#------------------------------------------------------------------------------
#$Date: 2017-03-04 15:14:04 +0200 (Sat, 04 Mar 2017) $
#$Revision: 193432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/51/4345177.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4345177
loop_
_publ_author_name
'Liu, Guang-Ning'
'Jiang, Xiao-Ming'
'Fan, Qing-Shun'
'Hussain, Muhammad Bilal'
'Li, Ke'
'Sun, Hui'
'Li, Xin-Yu'
'Liu, Wan-Qing'
'Li, Cuncheng'
_publ_section_title
;
 Water Stability Studies of Hybrid Iodoargentates Containing N-Alkylated
 or N-Protonated Structure Directing Agents: Exploring Noncentrosymmetric
 Hybrid Structures.
;
_journal_issue                   4
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1906
_journal_page_last               1918
_journal_paper_doi               10.1021/acs.inorgchem.6b02478
_journal_volume                  56
_journal_year                    2017
_chemical_formula_sum            'C9 H10 Ag I2 N S'
_chemical_formula_weight         525.91
_space_group_crystal_system      orthorhombic
_space_group_IT_number           26
_space_group_name_Hall           'P 2c -2'
_space_group_name_H-M_alt        'P m c 21'
_symmetry_space_group_name_Hall  'P 2c -2'
_symmetry_space_group_name_H-M   'P m c 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8601(2)
_cell_length_b                   10.0648(4)
_cell_length_c                   18.7786(6)
_cell_measurement_reflns_used    4173
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0010
_cell_measurement_theta_min      3.7290
_cell_volume                     1296.58(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0355
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13052
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.359
_diffrn_reflns_theta_min         3.594
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.442
_exptl_absorpt_correction_T_max  0.2852
_exptl_absorpt_correction_T_min  0.2323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;                                                         
CrysAlisPro, Agilent Technologies,                        
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46)                           
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.         
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.801
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0409P)²+1.6982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2505
_reflns_number_total             2847
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b02478_si_001.cif
_cod_data_source_block           compound_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4345177--4345180.cif.
;
_cod_original_cell_volume        1296.57(8)
_cod_database_code               4345177
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.232
_shelx_estimated_absorpt_t_max   0.285
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z'
'x, -y, z+1/2'
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
Ag1 Ag 0.25326(4) 0.43334(4) 0.32345(2) 0.06628(9) Uani 1 1 d . . .
I1 I 0.0000 0.35479(4) 0.43642(2) 0.06012(10) Uani 1 2 d S T P
I2 I 0.0000 0.55519(4) 0.21980(2) 0.05876(10) Uani 1 2 d S T P
I3 I 0.5000 0.22158(4) 0.28306(2) 0.05782(9) Uani 1 2 d S T P
I4 I 0.5000 0.64639(3) 0.37561(2) 0.05023(8) Uani 1 2 d S T P
S1 S 0.0000 0.35259(16) 0.03736(9) 0.0713(5) Uani 1 2 d S T P
S2 S 0.5000 0.85252(13) 0.20471(5) 0.0497(3) Uani 1 2 d S T P
N1 N 0.0000 0.1524(6) -0.0426(3) 0.089(2) Uani 1 2 d S T P
N2 N 0.5000 0.6880(4) 0.10355(18) 0.0381(10) Uani 1 2 d S T P
C1 C 0.0000 0.1117(13) -0.1670(4) 0.375(13) Uani 1 2 d DS T P
H1B H 0.0000 0.2054 -0.1617 0.562 Uiso 1 2 d R U P
H1A H -0.1127 0.0856 -0.1927 0.562 Uiso 1 1 d R U .
C2 C 0.0000 0.0496(8) -0.0979(3) 0.134(3) Uani 1 2 d DS T P
H2B H 0.1145 -0.0062 -0.0929 0.201 Uiso 1 1 d R U .
C3 C 0.0000 0.2815(6) -0.0435(3) 0.0714(19) Uani 1 2 d S T P
H3 H 0.0000 0.3305 -0.0855 0.086 Uiso 1 2 calc R U P
C4 C 0.0000 0.0941(6) 0.0245(3) 0.0647(18) Uani 1 2 d S T P
C5 C 0.0000 -0.0380(6) 0.0443(3) 0.071(2) Uani 1 2 d S T P
H5 H 0.0000 -0.1059 0.0108 0.085 Uiso 1 2 calc R U P
C6 C 0.0000 -0.0617(10) 0.1100(4) 0.110(2) Uani 1 2 d S TU P
H6 H 0.0000 -0.1513 0.1222 0.132 Uiso 1 2 calc R U P
C7 C 0.0000 0.0188(11) 0.1622(4) 0.134(3) Uani 1 2 d S T P
H7 H 0.0000 -0.0120 0.2089 0.161 Uiso 1 2 calc R U P
C8 C 0.0000 0.1586(9) 0.1468(4) 0.094(3) Uani 1 2 d S T P
H8 H 0.0000 0.2212 0.1832 0.113 Uiso 1 2 calc R U P
C9 C 0.0000 0.1975(6) 0.0756(4) 0.0664(18) Uani 1 2 d S T P
C10 C 0.5000 0.4389(5) 0.1052(3) 0.0572(16) Uani 1 2 d S T P
H10B H 0.5000 0.3647 0.0746 0.086 Uiso 1 2 d R U P
H10A H 0.6119 0.4357 0.1343 0.086 Uiso 1 1 d R U .
