#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:39:03 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179540 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/09/4500928.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_4500928
loop_
_publ_author_name
'Hao, Hong-Jun'
'Sun, Di'
'Li, Yun-Hua'
'Liu, Fu-Jing'
'Huang, Rong-Bin'
'Zheng, Lan-Sun'
_publ_section_title
;
 Effect of Different Carboxylates on a Series of Ag(I) Coordination
 Compounds with Benzoguanamine Ligand
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3564
_journal_paper_doi               10.1021/cg200534x
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C14 H15 Ag N5 O3'
_chemical_formula_weight         409.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 96.5610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   20.9002(9)
_cell_length_b                   7.5329(3)
_cell_length_c                   19.6558(7)
_cell_measurement_reflns_used    7975
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      55.02
_cell_measurement_theta_min      6.04
_cell_volume                     3074.3(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9206
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    1.334
_exptl_absorpt_correction_T_max  0.8782
_exptl_absorpt_correction_T_min  0.8250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.730
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0293
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0536P)²+13.7777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                2672
_reflns_number_total             3006
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200534x_si_002.cif
_cod_data_source_block           p5
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4500928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
Ag1 Ag 0.364543(10) 0.37307(3) 0.242446(11) 0.02518(10) Uani 1 1 d .
C1 C 0.21967(14) 0.6819(4) 0.39185(14) 0.0219(6) Uani 1 1 d .
C2 C 0.31996(15) 0.5752(4) 0.38253(15) 0.0249(6) Uani 1 1 d .
C3 C 0.25063(15) 0.6207(4) 0.28677(15) 0.0209(6) Uani 1 1 d .
C4 C 0.23455(16) 0.6124(4) 0.21063(15) 0.0246(6) Uani 1 1 d .
C5 C 0.28095(18) 0.6633(4) 0.16840(17) 0.0330(7) Uani 1 1 d .
H5C H 0.3222 0.7036 0.1876 0.040 Uiso 1 1 calc R
C6 C 0.2655(2) 0.6536(5) 0.09745(18) 0.0472(11) Uani 1 1 d .
H6A H 0.2962 0.6896 0.0681 0.057 Uiso 1 1 calc R
C7 C 0.2062(3) 0.5924(5) 0.06991(18) 0.0518(12) Uani 1 1 d .
H7A H 0.1966 0.5850 0.0216 0.062 Uiso 1 1 calc R
C8 C 0.1604(2) 0.5414(5) 0.11163(17) 0.0434(9) Uani 1 1 d .
H8A H 0.1195 0.4995 0.0921 0.052 Uiso 1 1 calc R
C9 C 0.17494(17) 0.5521(4) 0.18281(15) 0.0305(7) Uani 1 1 d .
H9A H 0.1438 0.5178 0.2119 0.037 Uiso 1 1 calc R
C10 C 0.50964(15) 0.3355(4) 0.32368(16) 0.0270(6) Uani 1 1 d .
C11 C 0.50828(16) 0.1618(4) 0.28524(17) 0.0273(7) Uani 1 1 d .
C12 C 0.5194(2) 0.0034(5) 0.3201(2) 0.0481(10) Uani 1 1 d .
H12A H 0.5335 0.0034 0.3678 0.058 Uiso 1 1 calc R
C13 C 0.5097(3) -0.1562(5) 0.2847(3) 0.0662(14) Uani 1 1 d .
H13A H 0.5165 -0.2656 0.3085 0.079 Uiso 1 1 calc R
C14 C 0.5276(3) 0.7365(7) 0.4793(2) 0.0636(12) Uani 1 1 d .
H20C H 0.5098 0.6690 0.5154 0.076 Uiso 1 1 calc R
H20A H 0.4943 0.7531 0.4406 0.076 Uiso 1 1 calc R
H20B H 0.5425 0.8526 0.4973 0.076 Uiso 1 1 calc R
N1 N 0.30841(12) 0.5654(3) 0.31256(12) 0.0221(5) Uani 1 1 d .
N2 N 0.20420(12) 0.6825(3) 0.32195(12) 0.0206(5) Uani 1 1 d .
N3 N 0.27655(13) 0.6310(3) 0.42328(13) 0.0252(6) Uani 1 1 d .
N4 N 0.17494(12) 0.7368(4) 0.42946(12) 0.0274(6) Uani 1 1 d .
H4A H 0.1830 0.7392 0.4744 0.033 Uiso 1 1 calc R
H4B H 0.1371 0.7710 0.4096 0.033 Uiso 1 1 calc R
N5 N 0.37748(14) 0.5272(4) 0.41100(14) 0.0375(7) Uani 1 1 d .
