916306 0.015 Uiso 1 1 calc R U . . .
C2 C -0.7035(3) -0.5851(3) -0.58841(18) 0.0143(4) Uani 1 1 d . . . . .
C6 C -0.7634(2) -0.5238(3) -0.88086(16) 0.0135(4) Uani 1 1 d . . . . .
H6 H -0.865691 -0.583778 -0.859243 0.016 Uiso 1 1 calc R U . . .
C8 C -0.6404(2) -0.2446(3) -0.91807(17) 0.0128(3) Uani 1 1 d . . . . .
H8 H -0.575186 -0.281801 -0.979061 0.015 Uiso 1 1 calc R U . . .
C5 C -0.6087(3) -0.4661(3) -0.76260(17) 0.0132(3) Uani 1 1 d . . . . .
H5 H -0.511395 -0.559919 -0.740478 0.016 Uiso 1 1 calc R U . . .
C9 C -0.6484(3) -0.0431(3) -0.91617(19) 0.0167(4) Uani 1 1 d . . . . .
H9A H -0.522967 0.006413 -0.885306 0.020 Uiso 1 1 calc R U . . .
H9B H -0.708496 0.002426 -1.003470 0.020 Uiso 1 1 calc R U . . .
C4 C -0.7540(3) -0.2375(3) -0.50755(18) 0.0159(4) Uani 1 1 d . . . . .
H4 H -0.774613 -0.119838 -0.482727 0.019 Uiso 1 1 calc R U . . .
C1 C -0.7766(2) -0.3885(3) -0.43613(18) 0.0161(4) Uani 1 1 d . . . . .
C3 C -0.7023(3) -0.2662(3) -0.61198(18) 0.0150(4) Uani 1 1 d . . . . .
H3 H -0.684795 -0.166284 -0.659867 0.018 Uiso 1 1 calc R U . . .
H10B H -0.841(5) -0.259(7) -0.298(4) 0.046(10) Uiso 1 1 d . . . . .
H11 H -0.772(4) -0.648(5) -0.445(3) 0.018(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
O15 C8 1.450(2) . ?
O15 C5 1.401(2) . ?
O13 C2 1.222(3) . ?
O14 H14 0.8400 . ?
O14 C6 1.423(2) . ?
O19 N18 1.261(2) . ?
O17 H17 0.8400 . ?
O17 C9 1.442(2) . ?
O16 H16 0.8400 . ?
O16 C7 1.419(2) . ?
O20 N18 1.258(2) . ?
O21 N18 1.242(2) . ?
N11 C2 1.388(2) . ?
N11 C1 1.358(3) . ?
N11 H11 0.84(3) . ?
N12 C2 1.377(2) . ?
N12 C5 1.495(2) . ?
N12 C3 1.369(3) . ?
N10 H10A 0.8400 . ?
N10 C1 1.316(2) . ?
N10 H10B 0.98(5) . ?
C7 H7 1.0000 . ?
C7 C6 1.530(3) . ?
C7 C8 1.529(3) . ?
C6 H6 1.0000 . ?
C6 C5 1.528(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.509(3) . ?
C5 H5 1.0000 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C1 1.421(3) . ?
C4 C3 1.353(3) . ?
C3 H3 0.9500 . ?

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
C5 O15 C8 110.67(14) . . ?
C6 O14 H14 109.5 . . ?
C9 O17 H17 109.5 . . ?
C7 O16 H16 109.5 . . ?
C2 N11 H11 113(2) . . ?
C1 N11 C2 124.70(17) . . ?
C1 N11 H11 122(2) . . ?
O20 N18 O19 119.94(17) . . ?
O21 N18 O19 119.46(17) . . ?
O21 N18 O20 120.59(14) . . ?
C2 N12 C5 115.89(16) . . ?
C3 N12 C2 121.89(16) . . ?
C3 N12 C5 122.22(16) . . ?
H10A N10 H10B 129.8 . . ?
C1 N10 H10A 109.5 . . ?
C1 N10 H10B 121(2) . . ?
O16 C7 H7 110.6 . . ?
O16 C7 C6 112.77(15) . . ?
O16 C7 C8 109.62(14) . . ?
