#------------------------------------------------------------------------------
#$Date: 2016-03-25 11:25:15 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179789 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/85/7008559.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_7008559
loop_
_publ_author_name
'Aakeröy, Christer B'
'Desper, John'
'Smith, Michelle M.'
'Urbina, Joaquin F.'
_publ_section_title
;
 [(Benzimidazol-1-yl)methyl]benzamides as bifunctional reagents for
 reliable inorganic-organic supramolecular synthesis.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2462
_journal_page_last               2470
_journal_paper_doi               10.1039/b504420k
_journal_year                    2005
_chemical_formula_moiety         '(C17 H17 N3 O)2 Ag (B F4)'
_chemical_formula_sum            'C34 H34 Ag B F4 N6 O2'
_chemical_formula_weight         753.35
_chemical_name_common
'bis(4-((6,7-dimethylbenzimidazol-1-yl)methyl)benzamide), AgBF4'
_chemical_name_systematic
;
bis{4-[(6,7-dimethylbenzimidazol-1-yl)methyl]benzamide}, AgBF4
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.108(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9140(7)
_cell_length_b                   8.4229(6)
_cell_length_c                   19.7055(13)
_cell_measurement_reflns_used    3914
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.40
_cell_volume                     1608.89(19)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_sigmaI/netI    0.0873
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11041
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.590
_refine_diff_density_min         -1.773
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1461
_reflns_number_gt                2685
_reflns_number_total             3711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b504420k.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2/n
_cod_database_code               7008559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.5000 0.5000 0.5000 0.03408(16) Uani 1 2 d S . .
B1 B 0.2870(10) 0.7327(11) 0.2515(5) 0.022(3) Uiso 0.271(11) 1 d PD A -1
F1 F 0.2642(13) 0.5735(9) 0.2616(6) 0.037(3) Uiso 0.271(11) 1 d PD A -1
F2 F 0.2427(13) 0.8292(15) 0.3002(5) 0.054(4) Uiso 0.271(11) 1 d PD A -1
F3 F 0.4257(11) 0.7587(12) 0.2535(7) 0.062(3) Uiso 0.271(11) 1 d PD A -1
F4 F 0.2062(12) 0.7770(9) 0.1857(3) 0.030(3) Uiso 0.271(11) 1 d PD A -1
B2 B 0.2564(14) 0.7173(15) 0.2438(6) 0.049(3) Uiso 0.229(11) 1 d PD A -2
F5 F 0.2686(18) 0.5569(13) 0.2580(9) 0.049(3) Uiso 0.229(11) 1 d PD A -2
F6 F 0.2298(15) 0.802(2) 0.3005(6) 0.049(3) Uiso 0.229(11) 1 d PD A -2
F7 F 0.3803(14) 0.7676(12) 0.2270(8) 0.049(3) Uiso 0.229(11) 1 d PD A -2
F8 F 0.1474(15) 0.7443(14) 0.1870(5) 0.049(3) Uiso 0.229(11) 1 d PD A -2
N10 N 0.0810(3) 0.4395(3) 0.40010(13) 0.0275(6) Uani 1 1 d . . .
C11 C 0.2121(4) 0.4892(4) 0.4064(2) 0.0327(8) Uani 1 1 d . . .
H11A H 0.2423 0.5546 0.3732 0.039 Uiso 1 1 calc R . .
N12 N 0.2936(3) 0.4374(4) 0.46342(15) 0.0321(6) Uani 1 1 d . . .
C13 C 0.2100(3) 0.3483(3) 0.49717(16) 0.0254(7) Uani 1 1 d . . .
C14 C 0.2429(4) 0.2646(4) 0.55902(17) 0.0293(7) Uani 1 1 d . . .
H14A H 0.3348 0.2630 0.5854 0.035 Uiso 1 1 calc R . .
C15 C 0.1399(4) 0.1842(4) 0.58136(17) 0.0289(7) Uani 1 1 d . . .
C16 C 0.0025(4) 0.1886(4) 0.54258(17) 0.0266(7) Uani 1 1 d . . .
C17 C -0.0301(4) 0.2717(4) 0.48039(18) 0.0263(7) Uani 1 1 d . . .
H17A H -0.1219 0.2753 0.4540 0.032 Uiso 1 1 calc R . .
C18 C 0.0763(3) 0.3494(3) 0.45816(16) 0.0248(7) Uani 1 1 d . . .
C19 C 0.1745(4) 0.0889(5) 0.6478(2) 0.0406(9) Uani 1 1 d . . .
H19A H 0.1727 -0.0246 0.6366 0.061 Uiso 1 1 calc R . .
H19B H 0.1066 0.1112 0.6761 0.061 Uiso 1 1 calc R . .
H19C H 0.2667 0.1181 0.6736 0.061 Uiso 1 1 calc R . .
C20 C -0.1105(4) 0.1035(4) 0.5675(2) 0.0380(9) Uani 1 1 d . . .
H20A H -0.1985 0.1226 0.5351 0.057 Uiso 1 1 calc R . .