C11 C 0.5000 0.5658(5) 0.0618(3) 0.0541(15) Uani 1 2 d S T P
H11B H 0.6140 0.5658 0.0313 0.065 Uiso 0.5 1 calc R U P
H11A H 0.3860 0.5658 0.0313 0.065 Uiso 0.5 1 calc R U P
C12 C 0.5000 0.6968(6) 0.1712(2) 0.0482(14) Uani 1 2 d S T P
H12 H 0.5000 0.6221 0.2004 0.058 Uiso 1 2 calc R U P
C13 C 0.5000 0.9165(5) 0.1190(2) 0.0433(13) Uani 1 2 d S T P
C14 C 0.5000 1.0458(5) 0.0953(2) 0.0482(13) Uani 1 2 d S T P
H14 H 0.5000 1.1165 0.1272 0.058 Uiso 1 2 calc R U P
C15 C 0.5000 1.0666(5) 0.0249(3) 0.0554(16) Uani 1 2 d S T P
H15 H 0.5000 1.1536 0.0082 0.066 Uiso 1 2 calc R U P
C16 C 0.5000 0.9641(6) -0.0236(2) 0.0522(16) Uani 1 2 d S T P
H16 H 0.5000 0.9844 -0.0719 0.063 Uiso 1 2 calc R U P
C17 C 0.5000 0.8341(5) -0.0037(2) 0.0491(14) Uani 1 2 d S T P
H17 H 0.5000 0.7654 -0.0368 0.059 Uiso 1 2 calc R U P
C18 C 0.5000 0.8106(5) 0.0685(2) 0.0368(11) Uani 1 2 d S T P
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'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
I3 Ag1 I1 110.809(15) . .
I3 Ag1 I2 120.048(15) . .
I1 Ag1 I2 104.646(12) . .
I3 Ag1 I4 107.371(12) . .
I1 Ag1 I4 107.990(14) . .
I2 Ag1 I4 105.373(14) . .
Ag1 I1 Ag1 75.005(15) 3 .
Ag1 I2 Ag1 74.122(15) . 3
Ag1 I3 Ag1 73.608(16) . 3_655
Ag1 I4 Ag1 71.358(15) . 3_655
C3 S1 C9 89.5(3) . .
C12 S2 C13 90.0(2) . .
C3 N1 C4 115.7(6) . .
C3 N1 C2 134.2(6) . .
C4 N1 C2 110.1(5) . .
C12 N2 C18 114.1(4) . .
C12 N2 C11 126.5(4) . .
C18 N2 C11 119.4(3) . .
C2 C1 H1B 109.7 . .
C2 C1 H1A 109.8 . .
H1B C1 H1A 109.2 . .
C1 C2 N1 109.4(7) . .
C1 C2 H2B 109.8 . .
N1 C2 H2B 109.8 . .
N1 C3 S1 114.5(5) . .
N1 C3 H3 122.8 . .
S1 C3 H3 122.8 . .
C5 C4 N1 130.6(6) . .
C5 C4 C9 121.8(6) . .
N1 C4 C9 107.6(6) . .
C6 C5 C4 116.6(7) . .
C6 C5 H5 121.7 . .
C4 C5 H5 121.7 . .
C5 C6 C7 129.5(10) . .
C5 C6 H6 115.3 . .
C7 C6 H6 115.3 . .
C6 C7 C8 117.9(8) . .
C6 C7 H7 121.0 . .
C8 C7 H7 121.0 . .
C9 C8 C7 117.9(7) . .
C9 C8 H8 121.0 . .
C7 C8 H8 121.0 . .
C8 C9 C4 116.3(6) . .
C8 C9 S1 131.0(6) . .
C4 C9 S1 112.7(5) . .
C11 C10 H10B 109.8 . .
C11 C10 H10A 109.9 . .
H10B C10 H10A 109.1 . .
N2 C11 C10 115.0(4) . .
N2 C11 H11B 108.5 . .
C10 C11 H11B 108.5 . .
N2 C11 H11A 108.5 . .
C10 C11 H11A 108.5 . .
H11B C11 H11A 107.5 . .
