# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ag-2a_tw
_database_code_depnum_ccdc_archive 'CCDC 1966842'
loop_
_audit_author_name
_audit_author_address
MaCaoa
;NingXia university
China
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H4 Ag N4 O2'
_chemical_formula_sum            'C3 H4 Ag N4 O2'
_chemical_formula_weight         235.97
_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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8458(15)
_cell_length_b                   6.0291(10)
_cell_length_c                   10.7271(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.815(17)
_cell_angle_gamma                90
_cell_volume                     553.08(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2021
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6740
_cell_measurement_theta_min      3.8740
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.842
_exptl_absorpt_coefficient_mu    3.573
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.834
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1364
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.468
_diffrn_reflns_theta_min         2.382
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega 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    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1145
_reflns_number_total             1364
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         2.835
_refine_diff_density_min         -1.787
_refine_diff_density_rms         0.349
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1364
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.053
_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)+(0.0494P)²+7.2355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1342
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.557(5)
 0.443(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
4.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Ag1 Ag 0.58733(7) 0.54905(10) 0.19533(6) 0.0131(2) Uani 1 1 d . . . . .
O2 O 1.0852(6) 0.8326(10) 0.6469(6) 0.0145(12) Uani 1 1 d . . . . .
H2 H 1.112674 0.753709 0.594428 0.022 Uiso 1 1 calc GR . . . .
N2 N 0.6388(8) 0.4539(11) 0.3998(7) 0.0088(13) Uani 1 1 d . U . . .
N3 N 0.5807(7) 0.2675(12) 0.4389(6) 0.0116(13) Uani 1 1 d . . . . .
O1 O 0.8736(7) 0.8355(11) 0.7238(6) 0.0174(13) Uani 1 1 d . . . . .
N4 N 0.6485(8) 0.2315(12) 0.5614(7) 0.0139(14) Uani 1 1 d . . . . .
C1 C 0.9342(9) 0.8027(13) 0.6365(8) 0.0106(15) Uani 1 1 d . . . . .
C3 C 0.7512(8) 0.3886(12) 0.6051(7) 0.0052(13) Uani 1 1 d . U . . .
H3 H 0.814304 0.403105 0.688494 0.006 Uiso 1 1 calc R . . . .
N1 N 0.7465(9) 0.5250(13) 0.5040(8) 0.0195(16) Uani 1 1 d . . . . .
C2 C 0.8459(9) 0.7263(15) 0.5026(8) 0.0143(16) Uani 1 1 d . . . . .
H2A H 0.779641 0.846365 0.459676 0.017 Uiso 1 1 calc R . . . .
H2B H 0.920534 0.693533 0.452772 0.017 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ag1 0.0134(3) 0.0157(4) 0.0092(3) 0.0015(2) 0.0010(3) 0.0022(2)
O2 0.012(3) 0.017(3) 0.016(3) -0.003(2) 0.007(2) -0.001(2)
N2 0.0082(15) 0.0094(16) 0.0087(16) 0.0000(9) 0.0019(10) -0.0002(9)
N3 0.012(3) 0.014(3) 0.007(3) 0.002(3) 0.000(3) 0.003(3)
O1 0.012(3) 0.027(4) 0.014(3) 0.000(3) 0.004(2) -0.003(2)
N4 0.012(3) 0.017(4) 0.011(3) 0.001(3) 0.000(3) -0.001(3)
C1 0.010(3) 0.011(4) 0.008(4) 0.000(3) -0.002(3) 0.000(3)
C3 0.0054(15) 0.0052(16) 0.0050(16) 0.0005(10) 0.0014(10) -0.0006(10)
N1 0.018(4) 0.024(4) 0.017(4) 0.003(3) 0.004(3) 0.005(3)
C2 0.012(3) 0.016(4) 0.015(4) 0.001(3) 0.002(3) -0.005(3)

