#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:14:18 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223736 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/24/7232453.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_7232453
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            'C11 H14 Ag2 N6 O7'
_chemical_formula_weight         558.02
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.5483(12)
_cell_length_b                   16.1886(10)
_cell_length_c                   4.8655(2)
_cell_measurement_reflns_used    4101
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.21
_cell_measurement_theta_min      2.35
_cell_volume                     1618.50(15)
_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 0.993
_diffrn_measured_fraction_theta_max 0.969
_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  0.0343
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            10291
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.278
_diffrn_reflns_theta_min         2.348
_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.290
_exptl_crystal_density_meas      ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2414
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0250
_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)+(0.0226P)²+1.8825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2031
_reflns_number_total             2414
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ce00168a2.cif
_cod_data_source_block           compound6
_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               7232453
_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   0.790
_shelx_estimated_absorpt_t_max   0.908
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.67565(11) -0.04059(19) 0.2388(5) 0.0355(6) Uani 1 1 d . . . . .
H1 H 0.700298 -0.069721 0.105025 0.043 Uiso 1 1 calc R U . . .
C2 C 0.68407(11) 0.04057(19) 0.3096(5) 0.0359(6) Uani 1 1 d . . . . .
H2 H 0.714995 0.077672 0.233282 0.043 Uiso 1 1 calc R U . . .
C3 C 0.63807(11) 0.05892(16) 0.5178(5) 0.0268(5) Uani 1 1 d . . . . .
H3 H 0.632479 0.110476 0.607999 0.032 Uiso 1 1 calc R U . . .
C4 C 0.60263(10) -0.01297(15) 0.5648(4) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.54900(10) -0.03232(13) 0.7406(4) 0.0201(4) Uani 1 1 d . . . . .
H5 H 0.527581 -0.083700 0.713864 0.024 Uiso 1 1 calc R U . . .
N1 N 0.52780(8) 0.01533(11) 0.9329(4) 0.0182(3) Uani 1 1 d . . . . .
N2 N 0.62653(10) -0.07254(13) 0.3902(4) 0.0274(4) Uani 1 1 d . . . . .
H2A H 0.612073 -0.123594 0.378829 0.033 Uiso 1 1 calc R U . . .
N3 N 0.69811(14) 0.250000 -0.1190(7) 0.0340(7) Uani 1 2 d S T P . .
N4 N 0.51448(12) 0.250000 0.5468(5) 0.0190(5) Uani 1 2 d S T P . .
O1 O 0.63712(11) 0.250000 -0.0993(6) 0.0360(6) Uani 1 2 d S T P A .
O2 O 0.72937(16) 0.1868(2) -0.1255(11) 0.0875(15) Uani 0.738(5) 1 d . . P A 1
O2B O 0.7202(7) 0.250000 -0.374(4) 0.0875(15) Uani 0.262(5) 2 d S T P A 2
O2C O 0.7308(7) 0.250000 0.074(4) 0.0875(15) Uani 0.262(5) 2 d S T P A 2
O3 O 0.54006(15) 0.250000 0.3101(5) 0.0391(7) Uani 1 2 d S T P A .
O4 O 0.50212(8) 0.31717(10) 0.6574(3) 0.0259(3) Uani 1 1 d . . . . .
Ag1 Ag 0.58073(2) 0.12942(2) 0.09455(4) 0.02963(7) Uani 1 1 d . . . . .
O5 O 0.63771(11) 0.750000 0.2501(6) 0.0358(6) Uani 1 2 d DS T P . .
C6 C 0.6278(2) 0.750000 -0.0408(10) 0.0441(10) Uani 1 2 d S T P . .
H5A H 0.6775(8) 0.750000 0.294(10) 0.052(14) Uiso 1 2 d DS . P . .
H6A H 0.585(3) 0.750000 -0.089(11) 0.064(18) Uiso 1 2 d S . P . .
H6B H 0.6438(17) 0.796(2) -0.131(7) 0.053(10) Uiso 1 1 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'
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 108.9(2) . .
N2 C1 H1 125.5 . .
C2 C1 H1 125.5 . .
C1 C2 C3 107.3(2) . .
C1 C2 H2 126.4 . .
C3 C2 H2 126.4 . .
C4 C3 C2 106.9(2) . .
C4 C3 Ag1 104.90(14) . .
C2 C3 Ag1 80.23(15) . .
C4 C3 H3 126.5 . .
C2 C3 H3 126.5 . .
Ag1 C3 H3 85.8 . .
N2 C4 C3 107.3(2) . .
N2 C4 C5 119.4(2) . .
C3 C4 C5 133.2(2) . .
N1 C5 C4 124.3(2) . .
N1 C5 H5 117.8 . .
C4 C5 H5 117.8 . .
C5 N1 N1 113.6(2) . 5_657
C5 N1 Ag1 125.00(14) . 1_556
N1 N1 Ag1 120.82(17) 5_657 1_556
C1 N2 C4 109.6(2) . .
C1 N2 H2A 125.2 . .
C4 N2 H2A 125.2 . .
O2 N3 O2 115.7(4) 8_565 .
O2C N3 O1 121.2(9) . .
O2 N3 O1 122.1(2) 8_565 .
O2 N3 O1 122.1(2) . .
O2C N3 O2B 124.3(10) . .
O1 N3 O2B 114.5(7) . .
O4 N4 O4 122.6(3) . 8_565
O4 N4 O3 118.68(14) . .
O4 N4 O3 118.68(13) 8_565 .
N3 O1 Ag1 119.95(11) . 8_565
N3 O1 Ag1 119.95(11) . .
Ag1 O1 Ag1 105.15(9) 8_565 .
N4 O3 Ag1 123.33(6) . 8_565
N4 O3 Ag1 123.33(6) . .
Ag1 O3 Ag1 111.02(10) 8_565 .
N1 Ag1 O3 130.63(8) 1_554 .
N1 Ag1 O1 137.29(8) 1_554 .
O3 Ag1 O1 71.44(7) . .
N1 Ag1 C3 97.58(7) 1_554 .
O3 Ag1 C3 99.72(9) . .
O1 Ag1 C3 115.68(8) . .
C6 O5 H5A 113(3) . .
O5 C6 H6A 113(3) . .
O5 C6 H6B 115(2) . .
H6A C6 H6B 103(3) . .
O5 C6 H6B 115(2) . 8_575
H6A C6 H6B 103(3) . 8_575
H6B C6 H6B 108(4) . 8_575
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N2 1.352(3) .
C1 C2 1.369(4) .
C1 H1 0.9500 .
C2 C3 1.417(4) .
C2 H2 0.9500 .
C3 C4 1.392(3) .
C3 Ag1 2.633(2) .
C3 H3 0.9500 .
C4 N2 1.376(3) .
C4 C5 1.430(3) .
C5 N1 1.288(3) .
C5 H5 0.9500 .
N1 N1 1.407(3) 5_657
N1 Ag1 2.2832(18) 1_556
N2 H2A 0.8800 .
N3 O2C 1.15(2) .
N3 O2 1.208(4) 8_565
N3 O2 1.208(4) .
N3 O1 1.257(4) .
N3 O2B 1.32(2) .
N4 O4 1.239(2) .
N4 O4 1.239(2) 8_565
N4 O3 1.266(4) .
O1 Ag1 2.4579(15) 8_565
O1 Ag1 2.4580(15) .
O3 Ag1 2.3682(15) 8_565
O3 Ag1 2.3683(15) .
O5 C6 1.430(6) .
O5 H5A 0.845(10) .
C6 H6A 0.92(5) .
C6 H6B 0.93(4) .
C6 H6B 0.93(4) 8_575
