# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_cu_ak_ok2_rycek
_database_code_depnum_ccdc_archive 'CCDC 2348298'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;

_audit_update_record             
;
2024-06-10 deposited with the CCDC.	2024-06-20 downloaded from the CCDC.
;
_publcif_datablock.id            {2c181661-6744-4dc2-84da-e648bb9b1ba6}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 Ag Br N2 O'
_chemical_formula_sum            'C11 H11 Ag Br N2 O'
_chemical_formula_weight         375.00
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.1306 4.2820 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3550(11)
_cell_length_b                   4.2932(3)
_cell_length_c                   18.9380(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.204(5)
_cell_angle_gamma                90
_cell_volume                     1163.91(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2058
_cell_measurement_theta_min      3.0870
_cell_measurement_theta_max      66.5807

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.140
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.019
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    17.749
_shelx_estimated_absorpt_T_min   0.085
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.78
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7588
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_av_R_equivalents  0.0929
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         66.915
_diffrn_reflns_theta_full        66.915
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2045
_reflns_number_gt                1339
_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 Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury [DOI: 10.1107/S1600576719014092]'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0432P)²+24.9033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
Ag1 Ag 0.45282(6) 0.1009(3) 0.66633(5) 0.0363(3) Uani 1 1 d . . . . .
Br1 Br 0.42017(8) 0.0999(4) 0.79848(6) 0.0308(4) Uani 1 1 d . . . . .
N1 N 0.2683(7) 0.240(3) 0.5220(5) 0.033(3) Uani 1 1 d . . . . .
N2 N 0.3728(7) 0.036(3) 0.4882(5) 0.032(3) Uani 1 1 d . . . . .
O1 O 0.0618(6) 0.685(2) 0.6898(5) 0.042(3) Uani 1 1 d . . . . .
C1 C 0.2155(8) 0.357(3) 0.5665(6) 0.031(3) Uani 1 1 d . . . . .
C2 C 0.2594(9) 0.540(3) 0.6277(7) 0.033(3) Uani 1 1 d . . . . .
H2 H 0.323594 0.589943 0.640630 0.040 Uiso 1 1 calc R U . . .
C3 C 0.2106(8) 0.653(3) 0.6714(6) 0.032(3) Uani 1 1 d . . . . .
H3 H 0.240765 0.780063 0.714351 0.038 Uiso 1 1 calc R U . . .
C4 C 0.1172(8) 0.577(3) 0.6509(7) 0.033(3) Uani 1 1 d . . . . .
C5 C 0.0731(8) 0.385(4) 0.5897(6) 0.037(3) Uani 1 1 d . . . . .
H5 H 0.009253 0.330082 0.576786 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1239(8) 0.273(4) 0.5472(7) 0.034(3) Uani 1 1 d . . . . .
H6 H 0.095241 0.138723 0.505247 0.041 Uiso 1 1 calc R U . . .
C7 C 0.3561(8) 0.125(3) 0.5504(6) 0.026(3) Uani 1 1 d . . . . .
C8 C 0.2313(9) 0.223(4) 0.4428(7) 0.039(4) Uani 1 1 d . . . . .
H8 H 0.170864 0.285093 0.410026 0.047 Uiso 1 1 calc R U . . .
C9 C 0.3003(9) 0.098(4) 0.4231(7) 0.039(3) Uani 1 1 d . . . . .
H9 H 0.298170 0.060493 0.373030 0.046 Uiso 1 1 calc R U . . .
C10 C 0.4609(8) -0.124(3) 0.4941(6) 0.027(3) Uani 1 1 d . . . . .
H10A H 0.451429 -0.243540 0.447205 0.033 Uiso 1 1 calc R U . . .
H10B H 0.479435 -0.270852 0.537221 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1070(10) 0.858(4) 0.7575(7) 0.048(4) Uani 1 1 d . . . . .
H11A H 0.154889 0.727561 0.793807 0.071 Uiso 1 1 calc R U . . .
H11B H 0.060834 0.920449 0.779414 0.071 Uiso 1 1 calc R U . . .
H11C H 0.136242 1.043361 0.745713 0.071 Uiso 1 1 calc R 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
Ag1 C7 2.163(11) . ?
Ag1 Br1 2.7243(13) . ?
Ag1 Br1 2.810(2) 2_656 ?
Ag1 Br1 2.816(2) 2_646 ?
N1 C7 1.351(15) . ?
N1 C8 1.400(14) . ?
N1 C1 1.454(15) . ?
N2 C7 1.349(14) . ?
N2 C9 1.356(15) . ?
N2 C10 1.485(15) . ?
O1 C4 1.391(14) . ?
O1 C11 1.425(15) . ?
C1 C2 1.359(17) . ?
C1 C6 1.368(17) . ?
C2 C3 1.390(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(18) . ?
C5 C6 1.393(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C9 1.354(18) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C10 1.56(2) 3_656 ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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
C7 Ag1 Br1 130.2(3) . . ?
C7 Ag1 Br1 111.5(3) . 2_656 ?
Br1 Ag1 Br1 97.22(5) . 2_656 ?
C7 Ag1 Br1 116.1(4) . 2_646 ?
Br1 Ag1 Br1 97.08(5) . 2_646 ?
Br1 Ag1 Br1 99.46(5) 2_656 2_646 ?
Ag1 Br1 Ag1 82.90(5) . 2_646 ?
Ag1 Br1 Ag1 82.79(5) . 2_656 ?
Ag1 Br1 Ag1 99.46(5) 2_646 2_656 ?
C7 N1 C8 111.5(10) . . ?
C7 N1 C1 125.5(9) . . ?
C8 N1 C1 123.0(10) . . ?
C7 N2 C9 112.8(10) . . ?
C7 N2 C10 121.4(9) . . ?
C9 N2 C10 125.8(10) . . ?
C4 O1 C11 117.2(10) . . ?
C2 C1 C6 121.7(11) . . ?
C2 C1 N1 119.0(11) . . ?
C6 C1 N1 119.2(11) . . ?
C1 C2 C3 120.1(11) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 118.6(12) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 121.2(11) . . ?
C3 C4 O1 123.0(12) . . ?
C5 C4 O1 115.8(11) . . ?
C4 C5 C6 118.9(11) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 119.4(12) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N2 C7 N1 103.5(9) . . ?
N2 C7 Ag1 126.5(8) . . ?
N1 C7 Ag1 130.0(8) . . ?
C9 C8 N1 105.2(11) . . ?
C9 C8 H8 127.4 . . ?
N1 C8 H8 127.4 . . ?
C8 C9 N2 107.0(10) . . ?
C8 C9 H9 126.5 . . ?
N2 C9 H9 126.5 . . ?
N2 C10 C10 109.3(13) . 3_656 ?
N2 C10 H10A 109.8 . . ?
C10 C10 H10A 109.8 3_656 . ?
N2 C10 H10B 109.8 . . ?
C10 C10 H10B 109.8 3_656 . ?
H10A C10 H10B 108.3 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_refine_diff_density_max         1.635
_refine_diff_density_min         -1.612
_refine_diff_density_rms         0.211



loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