N2 C12 S2 115.8(4) . .
N2 C12 H12 122.1 . .
S2 C12 H12 122.1 . .
C14 C13 C18 119.4(4) . .
C14 C13 S2 130.8(4) . .
C18 C13 S2 109.8(3) . .
C15 C14 C13 117.9(4) . .
C15 C14 H14 121.0 . .
C13 C14 H14 121.0 . .
C14 C15 C16 122.4(5) . .
C14 C15 H15 118.8 . .
C16 C15 H15 118.8 . .
C17 C16 C15 122.6(4) . .
C17 C16 H16 118.7 . .
C15 C16 H16 118.7 . .
C16 C17 C18 115.9(4) . .
C16 C17 H17 122.1 . .
C18 C17 H17 122.1 . .
C17 C18 N2 128.0(4) . .
C17 C18 C13 121.7(4) . .
N2 C18 C13 110.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 I3 2.8254(4) .
Ag1 I1 2.8538(4) .
Ag1 I2 2.8828(4) .
Ag1 I4 2.9021(4) .
I1 Ag1 2.8537(4) 3
I2 Ag1 2.8828(4) 3
I3 Ag1 2.8254(4) 3_655
I4 Ag1 2.9021(4) 3_655
S1 C3 1.679(6) .
S1 C9 1.718(7) .
S2 C12 1.689(6) .
S2 C13 1.733(4) .
N1 C3 1.299(8) .
N1 C4 1.391(8) .
N1 C2 1.467(9) .
N2 C12 1.274(5) .
N2 C18 1.398(6) .
N2 C11 1.459(6) .
C1 C2 1.440(11) .
C1 H1B 0.9481 .
C1 H1A 0.9482 .
C2 H2B 0.9700 .
C3 H3 0.9300 .
C4 C5 1.380(8) .
C4 C9 1.415(9) .
C5 C6 1.255(10) .
C5 H5 0.9300 .
C6 C7 1.272(13) .
C6 H6 0.9300 .
C7 C8 1.437(14) .
C7 H7 0.9300 .
C8 C9 1.394(10) .
C8 H8 0.9300 .
C10 C11 1.515(7) .
C10 H10B 0.9422 .
C10 H10A 0.9422 .
C11 H11B 0.9700 .
C11 H11A 0.9700 .
C12 H12 0.9300 .
C13 C14 1.375(7) .
C13 C18 1.427(6) .
C14 C15 1.338(7) .
C14 H14 0.9300 .
C15 C16 1.377(7) .
C15 H15 0.9300 .
C16 C17 1.360(8) .
C16 H16 0.9300 .
C17 C18 1.377(6) .
C17 H17 0.9300 .
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
C3 N1 C2 C1 0.000(1)
C4 N1 C2 C1 180.000(0)
C4 N1 C3 S1 0.000(0)
C2 N1 C3 S1 180.000(0)
C9 S1 C3 N1 0.000(0)
C3 N1 C4 C5 180.000(0)
C2 N1 C4 C5 0.000(0)
C3 N1 C4 C9 0.000(0)
C2 N1 C4 C9 180.000(0)
N1 C4 C5 C6 180.000(0)
C9 C4 C5 C6 0.000(0)
C4 C5 C6 C7 0.000(1)
C5 C6 C7 C8 0.000(1)
C6 C7 C8 C9 0.000(1)
C7 C8 C9 C4 0.000(1)
C7 C8 C9 S1 180.000(1)
C5 C4 C9 C8 0.000(1)
N1 C4 C9 C8 180.000(1)
C5 C4 C9 S1 180.000(0)
N1 C4 C9 S1 0.000(0)
C3 S1 C9 C8 180.000(1)
C3 S1 C9 C4 0.000(0)
C12 N2 C11 C10 0.000(1)
C18 N2 C11 C10 180.000(1)
C18 N2 C12 S2 0.000(1)
C11 N2 C12 S2 180.000(1)
C13 S2 C12 N2 0.000(1)
C12 S2 C13 C14 180.000(1)
C12 S2 C13 C18 0.000(1)
C18 C13 C14 C15 0.000(2)
S2 C13 C14 C15 180.000(2)
C13 C14 C15 C16 0.000(2)
C14 C15 C16 C17 0.000(2)
C15 C16 C17 C18 0.000(2)
C16 C17 C18 N2 180.000(1)
C16 C17 C18 C13 0.000(1)
C12 N2 C18 C17 180.000(1)
C11 N2 C18 C17 0.000(1)
C12 N2 C18 C13 0.000(1)
C11 N2 C18 C13 180.000(1)
C14 C13 C18 C17 0.000(2)
S2 C13 C18 C17 180.000(1)
C14 C13 C18 N2 180.000(1)
S2 C13 C18 N2 0.000(1)
