#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/95/2219553.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_2219553
loop_
_publ_author_name
'Karapetyan, Harutyun A.'
_publ_section_title
;
 <small>L</small>-Argininium ethyl sulfate
;
_journal_coeditor_code           CV2443
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1982
_journal_paper_doi               10.1107/S1600536808029954
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C6 H15 N4 O2 +, C2 H5 O4 S -'
_chemical_formula_moiety         'C6 H15 N4 O2 +, C2 H5 O4 S -'
_chemical_formula_sum            'C8 H20 N4 O6 S'
_chemical_formula_weight         300.34
_chemical_name_systematic
;
L-Argininium ethyl sulfate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1504(18)
_cell_length_b                   12.519(3)
_cell_length_c                   12.551(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      14
_cell_volume                     1437.8(6)
_computing_cell_refinement       'LS in CAD-4 Manual (Enraf--Nonius, 1988)'
_computing_data_collection
'DATCOL in CAD-4 Manual (Enraf--Nonius, 1988)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4566
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 400
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.736
_refine_diff_density_min         -0.592
_refine_ls_abs_structure_details 'Flack (1983), 1775 Friedel pairs'
_refine_ls_abs_structure_Flack   0.05(16)
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         4171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0715
_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)+(0.0927P)²+1.2922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1822
_refine_ls_wR_factor_ref         0.2023
_reflns_number_gt                3091
_reflns_number_total             4171
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2443.cif
_cod_data_source_block           I
_cod_original_cell_volume        1437.8(5)
_cod_original_formula_sum        'C8 H20 N4 O6 S1'
_cod_database_code               2219553
_cod_database_fobs_code          2219553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
S S1 0.23564(11) 0.86276(9) 0.82316(10) 0.0575(3) Uani d . 1
O O1 0.1060(2) 0.6386(2) 0.5342(2) 0.0447(6) Uani d . 1
O O2 0.3427(3) 0.6749(2) 0.5555(3) 0.0541(8) Uani d . 1
O O3 0.3324(5) 0.7594(3) 0.8318(5) 0.126(2) Uani d . 1
O O4 0.0977(4) 0.8395(4) 0.7810(5) 0.114(2) Uani d . 1
O O5 0.3241(6) 0.9208(6) 0.7447(3) 0.126(2) Uani d . 1
O O6 0.2501(5) 0.9140(2) 0.9236(3) 0.0755(11) Uani d . 1
N N1 0.3133(3) 0.8825(2) 0.5232(2) 0.0331(5) Uani d . 1
H H1A 0.3969 0.8533 0.5017 0.050 Uiso calc R 1
H H1B 0.3140 0.8890 0.5938 0.050 Uiso calc R 1
H H1C 0.3032 0.9467 0.4937 0.050 Uiso calc R 1
N N2 0.1657(4) 0.7002(3) 0.1525(2) 0.0450(7) Uani d . 1
H H2 0.0751 0.7186 0.1518 0.054 Uiso calc R 1
N N3 0.0934(4) 0.5395(3) 0.0841(3) 0.0531(9) Uani d . 1
H H3A 0.1139 0.4759 0.0629 0.064 Uiso calc R 1
H H3B 0.0051 0.5627 0.0803 0.064 Uiso calc R 1
N N4 0.3325(4) 0.5638(3) 0.1274(3) 0.0519(9) Uani d . 1
H H4A 0.4024 0.6035 0.1505 0.062 Uiso calc R 1
H H4B 0.3503 0.4994 0.1074 0.062 Uiso calc R 1
C C1 0.2151(3) 0.6992(3) 0.5313(3) 0.0340(6) Uani d . 1
C C2 0.1889(3) 0.8130(2) 0.4905(2) 0.0296(6) Uani d . 1
H H1 0.0993 0.8406 0.5233 0.036 Uiso calc R 1
C C3 0.1696(3) 0.8141(3) 0.3697(2) 0.0332(6) Uani d . 1
H H3C 0.0883 0.7678 0.3515 0.040 Uiso calc R 1
H H3D 0.1437 0.8860 0.3479 0.040 Uiso calc R 1