H20B H -0.1160 0.1428 0.6136 0.057 Uiso 1 1 calc R . .
H20C H -0.0910 -0.0106 0.5700 0.057 Uiso 1 1 calc R . .
C21 C -0.0147(3) 0.2072(4) 0.15711(16) 0.0250(7) Uani 1 1 d . . .
C22 C 0.0486(4) 0.1490(4) 0.22105(19) 0.0370(9) Uani 1 1 d . . .
H22A H 0.0956 0.0502 0.2242 0.044 Uiso 1 1 calc R . .
C23 C 0.0444(4) 0.2334(4) 0.28119(17) 0.0356(8) Uani 1 1 d . . .
H23A H 0.0887 0.1919 0.3250 0.043 Uiso 1 1 calc R . .
C24 C -0.0235(3) 0.3766(4) 0.27770(17) 0.0263(7) Uani 1 1 d . . .
C25 C -0.0875(4) 0.4353(4) 0.21311(18) 0.0298(7) Uani 1 1 d . . .
H25A H -0.1346 0.5342 0.2100 0.036 Uiso 1 1 calc R . .
C26 C -0.0834(3) 0.3519(4) 0.15362(17) 0.0277(7) Uani 1 1 d . . .
H26A H -0.1277 0.3934 0.1098 0.033 Uiso 1 1 calc R . .
C27 C -0.0116(4) 0.1247(4) 0.09029(18) 0.0303(7) Uani 1 1 d . . .
N27 N 0.0593(4) -0.0083(4) 0.09303(19) 0.0414(9) Uani 1 1 d . . .
H27A H 0.061(5) -0.057(5) 0.058(3) 0.050 Uiso 1 1 d . . .
H27B H 0.089(5) -0.044(5) 0.131(3) 0.050 Uiso 1 1 d . . .
O27 O -0.0722(3) 0.1813(3) 0.03439(12) 0.0420(7) Uani 1 1 d . . .
C28 C -0.0303(5) 0.4725(4) 0.34142(18) 0.0356(9) Uani 1 1 d . . .
H28A H -0.0283 0.5867 0.3298 0.043 Uiso 1 1 calc R . .
H28B H -0.1192 0.4507 0.3549 0.043 Uiso 1 1 calc R . .
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'
B B 0.0013 0.0007 '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'
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
_geom_angle_publ_flag
N12 Ag1 N12 180.0 3_666 . ?
F1 B1 F3 109.9(7) . . ?
F1 B1 F2 112.5(7) . . ?
F3 B1 F2 110.0(7) . . ?
F1 B1 F4 108.0(7) . . ?
F3 B1 F4 110.5(7) . . ?
F2 B1 F4 106.0(7) . . ?
F5 B2 F6 111.3(9) . . ?
F5 B2 F8 109.9(8) . . ?
F6 B2 F8 108.2(8) . . ?
F5 B2 F7 107.4(8) . . ?
F6 B2 F7 110.8(8) . . ?
F8 B2 F7 109.2(8) . . ?
C11 N10 C18 107.1(3) . . ?
C11 N10 C28 125.0(3) . . ?
C18 N10 C28 127.9(3) . . ?
N12 C11 N10 112.6(3) . . ?
N12 C11 H11A 123.7 . . ?
N10 C11 H11A 123.7 . . ?
C11 N12 C13 105.5(3) . . ?
C11 N12 Ag1 126.4(3) . . ?
C13 N12 Ag1 127.7(2) . . ?
C14 C13 C18 120.8(3) . . ?
C14 C13 N12 130.0(3) . . ?
C18 C13 N12 109.2(3) . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
C14 C15 C16 120.7(3) . . ?
C14 C15 C19 119.4(3) . . ?
C16 C15 C19 119.9(3) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 C20 118.6(3) . . ?
C15 C16 C20 120.8(3) . . ?
C18 C17 C16 117.7(3) . . ?
C18 C17 H17A 121.2 . . ?
C16 C17 H17A 121.2 . . ?
N10 C18 C13 105.5(3) . . ?
N10 C18 C17 132.9(3) . . ?
C13 C18 C17 121.6(3) . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.8(3) . . ?
C22 C21 C27 123.5(3) . . ?
C26 C21 C27 117.7(3) . . ?
C21 C22 C23 120.6(3) . . ?
C21 C22 H22A 119.7 . . ?
C23 C22 H22A 119.7 . . ?
C24 C23 C22 120.5(3) . . ?
C24 C23 H23A 119.8 . . ?
C22 C23 H23A 119.8 . . ?
C23 C24 C25 118.9(3) . . ?
C23 C24 C28 122.4(3) . . ?
C25 C24 C28 118.8(3) . . ?
C26 C25 C24 120.6(3) . . ?
C26 C25 H25A 119.7 . . ?
C24 C25 H25A 119.7 . . ?
C25 C26 C21 120.5(3) . . ?
C25 C26 H26A 119.7 . . ?
C21 C26 H26A 119.7 . . ?
O27 C27 N27 121.4(3) . . ?
