#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:14:18 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/24/7232454.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_7232454
loop_
_publ_author_name
'Baudron, Stéphane A.'
'Chevreau, Hubert'
_publ_section_title
;
 Revisiting Ag--π interactions with bis((pyrrol-2-yl)methylene)hydrazine:
 CC versus CN bond complexation
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              1853
_journal_paper_doi               10.1039/C9CE00168A
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C12 H14 Ag2 F6 N4 O8 S2'
_chemical_formula_weight         736.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-01-27 deposited with the CCDC.    2019-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                63.173(2)
_cell_angle_beta                 82.885(2)
_cell_angle_gamma                89.971(2)
_cell_formula_units_Z            1
_cell_length_a                   6.1112(3)
_cell_length_b                   9.5660(5)
_cell_length_c                   10.6221(6)
_cell_measurement_reflns_used    9755
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.87
_cell_measurement_theta_min      2.39
_cell_volume                     548.79(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            50377
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.155
_diffrn_reflns_theta_min         2.169
_exptl_absorpt_coefficient_mu    2.073
_exptl_absorpt_correction_T_max  0.959
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    2.227
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             358
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0204
_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)+(0.0278P)²+0.1003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0477
_refine_ls_wR_factor_ref         0.0480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2914
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00168a2.cif
_cod_data_source_block           compound3
_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 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7232452--7232457.cif.
;
_cod_database_code               7232454
_shelx_shelxl_version_number     2016/6
_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   0.922
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 1.1147(4) 0.8093(3) 0.7972(3) 0.0337(5) Uani 1 1 d . .
H1 H 1.211990 0.726519 0.829223 0.040 Uiso 1 1 calc R U
C2 C 1.1093(4) 0.9338(3) 0.8289(3) 0.0338(5) Uani 1 1 d . .
H2 H 1.202401 0.953218 0.885317 0.041 Uiso 1 1 calc R U
C3 C 0.9405(4) 1.0267(3) 0.7622(2) 0.0282(4) Uani 1 1 d . .
H3 H 0.897068 1.120261 0.765820 0.034 Uiso 1 1 calc R U
C4 C 0.8487(3) 0.9566(3) 0.6898(2) 0.0244(4) Uani 1 1 d . .
C5 C 0.6698(3) 1.0148(2) 0.6085(2) 0.0240(4) Uani 1 1 d . .
H5 H 0.601470 1.102214 0.612428 0.029 Uiso 1 1 calc R U
C6 C 0.5495(6) 0.6550(5) 0.1040(3) 0.0543(8) Uani 1 1 d . .
N1 N 0.5922(3) 0.9612(2) 0.53093(17) 0.0219(3) Uani 1 1 d . .
N2 N 0.9579(3) 0.8242(2) 0.7128(2) 0.0276(3) Uani 1 1 d . .
H2A H 0.930749 0.758872 0.678261 0.033 Uiso 1 1 calc R U
O1 O 0.7168(3) 0.6762(3) 0.3034(2) 0.0439(4) Uani 1 1 d . .
O2 O 0.3173(3) 0.6454(2) 0.3271(2) 0.0377(4) Uani 1 1 d . .
O3 O 0.5419(3) 0.4279(2) 0.3546(2) 0.0428(5) Uani 1 1 d . .
O4 O 0.9874(3) 0.6101(2) 0.5945(2) 0.0342(4) Uani 1 1 d D .
S1 S 0.52799(8) 0.59453(6) 0.29290(5) 0.02327(9) Uani 1 1 d . .
F1 F 0.3803(5) 0.5940(5) 0.0762(3) 0.1045(12) Uani 1 1 d . .
F2 F 0.7339(4) 0.6110(4) 0.0582(2) 0.0805(8) Uani 1 1 d . .
F3 F 0.5454(6) 0.8087(4) 0.0327(3) 0.1070(12) Uani 1 1 d . .
Ag1 Ag 0.76044(3) 0.80210(2) 0.44635(2) 0.03019(5) Uani 1 1 d . .
H4A H 0.914(5) 0.521(2) 0.640(4) 0.059(11) Uiso 1 1 d D .
H4B H 1.127(2) 0.617(5) 0.572(6) 0.11(2) Uiso 1 1 d D .
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'
F F 0.0171 0.0103 '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'
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
N2 C1 C2 108.7(2) . .
N2 C1 H1 125.7 . .
C2 C1 H1 125.7 . .
C1 C2 C3 107.1(2) . .
C1 C2 H2 126.5 . .
C3 C2 H2 126.5 . .
C4 C3 C2 107.4(2) . .
C4 C3 Ag1 95.45(13) . 2_776
C2 C3 Ag1 87.64(15) . 2_776
C4 C3 H3 126.3 . .
C2 C3 H3 126.3 . .
Ag1 C3 H3 87.4 2_776 .
N2 C4 C3 107.51(18) . .
N2 C4 C5 127.6(2) . .
C3 C4 C5 124.9(2) . .
N1 C5 C4 126.78(19) . .
N1 C5 H5 116.6 . .
C4 C5 H5 116.6 . .
F1 C6 F2 109.3(3) . .
F1 C6 F3 107.1(3) . .
F2 C6 F3 108.9(3) . .
F1 C6 S1 110.2(2) . .
F2 C6 S1 110.9(2) . .
F3 C6 S1 110.4(3) . .
C5 N1 N1 113.6(2) . 2_676
C5 N1 Ag1 126.92(13) . .
N1 N1 Ag1 117.91(17) 2_676 .
C1 N2 C4 109.3(2) . .
C1 N2 H2A 125.3 . .
C4 N2 H2A 125.3 . .
S1 O1 Ag1 131.19(11) . .
Ag1 O4 H4A 110(3) . .
Ag1 O4 H4B 121(3) . .
H4A O4 H4B 121.5(19) . .
O3 S1 O1 113.77(13) . .
O3 S1 O2 114.83(11) . .
O1 S1 O2 115.13(12) . .
O3 S1 C6 103.93(17) . .
O1 S1 C6 102.98(15) . .
O2 S1 C6 104.18(14) . .
N1 Ag1 O1 142.91(7) . .
N1 Ag1 O4 117.56(6) . .
O1 Ag1 O4 94.66(7) . .
N1 Ag1 C3 107.30(7) . 2_776
O1 Ag1 C3 83.29(7) . 2_776
O4 Ag1 C3 99.21(7) . 2_776
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.356(3) .
C1 C2 1.375(4) .
C1 H1 0.9500 .
C2 C3 1.403(3) .
C2 H2 0.9500 .
C3 C4 1.389(3) .
C3 Ag1 2.580(2) 2_776
C3 H3 0.9500 .
C4 N2 1.367(3) .
C4 C5 1.432(3) .
C5 N1 1.283(3) .
C5 H5 0.9500 .
C6 F1 1.315(5) .
C6 F2 1.316(4) .
C6 F3 1.317(5) .
C6 S1 1.807(3) .
N1 N1 1.412(3) 2_676
N1 Ag1 2.2769(17) .
N2 H2A 0.8800 .
O1 S1 1.4369(19) .
O1 Ag1 2.3621(19) .
O2 S1 1.4390(16) .
O3 S1 1.4311(19) .
O4 Ag1 2.3885(17) .
O4 H4A 0.857(9) .
O4 H4B 0.850(10) .