C6 C7 H7 110.6 . . ?
C8 C7 H7 110.6 . . ?
C8 C7 C6 102.37(14) . . ?
O13 C2 N11 121.77(18) . . ?
O13 C2 N12 123.08(17) . . ?
N12 C2 N11 115.15(17) . . ?
O14 C6 C7 111.19(14) . . ?
O14 C6 H6 112.6 . . ?
O14 C6 C5 105.18(15) . . ?
C7 C6 H6 112.6 . . ?
C5 C6 C7 102.12(15) . . ?
C5 C6 H6 112.6 . . ?
O15 C8 C7 104.75(14) . . ?
O15 C8 H8 108.6 . . ?
O15 C8 C9 108.43(17) . . ?
C7 C8 H8 108.6 . . ?
C9 C8 C7 117.48(17) . . ?
C9 C8 H8 108.6 . . ?
O15 C5 N12 108.56(15) . . ?
O15 C5 C6 107.79(14) . . ?
O15 C5 H5 109.5 . . ?
N12 C5 C6 112.04(15) . . ?
N12 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
O17 C9 C8 109.51(16) . . ?
O17 C9 H9A 109.8 . . ?
O17 C9 H9B 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C1 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C1 118.00(19) . . ?
N11 C1 C4 117.97(17) . . ?
N10 C1 N11 118.92(19) . . ?
N10 C1 C4 123.11(19) . . ?
N12 C3 H3 118.9 . . ?
C4 C3 N12 122.16(19) . . ?
C4 C3 H3 118.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O15 C8 C9 O17 -64.9(2) . . . . ?
O14 C6 C5 O15 91.79(17) . . . . ?
O14 C6 C5 N12 -148.82(15) . . . . ?
O16 C7 C6 O14 39.7(2) . . . . ?
O16 C7 C6 C5 151.43(14) . . . . ?
O16 C7 C8 O15 -152.02(14) . . . . ?
O16 C7 C8 C9 87.6(2) . . . . ?
C7 C6 C5 O15 -24.40(18) . . . . ?
C7 C6 C5 N12 94.99(17) . . . . ?
C7 C8 C9 O17 53.5(2) . . . . ?
C2 N11 C1 N10 -179.90(18) . . . . ?
C2 N11 C1 C4 -0.1(3) . . . . ?
C2 N12 C5 O15 -163.01(15) . . . . ?
C2 N12 C5 C6 78.1(2) . . . . ?
C2 N12 C3 C4 2.3(3) . . . . ?
C6 C7 C8 O15 -32.10(17) . . . . ?
C6 C7 C8 C9 -152.45(17) . . . . ?
C8 O15 C5 N12 -117.21(16) . . . . ?
C8 O15 C5 C6 4.36(19) . . . . ?
C8 C7 C6 O14 -78.02(17) . . . . ?
C8 C7 C6 C5 33.72(16) . . . . ?
C5 O15 C8 C7 17.76(18) . . . . ?
C5 O15 C8 C9 143.96(16) . . . . ?
C5 N12 C2 O13 -4.8(3) . . . . ?
C5 N12 C2 N11 175.15(16) . . . . ?
C5 N12 C3 C4 -177.01(16) . . . . ?
C1 N11 C2 O13 -176.95(19) . . . . ?
C1 N11 C2 N12 3.1(3) . . . . ?
C1 C4 C3 N12 1.0(3) . . . . ?
C3 N12 C2 O13 175.92(19) . . . . ?
C3 N12 C2 N11 -4.2(3) . . . . ?
C3 N12 C5 O15 16.3(2) . . . . ?
C3 N12 C5 C6 -102.6(2) . . . . ?
C3 C4 C1 N11 -2.0(3) . . . . ?
C3 C4 C1 N10 177.76(18) . . . . ?

_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_ango3_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2150374'
loop_
_audit_author_name
_audit_author_address
'Yingying Chai'
;Sichuan University
China
;
_audit_update_record             
;
2022-02-07 deposited with the CCDC.	2023-11-01 downloaded from the CCDC.