H5A H 0.3868 0.5320 0.4558 0.045 Uiso 1 1 calc R
H5B H 0.4066 0.4903 0.3852 0.045 Uiso 1 1 calc R
O1 O 0.46016(10) 0.4302(3) 0.31349(11) 0.0275(5) Uani 1 1 d .
O2 O 0.55859(13) 0.3779(4) 0.36319(16) 0.0496(7) Uani 1 1 d .
O3 O 0.58005(16) 0.6425(4) 0.45729(15) 0.0559(8) Uani 1 1 d .
H3C H 0.5664 0.5675 0.4291 0.067 Uiso 1 1 d 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'
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
_geom_angle_publ_flag
N2 Ag1 O1 151.33(8) 4_545 . y
N2 Ag1 N1 112.15(9) 4_545 . y
O1 Ag1 N1 89.22(8) . . y
N4 C1 N3 118.8(3) . . ?
N4 C1 N2 117.2(3) . . ?
N3 C1 N2 124.1(3) . . ?
N5 C2 N3 118.6(3) . . ?
N5 C2 N1 117.3(3) . . ?
N3 C2 N1 124.1(3) . . ?
N1 C3 N2 126.6(3) . . ?
N1 C3 C4 117.4(3) . . ?
N2 C3 C4 116.0(3) . . ?
C9 C4 C5 120.7(3) . . ?
C9 C4 C3 120.0(3) . . ?
C5 C4 C3 119.3(3) . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 H5C 120.6 . . ?
C4 C5 H5C 120.6 . . ?
C7 C6 C5 120.4(4) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7A 119.6 . . ?
C8 C7 H7A 119.6 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 H8A 120.3 . . ?
C9 C8 H8A 120.3 . . ?
C4 C9 C8 119.9(3) . . ?
C4 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
O2 C10 O1 123.7(3) . . ?
O2 C10 C11 119.9(3) . . ?
O1 C10 C11 116.4(3) . . ?
C12 C11 C11 120.2(2) . 2_655 ?
C12 C11 C10 120.5(3) . . ?
C11 C11 C10 119.16(18) 2_655 . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C13 C13 C12 120.3(3) 2_655 . ?
C13 C13 H13A 119.9 2_655 . ?
C12 C13 H13A 119.9 . . ?
O3 C14 H20C 109.5 . . ?
O3 C14 H20A 109.5 . . ?
H20C C14 H20A 109.5 . . ?
O3 C14 H20B 109.5 . . ?
H20C C14 H20B 109.5 . . ?
H20A C14 H20B 109.5 . . ?
C3 N1 C2 114.6(2) . . ?
C3 N1 Ag1 117.10(19) . . ?
C2 N1 Ag1 124.59(19) . . ?
C3 N2 C1 114.4(3) . . ?
C3 N2 Ag1 112.11(18) . 4 ?
C1 N2 Ag1 127.70(19) . 4 ?
C1 N3 C2 116.2(3) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C2 N5 H5A 120.0 . . ?
C2 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C10 O1 Ag1 128.5(2) . . ?
C14 O3 H3C 109.3 . . ?
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 N2 2.304(2) 4_545 y
Ag1 O1 2.343(2) . y
Ag1 N1 2.397(2) . y
C1 N4 1.323(4) . ?
C1 N3 1.332(4) . ?
C1 N2 1.375(4) . ?
C2 N5 1.318(4) . ?
C2 N3 1.344(4) . ?
C2 N1 1.371(4) . ?
C3 N1 1.322(4) . ?
C3 N2 1.338(4) . ?
C3 C4 1.497(4) . ?
C4 C9 1.379(5) . ?
C4 C5 1.400(5) . ?
C5 C6 1.397(5) . ?
C5 H5C 0.9500 . ?
C6 C7 1.374(7) . ?
C6 H6A 0.9500 . ?
C7 C8 1.384(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.400(4) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 O2 1.253(4) . ?
C10 O1 1.253(4) . ?
C10 C11 1.510(4) . ?
C11 C12 1.382(5) . ?
C11 C11 1.389(7) 2_655 ?
C12 C13 1.392(6) . ?
C12 H12A 0.9500 . ?
C13 C13 1.378(10) 2_655 ?
C13 H13A 0.9500 . ?
C14 O3 1.413(6) . ?
C14 H20C 0.9800 . ?
C14 H20A 0.9800 . ?
C14 H20B 0.9800 . ?
N2 Ag1 2.304(2) 4 ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
O3 H3C 0.8199 . ?
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
O3 H3C O2 0.82 1.92 2.721(4) 164.6 .
N5 H5B O1 0.88 1.95 2.820(3) 168.7 .
N5 H5A O3 0.88 2.20 2.932(4) 139.9 5_666
N4 H4B O2 0.88 1.96 2.831(4) 172.2 3_455
N4 H4A N3 0.88 2.31 3.119(4) 153.2 7_566