C C4 0.3030(4) 0.7788(3) 0.3057(3) 0.0392(7) Uani d . 1
H H4C 0.3842 0.8262 0.3209 0.047 Uiso calc R 1
H H4D 0.3309 0.7072 0.3272 0.047 Uiso calc R 1
C C5 0.2713(4) 0.7799(3) 0.1865(3) 0.0408(7) Uani d . 1
H H5A 0.2353 0.8501 0.1670 0.049 Uiso calc R 1
H H5B 0.3621 0.7683 0.1483 0.049 Uiso calc R 1
C C6 0.1980(4) 0.6018(3) 0.1226(3) 0.0400(8) Uani d . 1
C C7 0.2636(9) 0.6578(5) 0.8418(6) 0.100(2) Uani d . 1
H H7A 0.2037 0.6434 0.7797 0.120 Uiso calc R 1
H H7B 0.2012 0.6567 0.9043 0.120 Uiso calc R 1
C C8 0.3784(9) 0.5765(5) 0.8517(5) 0.098(2) Uani d . 1
H H8A 0.4249 0.5665 0.7838 0.147 Uiso calc R 1
H H8B 0.3359 0.5103 0.8747 0.147 Uiso calc R 1
H H8C 0.4496 0.5996 0.9029 0.147 Uiso calc R 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_publ_flag
O4 S1 O6 120.9(3) n
O4 S1 O5 110.3(3) n
O6 S1 O5 108.7(3) n
O4 S1 O3 111.3(3) n
O6 S1 O3 105.0(3) n
O5 S1 O3 98.2(4) n
C7 O3 S1 119.5(4) n
C2 N1 H1A 109.5 n
C2 N1 H1B 109.5 n
H1A N1 H1B 109.5 n
C2 N1 H1C 109.5 n
H1A N1 H1C 109.5 n
H1B N1 H1C 109.5 n
C6 N2 C5 125.1(3) n
C6 N2 H2 117.5 n
C5 N2 H2 117.5 n
C6 N3 H3A 120.0 n
C6 N3 H3B 120.0 n
H3A N3 H3B 120.0 n
C6 N4 H4A 120.0 n
C6 N4 H4B 120.0 n
H4A N4 H4B 120.0 n
O2 C1 O1 126.3(3) n
O2 C1 C2 117.1(3) n
O1 C1 C2 116.6(3) n
N1 C2 C3 110.9(2) n
N1 C2 C1 109.3(2) n
C3 C2 C1 111.0(3) n
N1 C2 H1 108.5 n
C3 C2 H1 108.5 n
C1 C2 H1 108.5 n
C4 C3 C2 115.3(3) n
C4 C3 H3C 108.4 n
C2 C3 H3C 108.4 n
C4 C3 H3D 108.4 n
C2 C3 H3D 108.4 n
H3C C3 H3D 107.5 n
C5 C4 C3 111.2(3) n
C5 C4 H4C 109.4 n
C3 C4 H4C 109.4 n
C5 C4 H4D 109.4 n
C3 C4 H4D 109.4 n
H4C C4 H4D 108.0 n
N2 C5 C4 114.1(3) n
N2 C5 H5A 108.7 n
C4 C5 H5A 108.7 n
N2 C5 H5B 108.7 n
C4 C5 H5B 108.7 n
H5A C5 H5B 107.6 n
N4 C6 N2 122.1(3) n
N4 C6 N3 118.5(3) n
N2 C6 N3 119.4(3) n
O3 C7 C8 108.1(6) n
O3 C7 H7A 110.1 n
C8 C7 H7A 110.1 n
O3 C7 H7B 110.1 n
C8 C7 H7B 110.1 n
H7A C7 H7B 108.4 n
C7 C8 H8A 109.5 n
C7 C8 H8B 109.5 n
H8A C8 H8B 109.5 n
C7 C8 H8C 109.5 n
H8A C8 H8C 109.5 n
H8B C8 H8C 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O4 1.399(4) n
S1 O6 1.421(3) n
S1 O5 1.468(5) n
S1 O3 1.571(4) n
O1 C1 1.255(4) n
O2 C1 1.244(4) n
O3 C7 1.426(7) n
N1 C2 1.490(4) n
N1 H1A 0.8900 n
N1 H1B 0.8900 n
N1 H1C 0.8900 n
N2 C6 1.322(5) n
N2 C5 1.453(5) n
N2 H2 0.8600 n
N3 C6 1.326(5) n
N3 H3A 0.8600 n
N3 H3B 0.8600 n
N4 C6 1.321(5) n
N4 H4A 0.8600 n
N4 H4B 0.8600 n
C1 C2 1.533(4) n
C2 C3 1.527(4) n
C2 H1 0.9800 n
C3 C4 1.526(4) n
C3 H3C 0.9700 n
C3 H3D 0.9700 n
C4 C5 1.524(5) n
C4 H4C 0.9700 n
C4 H4D 0.9700 n
C5 H5A 0.9700 n
C5 H5B 0.9700 n
C7 C8 1.467(9) n
C7 H7A 0.9700 n
C7 H7B 0.9700 n
C8 H8A 0.9600 n
C8 H8B 0.9600 n
C8 H8C 0.9600 n
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 H1B O5 1_555 0.89 1.94 2.823(5) 172.9
N1 H1C O6 2_574 0.89 2.01 2.896(4) 171.7
N1 H1A O1 4_566 0.89 1.97 2.786(4) 152.1
N2 H2 O3 4_466 0.86 2.25 3.098(6) 169.7
N3 H3B O6 4_466 0.86 2.35 3.196(5) 167.2
N3 H3A O2 2_564 0.86 1.93 2.771(4) 164.7
N4 H4B O1 2_564 0.86 2.00 2.847(4) 169.5
N4 H4A O4 4_566 0.86 2.11 2.945(5) 164.5
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_publ_flag
O4 S1 O3 C7 -25.9(8) n
O6 S1 O3 C7 106.5(6) n
O5 S1 O3 C7 -141.5(6) n
O2 C1 C2 N1 -19.4(4) n
O1 C1 C2 N1 162.5(3) n
O2 C1 C2 C3 103.2(4) n
O1 C1 C2 C3 -74.9(4) n
N1 C2 C3 C4 57.9(4) n
C1 C2 C3 C4 -63.9(3) n
C2 C3 C4 C5 178.5(3) n
C6 N2 C5 C4 -89.4(4) n
C3 C4 C5 N2 -67.5(4) n
C5 N2 C6 N4 4.4(6) n
C5 N2 C6 N3 -173.9(3) n
S1 O3 C7 C8 -178.3(5) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655615