;
_audit_creation_date             2021-09-06
_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        'Cytidine and silver nitrate'
_chemical_formula_moiety         'C9 H13 Ag N4 O8'
_chemical_formula_sum            'C9 H13 Ag N4 O8'
_chemical_formula_weight         413.10
_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 0.0037 0.0017 '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'
Ag Ag -0.8238 1.1495 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0070 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0123 0.0065 '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                   4.6969(3)
_cell_length_b                   15.1122(11)
_cell_length_c                   17.3305(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1230.13(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.761
_cell_measurement_theta_min      2.780
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    1.800
_exptl_absorpt_correction_T_max  0.0233
_exptl_absorpt_correction_T_min  0.0070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1731 before and 0.0716 after correction. The Ratio of minimum to maximum transmission is 0.3004. 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    2.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16250
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.949
_diffrn_reflns_theta_max         26.761
_diffrn_reflns_theta_min         2.780
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.72929
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2269
_reflns_number_total             2401
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.960
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.172
_refine_ls_abs_structure_details 
;
 Flack x determined using 888 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.162
_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)+(0.0793P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1146
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C5(H5A), C7(H7A), C6(H6A)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6), O7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Ag01 Ag 0.48603(11) 0.19356(3) 0.98100(3) 0.0260(2) Uani 1 1 d . . . . .
O1 O 0.3711(11) 0.2707(3) 0.8773(3) 0.0245(10) Uani 1 1 d . . . . .
O5 O 0.5871(11) 0.1755(3) 0.6865(3) 0.0271(11) Uani 1 1 d . . . . .
H5 H 0.685537 0.165907 0.726120 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.9580(12) 0.1263(4) 0.9489(3) 0.0300(11) Uani 1 1 d . . . . .
N3 N 0.2635(14) 0.3687(4) 0.7851(3) 0.0218(12) Uani 1 1 d . . . . .
O6 O 0.1894(10) 0.1920(4) 0.5761(3) 0.0252(10) Uani 1 1 d . . . . .
H6 H 0.348017 0.178929 0.556805 0.038 Uiso 1 1 calc GR . . . .
N2 N 0.0227(14) 0.3708(4) 0.9051(3) 0.0232(11) Uani 1 1 d . . . . .
O8 O 0.5353(11) 0.3746(3) 0.6701(2) 0.0233(10) Uani 1 1 d . . . . .
O7 O 0.1939(10) 0.3782(3) 0.4801(3) 0.0246(10) Uani 1 1 d . . . . .
H7 H 0.338406 0.365252 0.453845 0.037 Uiso 1 1 calc GR . . . .
N4 N 1.0015(15) 0.1118(4) 0.8771(3) 0.0268(12) Uani 1 1 d . . . . .
O4 O 1.2123(13) 0.0678(4) 0.8579(3) 0.0374(13) Uani 1 1 d . . . . .
O3 O 0.8364(14) 0.1443(5) 0.8297(3) 0.0446(16) Uani 1 1 d . . . . .
N1 N -0.3215(13) 0.4758(4) 0.9279(3) 0.0281(14) Uani 1 1 d . . . . .
H1A H -0.356399 0.450428 0.972606 0.034 Uiso 1 1 calc R . . . .
H1B H -0.418662 0.522862 0.913778 0.034 Uiso 1 1 calc R . . . .
C1 C -0.1219(16) 0.4429(5) 0.8816(4) 0.0246(14) Uani 1 1 d . . . . .
C9 C 0.2806(15) 0.4086(5) 0.5547(4) 0.0227(14) Uani 1 1 d . . . . .
H9A H 0.112353 0.430811 0.583118 0.027 Uiso 1 1 calc R . . . .
H9B H 0.416089 0.458326 0.548639 0.027 Uiso 1 1 calc R . . . .
C8 C 0.4209(15) 0.3352(5) 0.6009(4) 0.0219(14) Uani 1 1 d . . . . .
H8 H 0.579300 0.308719 0.570065 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2220(16) 0.3346(5) 0.8584(4) 0.0218(14) Uani 1 1 d . . . . .
C5 C 0.4764(15) 0.3219(4) 0.7358(4) 0.0217(13) Uani 1 1 d . . . . .
H5A H 0.655351 0.311508 0.765701 0.026 Uiso 1 1 calc R . . . .