O27 C27 C21 120.7(3) . . ?
N27 C27 C21 117.9(3) . . ?
C27 N27 H27A 120(3) . . ?
C27 N27 H27B 117(3) . . ?
H27A N27 H27B 122(5) . . ?
N10 C28 C24 113.8(3) . . ?
N10 C28 H28A 108.8 . . ?
C24 C28 H28A 108.8 . . ?
N10 C28 H28B 108.8 . . ?
C24 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
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 N12 2.089(3) 3_666 ?
Ag1 N12 2.089(3) . ?
B1 F1 1.381(8) . ?
B1 F3 1.385(8) . ?
B1 F2 1.396(8) . ?
B1 F4 1.423(8) . ?
B2 F5 1.380(9) . ?
B2 F6 1.398(9) . ?
B2 F8 1.402(9) . ?
B2 F7 1.403(9) . ?
N10 C11 1.345(5) . ?
N10 C18 1.382(4) . ?
N10 C28 1.448(5) . ?
C11 N12 1.314(5) . ?
C11 H11A 0.9500 . ?
N12 C13 1.387(4) . ?
C13 C14 1.386(4) . ?
C13 C18 1.386(4) . ?
C14 C15 1.372(5) . ?
C14 H14A 0.9500 . ?
C15 C16 1.416(5) . ?
C15 C19 1.512(5) . ?
C16 C17 1.389(5) . ?
C16 C20 1.497(5) . ?
C17 C18 1.387(5) . ?
C17 H17A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.375(5) . ?
C21 C26 1.390(4) . ?
C21 C27 1.495(4) . ?
C22 C23 1.390(5) . ?
C22 H22A 0.9500 . ?
C23 C24 1.376(5) . ?
C23 H23A 0.9500 . ?
C24 C25 1.389(4) . ?
C24 C28 1.506(5) . ?
C25 C26 1.375(5) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 O27 1.234(4) . ?
C27 N27 1.317(5) . ?
N27 H27A 0.80(5) . ?
N27 H27B 0.80(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
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
N27 H27A O27 0.80(5) 2.13(5) 2.929(4) 178(5) 3
N27 H27B F2 0.80(5) 2.20(5) 2.902(11) 148(5) 2_545
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
C18 N10 C11 N12 0.7(4) . . . . ?
C28 N10 C11 N12 -177.4(3) . . . . ?
N10 C11 N12 C13 -0.4(4) . . . . ?
N10 C11 N12 Ag1 -173.9(2) . . . . ?
C11 N12 C13 C14 178.9(3) . . . . ?
Ag1 N12 C13 C14 -7.7(5) . . . . ?
C11 N12 C13 C18 -0.1(4) . . . . ?
Ag1 N12 C13 C18 173.4(2) . . . . ?
C18 C13 C14 C15 -0.8(5) . . . . ?
N12 C13 C14 C15 -179.7(3) . . . . ?
C13 C14 C15 C16 -1.0(5) . . . . ?
C13 C14 C15 C19 178.4(3) . . . . ?
C14 C15 C16 C17 1.4(5) . . . . ?
C19 C15 C16 C17 -178.0(3) . . . . ?
C14 C15 C16 C20 -178.9(3) . . . . ?
C19 C15 C16 C20 1.7(5) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C20 C16 C17 C18 -179.8(3) . . . . ?
C11 N10 C18 C13 -0.7(3) . . . . ?
C28 N10 C18 C13 177.3(3) . . . . ?
C11 N10 C18 C17 178.4(3) . . . . ?
C28 N10 C18 C17 -3.6(5) . . . . ?
C14 C13 C18 N10 -178.6(3) . . . . ?
N12 C13 C18 N10 0.5(3) . . . . ?
C14 C13 C18 C17 2.2(5) . . . . ?
N12 C13 C18 C17 -178.8(3) . . . . ?
C16 C17 C18 N10 179.3(3) . . . . ?
C16 C17 C18 C13 -1.7(5) . . . . ?
C26 C21 C22 C23 -0.1(6) . . . . ?
C27 C21 C22 C23 178.5(3) . . . . ?
C21 C22 C23 C24 0.1(6) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C22 C23 C24 C28 -179.7(4) . . . . ?
C23 C24 C25 C26 0.1(5) . . . . ?
C28 C24 C25 C26 179.7(4) . . . . ?
C24 C25 C26 C21 -0.1(5) . . . . ?
C22 C21 C26 C25 0.1(5) . . . . ?
C27 C21 C26 C25 -178.6(3) . . . . ?
C22 C21 C27 O27 178.8(4) . . . . ?
C26 C21 C27 O27 -2.5(5) . . . . ?
C22 C21 C27 N27 -2.1(5) . . . . ?
C26 C21 C27 N27 176.6(3) . . . . ?
C11 N10 C28 C24 74.7(4) . . . . ?
C18 N10 C28 C24 -103.0(4) . . . . ?
C23 C24 C28 N10 23.9(5) . . . . ?
C25 C24 C28 N10 -155.7(3) . . . . ?
