#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/34/4513468.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_4513468
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            'C16 H17 N5 O2 S2'
_chemical_formula_weight         375.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 113.288(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9493(9)
_cell_length_b                   8.3273(4)
_cell_length_c                   16.9440(9)
_cell_measurement_reflns_used    3699
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.93
_cell_volume                     1807.9(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7722
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.8099
_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    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0084(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0432
_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)+(0.0628P)²+0.4018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                2695
_reflns_number_total             3699
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b00529_si_002.cif
_cod_data_source_block           bzamH.stz
_cod_depositor_comments
'Adding full bibliography for 4513461--4513471.cif.'
_cod_original_cell_volume        1807.87(17)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4513468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
S1 S 0.20706(5) 0.64402(7) 1.01858(3) 0.04582(19) Uani 1 1 d
S2 S 0.42532(6) 0.79814(10) 1.15589(4) 0.0703(3) Uani 1 1 d
N3 N 0.23068(14) 0.6589(2) 1.11683(11) 0.0470(5) Uani 1 1 d
O2 O 0.09578(13) 0.6224(2) 0.97515(11) 0.0652(5) Uani 1 1 d
O1 O 0.25029(15) 0.77329(19) 0.98579(10) 0.0613(5) Uani 1 1 d
N4 N 0.34716(17) 0.6883(3) 1.25833(12) 0.0605(6) Uani 1 1 d
N5 N 0.3820(2) 0.0349(4) 0.95370(18) 0.0688(7) Uani 1 1 d
N1 N 0.16330(19) 0.8560(3) 0.79778(15) 0.0623(6) Uani 1 1 d
N2 N 0.05824(19) 0.9347(3) 0.66303(12) 0.0570(6) Uani 1 1 d
H1B H 0.169(3) 0.822(4) 0.844(2) 0.085(10) Uiso 1 1 d
H2 H -0.121(2) 0.820(3) 0.674(2) 0.080(9) Uiso 1 1 d
H3 H -0.249(3) 0.845(4) 0.725(2) 0.093(12) Uiso 1 1 d
H6 H 0.068(2) 1.033(3) 0.8770(18) 0.061(8) Uiso 1 1 d
H5 H -0.060(2) 1.066(4) 0.927(2) 0.092(10) Uiso 1 1 d
H1A H 0.214(2) 0.844(3) 0.7845(19) 0.065(8) Uiso 1 1 d
H2B H 0.003(2) 0.988(3) 0.6299(16) 0.053(7) Uiso 1 1 d
H4 H -0.230(3) 0.979(4) 0.845(2) 0.100(11) Uiso 1 1 d
H2A H 0.114(2) 0.913(3) 0.6490(16) 0.058(7) Uiso 1 1 d
H5B H 0.354(3) -0.050(4) 0.962(2) 0.084(12) Uiso 1 1 d
H16 H 0.1792(19) 0.316(3) 1.0453(16) 0.057(7) Uiso 1 1 d
H13 H 0.432(2) 0.325(3) 0.9311(18) 0.071(8) Uiso 1 1 d
H15 H 0.2401(17) 0.082(3) 1.0158(14) 0.050(6) Uiso 1 1 d
H10 H 0.556(3) 0.860(4) 1.280(2) 0.093(11) Uiso 1 1 d
H12 H 0.3624(18) 0.566(3) 0.9571(15) 0.050(6) Uiso 1 1 d
H5A H 0.423(3) 0.044(5) 0.931(3) 0.126(16) Uiso 1 1 d
C8 C 0.32515(17) 0.7051(3) 1.17595(13) 0.0441(5) Uani 1 1 d
C9 C 0.4443(2) 0.7497(4) 1.30703(18) 0.0734(8) Uani 1 1 d
C10 C 0.4977(3) 0.8094(5) 1.2651(2) 0.0803(10) Uani 1 1 d