C2 C -0.0601(16) 0.4840(4) 0.8091(4) 0.0253(15) Uani 1 1 d . . . . .
H2 H -0.150850 0.537543 0.794231 0.030 Uiso 1 1 calc R . . . .
C3 C 0.1301(18) 0.4444(5) 0.7630(4) 0.0288(16) Uani 1 1 d . . . . .
H3 H 0.172432 0.469568 0.714050 0.035 Uiso 1 1 calc R . . . .
C7 C 0.2240(15) 0.2619(5) 0.6294(4) 0.0227(13) Uani 1 1 d . . . . .
H7A H 0.032891 0.288054 0.640649 0.027 Uiso 1 1 calc R . . . .
C6 C 0.3604(16) 0.2334(5) 0.7053(4) 0.0231(14) Uani 1 1 d . . . . .
H6A H 0.220201 0.205720 0.741387 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
Ag01 Ag01 2.9764(6) 4_557 ?
Ag01 Ag01 2.9764(6) 4_457 ?
Ag01 O1 2.208(5) . ?
Ag01 O2 2.502(6) . ?
Ag01 N2 2.207(5) 4_557 ?
O1 C4 1.238(9) . ?
O5 H5 0.8400 . ?
O5 C6 1.415(9) . ?
O2 N4 1.279(7) . ?
N3 C4 1.385(8) . ?
N3 C5 1.494(9) . ?
N3 C3 1.360(10) . ?
O6 H6 0.8400 . ?
O6 C7 1.413(8) . ?
N2 C1 1.348(9) . ?
N2 C4 1.352(9) . ?
O8 C8 1.442(7) . ?
O8 C5 1.417(7) . ?
O7 H7 0.8400 . ?
O7 C9 1.432(8) . ?
N4 O4 1.238(9) . ?
N4 O3 1.233(9) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C1 1.329(9) . ?
C1 C2 1.431(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.519(10) . ?
C8 H8 1.0000 . ?
C8 C7 1.525(10) . ?
C5 H5A 1.0000 . ?
C5 C6 1.538(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.341(10) . ?
C3 H3 0.9500 . ?
C7 H7A 1.0000 . ?
C7 C6 1.525(10) . ?
C6 H6A 1.0000 . ?

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
Ag01 Ag01 Ag01 104.19(3) 4_457 4_557 ?
O1 Ag01 Ag01 94.03(15) . 4_557 ?
O1 Ag01 Ag01 71.62(13) . 4_457 ?
O1 Ag01 O2 104.48(18) . . ?
O1 Ag01 N2 168.3(2) . 4_557 ?
O2 Ag01 Ag01 168.92(13) . 4_457 ?
O2 Ag01 Ag01 65.35(12) . 4_557 ?
N2 Ag01 Ag01 89.61(17) 4_557 4_557 ?
N2 Ag01 Ag01 96.67(16) 4_557 4_457 ?
N2 Ag01 O2 87.2(2) 4_557 . ?
C4 O1 Ag01 140.0(4) . . ?
C6 O5 H5 109.5 . . ?
N4 O2 Ag01 115.3(5) . . ?
C4 N3 C5 116.3(6) . . ?
C3 N3 C4 120.5(6) . . ?
C3 N3 C5 123.0(6) . . ?
C7 O6 H6 109.5 . . ?
C1 N2 Ag01 126.0(5) . 4_457 ?
C1 N2 C4 119.7(6) . . ?
C4 N2 Ag01 114.3(4) . 4_457 ?
C5 O8 C8 111.3(5) . . ?
C9 O7 H7 109.5 . . ?
O4 N4 O2 118.8(6) . . ?
O3 N4 O2 118.7(7) . . ?
O3 N4 O4 122.5(6) . . ?
H1A N1 H1B 120.0 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
N2 C1 C2 120.9(6) . . ?
N1 C1 N2 118.4(6) . . ?
N1 C1 C2 120.7(6) . . ?
O7 C9 H9A 109.3 . . ?
O7 C9 H9B 109.3 . . ?
O7 C9 C8 111.4(6) . . ?
H9A C9 H9B 108.0 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
O8 C8 C9 107.4(5) . . ?
O8 C8 H8 109.4 . . ?