_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
Ag1 N2 2.199(7) . ?
Ag1 N3 2.219(7) 2_655 ?
Ag1 O1 2.568(6) 4_575 ?
Ag1 N4 2.370(7) 4_565 ?
O2 H2 0.8200 . ?
O2 C1 1.324(9) . ?
N2 N3 1.347(9) . ?
N2 N1 1.340(10) . ?
N3 N4 1.315(9) . ?
O1 C1 1.208(10) . ?
N4 C3 1.313(10) . ?
C1 C2 1.521(12) . ?
C3 H3 0.9300 . ?
C3 N1 1.353(11) . ?
N1 C2 1.501(11) . ?
C2 H2A 0.9700 . ?
C2 H2B 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
N2 Ag1 N3 137.3(2) . 2_655 ?
N2 Ag1 O1 90.3(2) . 4_575 ?
N2 Ag1 N4 113.4(2) . 4_565 ?
N3 Ag1 O1 113.1(2) 2_655 4_575 ?
N3 Ag1 N4 104.4(2) 2_655 4_565 ?
N4 Ag1 O1 83.9(2) 4_565 4_575 ?
C1 O2 H2 109.5 . . ?
N3 N2 Ag1 122.0(5) . . ?
N1 N2 Ag1 132.1(5) . . ?
N1 N2 N3 104.7(6) . . ?
N2 N3 Ag1 122.6(5) . 2_645 ?
N4 N3 Ag1 127.5(6) . 2_645 ?
N4 N3 N2 109.6(6) . . ?
C1 O1 Ag1 124.9(5) . 4_576 ?
N3 N4 Ag1 127.4(5) . 4_566 ?
C3 N4 Ag1 122.9(5) . 4_566 ?
C3 N4 N3 109.5(7) . . ?
O2 C1 C2 112.6(7) . . ?
O1 C1 O2 123.4(8) . . ?
O1 C1 C2 124.0(7) . . ?
N4 C3 H3 127.0 . . ?
N4 C3 N1 106.0(7) . . ?
N1 C3 H3 127.0 . . ?
N2 N1 C3 110.1(7) . . ?
N2 N1 C2 122.9(7) . . ?
C3 N1 C2 127.0(7) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
N1 C2 C1 113.3(7) . . ?
N1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?

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
C3 H3 O2 0.93 1.81 2.705(10) 160.0 2_746 yes

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
Ag1 N2 N3 Ag1 -4.9(8) . . . 2_645 ?
Ag1 N2 N3 N4 170.0(5) . . . . ?
Ag1 N2 N1 C3 -168.7(5) . . . . ?
Ag1 N2 N1 C2 10.5(11) . . . . ?
Ag1 N3 N4 Ag1 -11.0(9) 2_645 . . 4_566 ?
Ag1 N3 N4 C3 174.1(5) 2_645 . . . ?
Ag1 O1 C1 O2 151.4(6) 4_576 . . . ?
Ag1 O1 C1 C2 -27.6(11) 4_576 . . . ?
Ag1 N4 C3 N1 -175.7(5) 4_566 . . . ?
O2 C1 C2 N1 129.4(7) . . . . ?
N2 N3 N4 Ag1 174.5(5) . . . 4_566 ?
N2 N3 N4 C3 -0.4(9) . . . . ?
N2 N1 C2 C1 167.8(7) . . . . ?
N3 N2 N1 C3 -1.6(8) . . . . ?
N3 N2 N1 C2 177.6(7) . . . . ?
N3 N4 C3 N1 -0.6(9) . . . . ?
O1 C1 C2 N1 -51.5(11) . . . . ?
N4 C3 N1 N2 1.4(9) . . . . ?
N4 C3 N1 C2 -177.8(8) . . . . ?
C3 N1 C2 C1 -13.1(12) . . . . ?
N1 N2 N3 Ag1 -173.7(5) . . . 2_645 ?
N1 N2 N3 N4 1.2(8) . . . . ?

