#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/36/2213682.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213682
loop_
_publ_author_name
'Pereira Silva, P. S.'
'Ramos Silva, M.'
'Paixão, J. A.'
'Matos Beja, A.'
_publ_section_title
;
 Guanidinium benzoate
;
_journal_coeditor_code           BT2327
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2783
_journal_page_last               o2783
_journal_paper_doi               10.1107/S1600536807015802
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C H6 N3 + , C7 H5 O2 -'
_chemical_formula_moiety         'C H6 N3 + , C7 H5 O2 -'
_chemical_formula_sum            'C8 H11 N3 O2'
_chemical_formula_weight         181.20
_chemical_name_systematic
;
Guanidinium benzoate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7347(8)
_cell_length_b                   8.1216(4)
_cell_length_c                   7.8885(4)
_cell_measurement_reflns_used    6505
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6181
_cell_measurement_theta_min      2.8885
_cell_volume                     1008.08(9)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX2 CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0114
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27265
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         2.59
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.087
_refine_diff_density_min         -0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0354
_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)+(0.0512P)²+0.1512P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                735
_reflns_number_total             960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2327.cif
_cod_data_source_block           I
_cod_database_code               2213682
_cod_database_fobs_code          2213682
loop_
_symmetry_equiv_pos_as_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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.14899(6) 0.11435(12) 0.01484(12) 0.0621(4) Uani d . 1
C C1 0.21113(11) 0.7500 0.1719(2) 0.0487(5) Uani d S 1
C C2 0.11899(11) 0.2500 0.0607(2) 0.0466(5) Uani d S 1
C C3 0.04384(11) 0.2500 0.1780(2) 0.0509(5) Uani d S 1
C C4 0.00836(10) 0.1032(2) 0.2325(2) 0.0684(5) Uani d . 1
H H4 0.0313 0.0038 0.1962 0.082 Uiso calc R 1
C C5 -0.06091(10) 0.1034(3) 0.3405(2) 0.0913(6) Uani d . 1
H H5 -0.0842 0.0044 0.3773 0.110 Uiso calc R 1
C C6 -0.09507(17) 0.2500 0.3930(3) 0.0990(10) Uani d S 1
H H6 -0.1419 0.2500 0.4650 0.119 Uiso calc SR 1
N N1 0.23780(9) 0.60957(15) 0.23598(18) 0.0634(4) Uani d . 1
H H1A 0.2775(10) 0.6096(19) 0.323(2) 0.076 Uiso d . 1
H H1B 0.2182(9) 0.521(2) 0.191(2) 0.076 Uiso d . 1
N N2 0.15725(12) 0.7500 0.0424(2) 0.0648(5) Uani d S 1
H H2 0.1368(10) 0.848(2) 0.0030(19) 0.078 Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0749(7) 0.0404(6) 0.0709(7) 0.0054(4) 0.0148(5) 0.0038(5)
C1 0.0506(10) 0.0433(10) 0.0520(11) 0.000 -0.0003(9) 0.000
C2 0.0538(10) 0.0399(11) 0.0462(10) 0.000 -0.0039(8) 0.000
C3 0.0517(11) 0.0592(12) 0.0418(10) 0.000 -0.0069(8) 0.000
C4 0.0633(9) 0.0781(11) 0.0638(9) -0.0054(7) 0.0006(7) 0.0148(8)
C5 0.0696(11) 0.1285(17) 0.0757(12) -0.0177(11) 0.0059(9) 0.0298(12)
C6 0.0653(16) 0.170(3) 0.0618(16) 0.000 0.0113(12) 0.000
N1 0.0737(9) 0.0417(7) 0.0748(9) 0.0040(6) -0.0205(7) -0.0017(6)
N2 0.0758(12) 0.0506(11) 0.0680(11) 0.000 -0.0234(10) 0.000
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N1 8_575 . 120.12(18) ?
N1 C1 N2 8_575 . 119.94(9) ?
N1 C1 N2 . . 119.94(9) ?
O1 C2 O1 8_565 . 123.29(17) yes
O1 C2 C3 8_565 . 118.35(9) ?
O1 C2 C3 . . 118.35(9) ?
C4 C3 C4 . 8_565 118.83(19) ?
C4 C3 C2 . . 120.58(10) ?
C4 C3 C2 8_565 . 120.59(10) ?
C5 C4 C3 . . 120.54(17) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C6 C5 C4 . . 119.7(2) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C5 8_565 . 120.6(2) ?
C5 C6 H6 8_565 . 119.7 ?
C5 C6 H6 . . 119.7 ?
C1 N1 H1A . . 119.9(10) ?
C1 N1 H1B . . 117.1(11) ?
H1A N1 H1B . . 123.0(15) ?
C1 N2 H2 . . 119.1(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.2519(13) yes
C1 N1 8_575 1.3162(15) ?
C1 N1 . 1.3162(15) yes
C1 N2 . 1.328(3) yes
C2 O1 8_565 1.2519(13) ?
C2 C3 . 1.502(3) ?
C3 C4 . 1.3846(17) ?
C3 C4 8_565 1.3846(17) ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.371(2) ?
C5 H5 . 0.9300 ?
C6 C5 8_565 1.371(2) ?
C6 H6 . 0.9300 ?
N1 H1A . 0.931(18) ?
N1 H1B . 0.860(17) ?
N2 H2 . 0.915(18) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 7_666 0.931(18) 1.902(19) 2.8309(17) 175.1(14)
N2 H2 O1 1_565 0.915(18) 2.171(19) 2.9700(10) 145.4(14)
N1 H1B O1 8_565 0.860(17) 2.081(17) 2.8816(17) 154.7(15)