O8 C8 C7 104.9(5) . . ?
C9 C8 H8 109.4 . . ?
C9 C8 C7 116.0(6) . . ?
C7 C8 H8 109.4 . . ?
O1 C4 N3 116.9(6) . . ?
O1 C4 N2 123.3(6) . . ?
N2 C4 N3 119.7(6) . . ?
N3 C5 H5A 109.9 . . ?
N3 C5 C6 111.8(6) . . ?
O8 C5 N3 108.9(5) . . ?
O8 C5 H5A 109.9 . . ?
O8 C5 C6 106.4(5) . . ?
C6 C5 H5A 109.9 . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.7(6) . . ?
C3 C2 H2 121.1 . . ?
N3 C3 H3 119.5 . . ?
C2 C3 N3 120.9(7) . . ?
C2 C3 H3 119.5 . . ?
O6 C7 C8 113.7(5) . . ?
O6 C7 H7A 108.7 . . ?
O6 C7 C6 113.6(6) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 C6 103.2(5) . . ?
C6 C7 H7A 108.7 . . ?
O5 C6 C5 110.5(6) . . ?
O5 C6 C7 107.0(6) . . ?
O5 C6 H6A 112.4 . . ?
C5 C6 H6A 112.4 . . ?
C7 C6 C5 101.5(6) . . ?
C7 C6 H6A 112.4 . . ?

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
Ag01 O1 C4 N3 168.2(5) . . . . ?
Ag01 O1 C4 N2 -12.8(12) . . . . ?
Ag01 O2 N4 O4 -170.3(5) . . . . ?
Ag01 O2 N4 O3 11.9(8) . . . . ?
Ag01 N2 C1 N1 -5.4(9) 4_457 . . . ?
Ag01 N2 C1 C2 173.8(5) 4_457 . . . ?
Ag01 N2 C4 O1 0.3(9) 4_457 . . . ?
Ag01 N2 C4 N3 179.4(5) 4_457 . . . ?
N3 C5 C6 O5 -156.5(5) . . . . ?
N3 C5 C6 C7 90.3(6) . . . . ?
O6 C7 C6 O5 42.8(8) . . . . ?
O6 C7 C6 C5 158.6(6) . . . . ?
N2 C1 C2 C3 5.1(11) . . . . ?
O8 C8 C7 O6 -153.4(5) . . . . ?
O8 C8 C7 C6 -29.9(7) . . . . ?
O8 C5 C6 O5 84.7(6) . . . . ?
O8 C5 C6 C7 -28.5(7) . . . . ?
O7 C9 C8 O8 172.2(5) . . . . ?
O7 C9 C8 C7 -70.9(7) . . . . ?
N1 C1 C2 C3 -175.7(7) . . . . ?
C1 N2 C4 O1 176.9(7) . . . . ?
C1 N2 C4 N3 -4.0(10) . . . . ?
C1 C2 C3 N3 -1.2(11) . . . . ?
C9 C8 C7 O6 88.3(7) . . . . ?
C9 C8 C7 C6 -148.2(6) . . . . ?
C8 O8 C5 N3 -110.2(6) . . . . ?
C8 O8 C5 C6 10.5(7) . . . . ?
C8 C7 C6 O5 -80.8(7) . . . . ?
C8 C7 C6 C5 35.0(7) . . . . ?
C4 N3 C5 O8 -168.2(6) . . . . ?
C4 N3 C5 C6 74.5(7) . . . . ?
C4 N3 C3 C2 -5.1(11) . . . . ?
C4 N2 C1 N1 178.4(7) . . . . ?
C4 N2 C1 C2 -2.4(10) . . . . ?
C5 N3 C4 O1 2.4(9) . . . . ?
C5 N3 C4 N2 -176.8(6) . . . . ?
C5 N3 C3 C2 179.8(7) . . . . ?
C5 O8 C8 C9 136.1(6) . . . . ?
C5 O8 C8 C7 12.2(7) . . . . ?
C3 N3 C4 O1 -173.0(7) . . . . ?
C3 N3 C4 N2 7.9(11) . . . . ?
C3 N3 C5 O8 7.1(9) . . . . ?
C3 N3 C5 C6 -110.2(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