_shelx_res_file                  
;
TITL ag-2a_a.res in P2(1)/c
    ag-2a_tw.res
    created by SHELXL-2018/3 at 15:51:36 on 17-Jul-2018
REM Old TITL Ag-2a in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.119, Rweak 0.036, Alpha 0.095
REM <I/s> 0.800 for 116 systematic absences, Orientation as input
REM Formula found by SHELXT: C9 N2 O2 Ag
CELL 0.71073 8.8458 6.0291 10.7271 90 104.815 90
ZERR 4 0.0015 0.001 0.0018 0 0.017 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Ag N O
UNIT 12 16 4 16 8
EQIV $1 2-X,-0.5+Y,1.5-Z
ISOR 0.001 0.002 C3
ISOR 0.001 0.002 N2

L.S. 10
PLAN  5
SIZE 0.03 0.04 0.05
HTAB C3 O2_$1
BOND $H
LIST 4
CONF
fmap 2
acta
OMIT 3 1 5
OMIT -2 1 5
OMIT -8 1 5
OMIT 1 4 5
OMIT 1 2 5
OMIT -3 3 5
OMIT 0 6 5
OMIT -6 4 5
OMIT 4 0 2
OMIT -7 3 5
OMIT -10 1 7
OMIT 2 2 5
OMIT -5 2 5
REM <olex2.extras>
REM <HklSrc "%.\\Ag-2a_tw.hkl">
REM </olex2.extras>

WGHT    0.049400    7.235500
BASF   0.44285
FVAR      12.83061
AG1   3    0.587330    0.549050    0.195334    11.00000    0.01337    0.01572 =
         0.00917    0.00146    0.00101    0.00222
O2    5    1.085151    0.832566    0.646913    11.00000    0.01163    0.01699 =
         0.01643   -0.00264    0.00665   -0.00105
AFIX 147
H2    2    1.112674    0.753709    0.594428    11.00000   -1.50000
AFIX   0
N2    4    0.638786    0.453932    0.399825    11.00000    0.00824    0.00941 =
         0.00871    0.00002    0.00192   -0.00023
N3    4    0.580725    0.267481    0.438903    11.00000    0.01237    0.01424 =
         0.00679    0.00239   -0.00023    0.00284
O1    5    0.873597    0.835517    0.723796    11.00000    0.01216    0.02674 =
         0.01383   -0.00028    0.00413   -0.00278
N4    4    0.648466    0.231510    0.561371    11.00000    0.01204    0.01702 =
         0.01137    0.00136    0.00043   -0.00079
C1    1    0.934188    0.802677    0.636490    11.00000    0.00998    0.01150 =
         0.00768    0.00026   -0.00233   -0.00047
C3    1    0.751178    0.388583    0.605061    11.00000    0.00543    0.00517 =
         0.00496    0.00053    0.00136   -0.00063
AFIX  43
H3    2    0.814304    0.403105    0.688494    11.00000   -1.20000
AFIX   0
N1    4    0.746482    0.524996    0.503996    11.00000    0.01761    0.02365 =
         0.01716    0.00324    0.00408    0.00466
C2    1    0.845859    0.726299    0.502552    11.00000    0.01182    0.01583 =
         0.01452    0.00078    0.00196   -0.00457
AFIX  23
H2A   2    0.779641    0.846365    0.459676    11.00000   -1.20000
H2B   2    0.920534    0.693533    0.452772    11.00000   -1.20000
AFIX   0
HKLF 5




REM  ag-2a_a.res in P2(1)/c
REM wR2 = 0.1397, GooF = S = 1.058, Restrained GooF = 1.053 for all data
REM R1 = 0.0562 for 1145 Fo > 4sig(Fo) and 0.0636 for all 1364 data
REM 93 parameters refined using 12 restraints

END

WGHT      0.0494      7.2334

REM Highest difference peak  2.835,  deepest hole -1.787,  1-sigma level  0.349
Q1    1   0.7598  1.0462  0.3784  11.00000  0.05    2.83
Q2    1   0.5903  0.5412  0.6093  11.00000  0.05    2.45
Q3    1   0.4144  0.4515  0.2218  11.00000  0.05    1.97
Q4    1   0.7556  0.4498  0.2906  11.00000  0.05    1.65
Q5    1   0.7625  0.0335  0.5753  11.00000  0.05    1.44
;
_shelx_res_checksum              46534
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.557(5)
2 0.443(5)

