#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/34/4513471.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_4513471
loop_
_publ_author_name
'Kamali, Naghmeh'
'Aljohani, Marwah'
'McArdle, Patrick'
'Erxleben, Andrea'
_publ_section_title
;
 Hydrogen Bonding Networks and Solid-State Conversions in Benzamidinium
 Salts
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3905
_journal_paper_doi               10.1021/acs.cgd.5b00529
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C10 H12 N5 O3.5'
_chemical_formula_weight         258.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.035(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1599(15)
_cell_length_b                   7.1495(11)
_cell_length_c                   13.5183(14)
_cell_measurement_reflns_used    2156
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      3.01
_cell_volume                     1175.2(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1048
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7240
_diffrn_reflns_theta_full        25.33
_diffrn_reflns_theta_max         25.33
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
(compiled Jan  8 2009,16:24:04)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0449
_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)+(0.0621P)²+0.2685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                1654
_reflns_number_total             2156
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00529_si_002.cif
_cod_data_source_block           bzamH.cya
_cod_depositor_comments
'Adding full bibliography for 4513461--4513471.cif.'
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4513471
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O 1.01361(11) 0.4441(2) -0.12994(10) 0.0406(4) Uani 1 1 d .
O1 O 0.72155(12) 0.3451(2) 0.06794(10) 0.0422(4) Uani 1 1 d .
O2 O 0.68572(12) 0.2883(2) -0.26470(10) 0.0405(4) Uani 1 1 d .
N5 N 0.84943(13) 0.3615(2) -0.19797(12) 0.0303(4) Uani 1 1 d .
H5A H 0.8774 0.3614 -0.2564 0.042(6) Uiso 1 1 calc R
N3 N 0.69305(13) 0.3142(2) -0.09781(12) 0.0299(4) Uani 1 1 d .
N4 N 0.86597(13) 0.3925(2) -0.03105(12) 0.0310(4) Uani 1 1 d .
H4A H 0.9050 0.4147 0.0207 0.043(6) Uiso 1 1 calc R
O1W O 0.5000 -0.0730(3) 0.2500 0.0309(5) Uani 1 2 d S
N2 N 0.45230(14) 0.3129(2) -0.05156(12) 0.0324(4) Uani 1 1 d .
H2A H 0.5187 0.3359 -0.0698 0.038(6) Uiso 1 1 calc R
H2B H 0.3982 0.3421 -0.0896 0.047(7) Uiso 1 1 calc R
N1 N 0.51507(14) 0.1882(2) 0.09257(13) 0.0374(5) Uani 1 1 d .
H1A H 0.5817 0.2108 0.0749 0.046(7) Uiso 1 1 calc R
H1B H 0.5021 0.1360 0.1487 0.054(8) Uiso 1 1 calc R
C1 C 0.31972(16) 0.1925(3) 0.06594(15) 0.0288(5) Uani 1 1 d .
C2 C 0.24000(18) 0.1462(3) -0.00254(17) 0.0376(5) Uani 1 1 d .
H2 H 0.2576 0.1394 -0.0694 0.030(5) Uiso 1 1 calc R
C3 C 0.13453(19) 0.1102(3) 0.0284(2) 0.0510(7) Uani 1 1 d .
H3 H 0.0807 0.0790 -0.0177 0.054(7) Uiso 1 1 calc R
C4 C 0.1081(2) 0.1201(3) 0.1276(2) 0.0525(7) Uani 1 1 d .
H4 H 0.0367 0.0945 0.1481 0.057(7) Uiso 1 1 calc R
C5 C 0.1865(2) 0.1673(3) 0.19572(19) 0.0472(6) Uani 1 1 d .
H5 H 0.1683 0.1748 0.2624 0.062(8) Uiso 1 1 calc R
C6 C 0.29222(18) 0.2036(3) 0.16531(16) 0.0360(5) Uani 1 1 d .
H6 H 0.3456 0.2358 0.2116 0.048(7) Uiso 1 1 calc R
C7 C 0.43354(16) 0.2333(3) 0.03416(14) 0.0270(5) Uani 1 1 d .
C8 C 0.75604(16) 0.3491(3) -0.01796(14) 0.0287(5) Uani 1 1 d .
C9 C 0.91593(15) 0.4023(3) -0.12048(14) 0.0277(5) Uani 1 1 d .
C10 C 0.73828(16) 0.3198(3) -0.18802(14) 0.0274(5) Uani 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 N5 C10 123.44(17)
C9 N5 H5A 118.3
C10 N5 H5A 118.3
C10 N3 C8 119.40(16)
C9 N4 C8 124.00(16)
C9 N4 H4A 118.0
C8 N4 H4A 118.0
C7 N2 H2A 120.0
C7 N2 H2B 120.0
H2A N2 H2B 120.0
C7 N1 H1A 120.0
C7 N1 H1B 120.0
H1A N1 H1B 120.0
C2 C1 C6 119.58(19)
C2 C1 C7 120.64(18)
C6 C1 C7 119.77(18)
C3 C2 C1 119.8(2)
C3 C2 H2 120.1
C1 C2 H2 120.1
C2 C3 C4 120.3(2)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 120.3(2)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 119.8(2)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C1 120.3(2)
C5 C6 H6 119.8
C1 C6 H6 119.8
N1 C7 N2 120.56(18)
N1 C7 C1 119.06(17)
N2 C7 C1 120.38(17)
O1 C8 N3 123.78(18)
O1 C8 N4 116.99(17)
N3 C8 N4 119.23(17)
O3 C9 N5 123.18(17)
O3 C9 N4 122.56(17)
N5 C9 N4 114.26(16)
O2 C10 N3 123.03(17)
O2 C10 N5 117.34(17)
N3 C10 N5 119.63(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C9 1.231(2)
O1 C8 1.235(2)
O2 C10 1.238(2)
N5 C9 1.355(2)
N5 C10 1.391(2)
N5 H5A 0.8600
N3 C10 1.339(2)
N3 C8 1.346(3)
N4 C9 1.355(2)
N4 C8 1.384(2)
N4 H4A 0.8600
N2 C7 1.311(2)
N2 H2A 0.8600
N2 H2B 0.8600
N1 C7 1.307(3)
N1 H1A 0.8600
N1 H1B 0.8600
C1 C2 1.380(3)
C1 C6 1.387(3)
C1 C7 1.478(3)
C2 C3 1.374(3)
C2 H2 0.9300
C3 C4 1.381(4)
C3 H3 0.9300
C4 C5 1.368(4)
C4 H4 0.9300
C5 C6 1.375(3)
C5 H5 0.9300
C6 H6 0.9300