C11 C 0.26545(17) 0.4664(2) 1.00351(12) 0.0411(5) Uani 1 1 d
C12 C 0.34260(19) 0.4674(3) 0.97177(15) 0.0517(6) Uani 1 1 d
C13 C 0.3825(2) 0.3254(3) 0.95648(17) 0.0568(6) Uani 1 1 d
C14 C 0.34518(17) 0.1782(3) 0.97152(14) 0.0481(6) Uani 1 1 d
C15 C 0.26984(19) 0.1790(3) 1.00623(15) 0.0485(6) Uani 1 1 d
C16 C 0.23084(19) 0.3207(3) 1.02187(14) 0.0476(6) Uani 1 1 d
C1 C -0.01286(18) 0.9272(3) 0.77212(13) 0.0474(5) Uani 1 1 d
C2 C -0.1118(2) 0.8747(4) 0.72273(17) 0.0675(8) Uani 1 1 d
C3 C -0.1905(3) 0.8917(5) 0.7519(2) 0.0827(10) Uani 1 1 d
C4 C -0.1723(3) 0.9624(4) 0.8285(2) 0.0808(10) Uani 1 1 d
C5 C -0.0749(3) 1.0160(4) 0.8778(2) 0.0806(10) Uani 1 1 d
C6 C 0.0056(3) 0.9977(4) 0.85090(17) 0.0644(8) Uani 1 1 d
C7 C 0.07306(18) 0.9056(3) 0.74292(13) 0.0480(5) Uani 1 1 d
H9 H 0.468(2) 0.746(4) 1.368(2) 0.082(9) 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'
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'
N N 0.0061 0.0033 '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
O2 S1 O1 115.12(11)
O2 S1 N3 106.46(11)
O1 S1 N3 113.82(10)
O2 S1 C11 106.76(10)
O1 S1 C11 106.44(10)
N3 S1 C11 107.83(10)
C10 S2 C8 89.40(14)
C8 N3 S1 122.71(15)
C8 N4 C9 111.0(2)
C14 N5 H5B 116(2)
C14 N5 H5A 114(3)
H5B N5 H5A 129(4)
C7 N1 H1B 120(2)
C7 N1 H1A 122(2)
H1B N1 H1A 117(3)
C7 N2 H2B 119.6(16)
C7 N2 H2A 115.4(16)
H2B N2 H2A 124(2)
N4 C8 N3 120.3(2)
N4 C8 S2 112.69(17)
N3 C8 S2 126.91(16)
C10 C9 N4 116.8(3)
C10 C9 H9 125.1(18)
N4 C9 H9 118.1(18)
C9 C10 S2 110.1(2)
C9 C10 H10 135(2)
S2 C10 H10 115(2)
C12 C11 C16 119.2(2)
C12 C11 S1 121.98(17)
C16 C11 S1 118.83(17)
C13 C12 C11 120.3(2)
C13 C12 H12 121.6(14)
C11 C12 H12 118.0(14)
C12 C13 C14 120.9(2)
C12 C13 H13 120.5(16)
C14 C13 H13 118.4(16)
N5 C14 C15 120.3(2)
N5 C14 C13 121.5(2)
C15 C14 C13 118.2(2)
C16 C15 C14 120.7(2)
C16 C15 H15 117.7(14)
C14 C15 H15 121.4(14)
C15 C16 C11 120.7(2)
C15 C16 H16 118.0(15)
C11 C16 H16 121.2(15)
C2 C1 C6 118.8(2)
C2 C1 C7 120.7(2)
C6 C1 C7 120.5(2)
C1 C2 C3 120.0(3)
C1 C2 H2 118(2)
C3 C2 H2 122(2)
C4 C3 C2 120.9(3)
C4 C3 H3 119(2)
C2 C3 H3 119(2)
C3 C4 C5 119.7(3)
C3 C4 H4 119(2)
C5 C4 H4 121(2)
C4 C5 C6 120.5(3)
C4 C5 H5 123(2)
C6 C5 H5 116(2)
C5 C6 C1 120.0(3)
C5 C6 H6 125.6(19)
C1 C6 H6 114.2(19)
N1 C7 N2 120.7(2)
N1 C7 C1 118.9(2)
N2 C7 C1 120.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4424(18)
S1 O1 1.4478(17)
S1 N3 1.5690(18)
S1 C11 1.755(2)
S2 C10 1.725(3)
S2 C8 1.745(2)
N3 C8 1.358(3)
N4 C8 1.313(3)
N4 C9 1.376(3)
N5 C14 1.379(3)
N5 H5B 0.84(3)
N5 H5A 0.81(4)
N1 C7 1.302(3)
N1 H1B 0.81(3)
N1 H1A 0.83(3)
N2 C7 1.309(3)
N2 H2B 0.87(3)
N2 H2A 0.91(3)
C9 C10 1.314(4)
C9 H9 0.95(3)
C10 H10 0.87(3)
C11 C12 1.380(3)
C11 C16 1.386(3)
C12 C13 1.375(4)
C12 H12 0.93(2)
C13 C14 1.394(3)
C13 H13 0.95(3)
C14 C15 1.392(3)
C15 C16 1.368(3)
C15 H15 0.95(2)
C16 H16 0.95(3)
C1 C2 1.372(4)
C1 C6 1.386(3)
C1 C7 1.477(3)
C2 C3 1.378(4)
C2 H2 0.90(3)
C3 C4 1.355(5)
C3 H3 0.85(3)
C4 C5 1.358(5)
C4 H4 0.96(4)
C5 C6 1.378(4)
C5 H5 0.87(3)
C6 H6 0.85(3)