####################################################################### 
# 
# 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_22qq
_database_code_depnum_ccdc_archive 'CCDC 1966847'
loop_
_audit_author_name
_audit_author_address
macaob
;NingXia university
China
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-01-20 downloaded from the CCDC.
;
_audit_creation_date             2018-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H4 Ag N5 O2'
_chemical_formula_sum            'C3 H4 Ag N5 O2'
_chemical_formula_weight         249.98
_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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.2779(9)
_cell_length_b                   10.937(2)
_cell_length_c                   14.054(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.837(8)
_cell_angle_gamma                90
_cell_volume                     632.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5091
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.559
_cell_measurement_theta_min      3.014
_shelx_estimated_absorpt_T_max   0.618
_shelx_estimated_absorpt_T_min   0.587
_exptl_absorpt_coefficient_mu    3.136
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1076 before and 0.0771 after correction.
The Ratio of minimum to maximum transmission is 0.7967.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.625
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10565
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         3.013
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                978
_reflns_number_total             1113
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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         5.886
_refine_diff_density_min         -1.346
_refine_diff_density_rms         0.437
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1113
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.1073
_refine_ls_restrained_S_all      1.216
_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)+(0.1331P)²+32.8703P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2834
_refine_ls_wR_factor_ref         0.2886
_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. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.b X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_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
Ag1 Ag 0.7856(4) 0.63268(14) 0.53521(10) 0.0357(7) Uani 1 1 d . . . . .
O1 O 0.642(3) 0.7150(13) 0.1241(10) 0.035(3) Uani 1 1 d . . . . .
N4 N 0.448(3) 0.5342(12) 0.2272(10) 0.019(3) Uani 1 1 d . U . . .
N1 N 0.622(3) 0.5568(13) 0.3848(10) 0.022(3) Uani 1 1 d . . . . .
N3 N 0.688(4) 0.4530(14) 0.2574(11) 0.028(3) Uani 1 1 d . . . . .
N2 N 0.792(3) 0.4676(13) 0.3526(11) 0.023(3) Uani 1 1 d . . . . .
O2 O 0.230(3) 0.6864(14) -0.0084(11) 0.041(3) Uani 1 1 d . U . . .
N5 N 0.191(4) 0.6860(15) 0.3026(12) 0.031(3) Uani 1 1 d . . . . .
H5A H 0.1849 0.7218 0.3566 0.037 Uiso 1 1 calc R . . . .
H5B H 0.0580 0.7074 0.2474 0.037 Uiso 1 1 calc R . . . .
C1 C 0.403(4) 0.5988(16) 0.3046(12) 0.022(4) Uani 1 1 d . . . . .
C3 C 0.392(4) 0.6607(17) 0.0758(12) 0.023(4) Uani 1 1 d . . . . .
C2 C 0.282(4) 0.5489(16) 0.1225(12) 0.022(4) Uani 1 1 d . . . . .
H2A H 0.0499 0.5553 0.1150 0.026 Uiso 1 1 calc R . . . .
H2B H 0.3179 0.4765 0.0872 0.026 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ag1 0.0488(11) 0.0345(10) 0.0186(9) -0.0053(6) 0.0003(6) 0.0124(7)
O1 0.021(6) 0.040(8) 0.038(8) 0.009(6) -0.002(6) -0.011(6)
N4 0.025(6) 0.020(6) 0.010(6) 0.002(5) -0.001(5) -0.001(5)
N1 0.031(8) 0.020(7) 0.016(7) 0.000(6) 0.009(6) -0.002(6)
N3 0.028(8) 0.027(8) 0.026(9) 0.001(6) -0.001(6) 0.008(6)
N2 0.023(8) 0.018(7) 0.027(8) -0.003(6) 0.005(6) 0.001(6)
O2 0.041(4) 0.041(4) 0.039(4) 0.002(2) 0.010(2) -0.001(2)
N5 0.033(9) 0.031(8) 0.028(8) -0.003(7) 0.007(7) 0.005(7)
C1 0.028(9) 0.021(8) 0.018(8) 0.004(7) 0.007(7) 0.000(7)
C3 0.027(9) 0.030(9) 0.013(8) 0.008(7) 0.008(7) 0.010(7)
C2 0.017(8) 0.027(9) 0.016(8) 0.003(7) -0.004(6) 0.007(7)

_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
Ag1 O1 2.265(13) 4_576 ?
Ag1 N1 2.200(14) . ?
Ag1 N2 2.322(14) 3_766 ?
O1 Ag1 2.265(13) 4_575 ?
O1 C3 1.25(2) . ?
N4 N3 1.34(2) . ?
N4 C1 1.36(2) . ?
N4 C2 1.46(2) . ?
N1 N2 1.37(2) . ?
N1 C1 1.34(2) . ?
N3 N2 1.30(2) . ?
N2 Ag1 2.322(14) 3_766 ?
O2 C3 1.23(2) . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N5 C1 1.31(2) . ?
C3 C2 1.52(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 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
O1 Ag1 N2 104.5(5) 4_576 3_766 ?
N1 Ag1 O1 138.1(5) . 4_576 ?
N1 Ag1 N2 117.3(5) . 3_766 ?
C3 O1 Ag1 111.7(11) . 4_575 ?
N3 N4 C1 110.9(13) . . ?
N3 N4 C2 121.1(14) . . ?
C1 N4 C2 127.9(14) . . ?
N2 N1 Ag1 121.9(10) . . ?
C1 N1 Ag1 130.3(12) . . ?
C1 N1 N2 106.4(13) . . ?
N2 N3 N4 105.2(14) . . ?
N1 N2 Ag1 119.9(10) . 3_766 ?
N3 N2 Ag1 128.6(11) . 3_766 ?
N3 N2 N1 111.4(13) . . ?
H5A N5 H5B 120.0 . . ?
C1 N5 H5A 120.0 . . ?
C1 N5 H5B 120.0 . . ?
N1 C1 N4 106.0(14) . . ?
N5 C1 N4 127.8(16) . . ?
N5 C1 N1 126.2(16) . . ?
O1 C3 C2 117.9(14) . . ?
O2 C3 O1 126.1(17) . . ?
O2 C3 C2 116.0(16) . . ?
N4 C2 C3 113.5(14) . . ?
N4 C2 H2A 108.9 . . ?
N4 C2 H2B 108.9 . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?

_shelx_res_file                  
;
    22qq.res created by SHELXL-2014/7

TITL 22qq_a.res in P2(1)/c
REM Old TITL 22qq_a.res in P2(1)/n New: P21/c
REM SHELXT solution in P2(1)/c
REM R1 0.205, Rweak 0.067, Alpha 0.089, Orientation as input
REM Formula found by SHELXT: C8 Br O2
CELL 0.71073 4.2779 10.937 14.054 90 105.837 90
ZERR 4 0.0009 0.002 0.003 0 0.008 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Ag N O
UNIT 12 16 4 20 8
ISOR 0.01 0.02 N4
ISOR 0.001 0.002 O2

L.S. 5
PLAN  -20
SIZE 0.19 0.18 0.17
BOND $H
list 4
fmap 2
acta
OMIT -3 50.02
REM <olex2.extras>
REM <HklSrc "%.\\22qq.hkl">
REM </olex2.extras>

WGHT    0.133100   32.870300
FVAR       0.54462
AG1   3    0.785614    0.632682    0.535210    11.00000    0.04882    0.03453 =
         0.01859   -0.00530    0.00029    0.01238
O1    5    0.642101    0.714998    0.124102    11.00000    0.02132    0.04034 =
         0.03798    0.00912   -0.00183   -0.01093
N4    4    0.448500    0.534245    0.227164    11.00000    0.02459    0.02034 =
         0.00990    0.00222   -0.00134   -0.00081
N1    4    0.621950    0.556786    0.384805    11.00000    0.03089    0.01993 =
         0.01607    0.00043    0.00946   -0.00237
N3    4    0.688492    0.452976    0.257442    11.00000    0.02756    0.02676 =
         0.02606    0.00093   -0.00060    0.00774
N2    4    0.792405    0.467650    0.352649    11.00000    0.02250    0.01832 =
         0.02729   -0.00316    0.00492    0.00135
O2    5    0.229787    0.686354   -0.008371    11.00000    0.04131    0.04105 =
         0.03879    0.00162    0.00950   -0.00107
N5    4    0.190954    0.685977    0.302636    11.00000    0.03317    0.03057 =
         0.02750   -0.00286    0.00716    0.00513
AFIX  93
H5A   2    0.184889    0.721819    0.356569    11.00000   -1.20000
H5B   2    0.058038    0.707359    0.247406    11.00000   -1.20000
AFIX   0
C1    1    0.402692    0.598798    0.304612    11.00000    0.02795    0.02078 =
         0.01815    0.00402    0.00723    0.00035
C3    1    0.392081    0.660741    0.075789    11.00000    0.02652    0.03020 =
         0.01298    0.00768    0.00849    0.01042
C2    1    0.281549    0.548932    0.122539    11.00000    0.01701    0.02742 =
         0.01556    0.00253   -0.00430    0.00663
AFIX  23
H2A   2    0.049866    0.555291    0.114966    11.00000   -1.20000
H2B   2    0.317910    0.476462    0.087223    11.00000   -1.20000
AFIX   0
HKLF 4

REM  22qq_a.res in P2(1)/c
REM R1 =  0.1073 for     978 Fo > 4sig(Fo)  and  0.1143 for all    1113 data
REM    100 parameters refined using     12 restraints

END

WGHT      0.1330     32.8703

REM Highest difference peak  5.886,  deepest hole -1.346,  1-sigma level  0.437
Q1    1   0.5426  0.6350  0.5317  11.00000  0.05    5.89
Q2    1   1.0451  0.6325  0.5381  11.00000  0.05    5.64
Q3    1   0.3002  0.6329  0.5352  11.00000  0.05    3.26
Q4    1   1.1295  0.7839  0.6289  11.00000  0.05    1.32
Q5    1   1.0496  0.8030  0.4965  11.00000  0.05    1.18
Q6    1   0.9133  0.7901  0.6202  11.00000  0.05    1.14
Q7    1   0.4416  0.5332  0.6475  11.00000  0.05    1.11
Q8    1   0.3707  0.6505 -0.0217  11.00000  0.05    1.09
Q9    1   0.4553  0.8222  0.4888  11.00000  0.05    1.07
Q10   1  -0.0783  0.6867  0.2997  11.00000  0.05    0.99
Q11   1   0.4585  0.4527  0.2573  11.00000  0.05    0.96
Q12   1   0.6781  0.5274  0.6486  11.00000  0.05    0.93
Q13   1   0.5026  0.5426  0.1228  11.00000  0.05    0.92
Q14   1   0.6752  0.5369  0.2222  11.00000  0.05    0.89
Q15   1   0.0799  0.5826  0.1220  11.00000  0.05    0.84
Q16   1   0.1983  0.4482  0.2604  11.00000  0.05    0.84
Q17   1   0.7184  0.6937  0.3019  11.00000  0.05    0.83
Q18   1   0.4322  0.7194  0.1209  11.00000  0.05    0.80
Q19   1   0.2493  0.5330  0.2309  11.00000  0.05    0.80
Q20   1   0.8929  0.5395  0.3905  11.00000  0.05    0.75
;
_shelx_res_checksum              4828
_olex2_submission_special_instructions 'No special instructions were received'
