#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/30/1513059.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_1513059
loop_
_publ_author_name
'Ivanova, Bojidarka'
'Spiteller, Michael'
_publ_section_title
;
 Factors stabilizing the gas-phase ionic species of crystals of organic
 salts – Experimental and theoretical study
;
_journal_name_full               'Journal of Molecular Structure'
_journal_page_first              226
_journal_paper_doi               10.1016/j.molstruc.2012.11.018
_journal_volume                  1036
_journal_year                    2013
_chemical_formula_moiety         'C13 H18 Cl N O6 S'
_chemical_formula_sum            'C13 H18 Cl N O6 S'
_chemical_formula_weight         351.79
_chemical_melting_point          317
_chemical_name_common
'1-(2-chloroethyl)pyrrolidinium 5-sulfosalicylicilate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.782(8)
_cell_angle_beta                 104.882(9)
_cell_angle_gamma                105.085(8)
_cell_formula_units_Z            2
_cell_length_a                   8.644(2)
_cell_length_b                   9.085(3)
_cell_length_c                   11.673(4)
_cell_measurement_temperature    291(2)
_cell_volume                     802.9(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker GIS'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1699
_diffrn_reflns_av_sigmaI/netI    0.1124
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7702
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.8642
_exptl_absorpt_correction_T_min  0.8231
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.37
_refine_diff_density_max         1.837
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.027(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.547
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.547
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0851
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1040P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2578
_refine_ls_wR_factor_ref         0.2666
_reflns_number_gt                2307
_reflns_number_total             2821
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Struct-200-22.cif
_cod_data_source_block           200-22
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '317K' was changed to '317' - the
value should be numeric and without a unit
designator.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               1513059
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.05923(11) 0.71255(13) 0.76768(8) 0.0364(4) Uani 1 1 d .
O6 O -0.7352(4) 0.3561(4) 0.6071(3) 0.0565(9) Uani 1 1 d .
O5 O 0.0318(3) 0.8156(4) 0.8712(2) 0.0415(7) Uani 1 1 d .
C13 C -0.1397(5) 0.5557(5) 0.6788(3) 0.0304(9) Uani 1 1 d .
C12 C -0.2837(5) 0.5694(5) 0.7016(3) 0.0304(8) Uani 1 1 d .
H12 H -0.2760 0.6624 0.7626 0.036 Uiso 1 1 calc R
O4 O -0.5688(4) 0.5970(4) 0.7479(3) 0.0541(9) Uani 1 1 d .
H4 H -0.6514 0.6262 0.7306 0.081 Uiso 1 1 calc R
C11 C -0.1516(5) 0.4169(5) 0.5867(4) 0.0401(10) Uani 1 1 d .
H11 H -0.0541 0.4078 0.5702 0.048 Uiso 1 1 calc R
O3 O -0.6024(4) 0.1845(4) 0.4756(3) 0.0611(10) Uani 1 1 d .
H3 H -0.5971 0.1014 0.4890 0.092 Uiso 1 1 calc R
O2 O 0.1739(4) 0.6328(4) 0.8123(3) 0.0569(9) Uani 1 1 d .
C10 C -0.4527(5) 0.3071(6) 0.5437(4) 0.0432(10) Uani 1 1 d .
C9 C -0.4415(5) 0.4464(5) 0.6349(3) 0.0334(9) Uani 1 1 d .
C8 C -0.5965(5) 0.4625(6) 0.6616(4) 0.0392(10) Uani 1 1 d .
C7 C -0.3048(6) 0.2942(6) 0.5203(4) 0.0446(11) Uani 1 1 d .
H7 H -0.3111 0.2017 0.4594 0.053 Uiso 1 1 calc R
O1 O 0.1087(5) 0.7963(4) 0.6860(3) 0.0670(11) Uani 1 1 d .
Cl1 Cl 0.23493(16) 0.30059(19) 0.96371(12) 0.0657(5) Uani 1 1 d .
N1 N -0.1699(4) 0.1485(4) 0.8753(3) 0.0389(9) Uani 1 1 d .
H1 H -0.0968 0.1772 0.9554 0.047 Uiso 1 1 calc R
C6 C -0.0780(6) 0.1087(6) 0.7859(4) 0.0519(12) Uani 1 1 d .
H6A H -0.1543 0.0809 0.7004 0.062 Uiso 1 1 calc R
H6B H -0.0494 0.0138 0.7918 0.062 Uiso 1 1 calc R
C5 C -0.3247(7) 0.0029(6) 0.8520(5) 0.0628(14) Uani 1 1 d .
H5A H -0.3649 -0.0724 0.7661 0.075 Uiso 1 1 calc R
H5B H -0.2976 -0.0540 0.9101 0.075 Uiso 1 1 calc R
C4 C -0.2346(6) 0.2849(6) 0.8664(5) 0.0563(12) Uani 1 1 d .
H4A H -0.1779 0.3775 0.9443 0.068 Uiso 1 1 calc R
H4B H -0.2158 0.3187 0.7973 0.068 Uiso 1 1 calc R
C3 C 0.0834(6) 0.2449(7) 0.8100(5) 0.0601(13) Uani 1 1 d .
H3A H 0.0550 0.3387 0.8008 0.072 Uiso 1 1 calc R
H3B H 0.1341 0.2113 0.7473 0.072 Uiso 1 1 calc R
C2 C -0.4191(9) 0.2163(11) 0.8438(10) 0.109(3) Uani 1 1 d .
H2A H -0.4534 0.2946 0.8956 0.131 Uiso 1 1 calc R
H2B H -0.4843 0.1917 0.7558 0.131 Uiso 1 1 calc R
C1 C -0.4518(9) 0.0737(11) 0.8741(9) 0.113(3) Uani 1 1 d .
H1A H -0.5658 -0.0019 0.8216 0.136 Uiso 1 1 calc R
H1B H -0.4436 0.0990 0.9619 0.136 Uiso 1 1 calc 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O5 S1 O2 111.08(18)
O5 S1 O1 112.5(2)
O2 S1 O1 113.6(2)
O5 S1 C13 105.75(16)
O2 S1 C13 105.4(2)
O1 S1 C13 107.91(18)
C12 C13 C11 119.5(4)
C12 C13 S1 119.7(3)
C11 C13 S1 120.8(3)
C13 C12 C9 121.0(4)
C7 C11 C13 120.6(4)
O3 C10 C9 122.0(4)
O3 C10 C7 118.7(4)
C9 C10 C7 119.3(4)
C12 C9 C10 119.4(3)
C12 C9 C8 120.3(4)
C10 C9 C8 120.3(4)
O6 C8 O4 124.0(4)
O6 C8 C9 121.9(4)
O4 C8 C9 114.1(4)
C11 C7 C10 120.1(4)
C6 N1 C4 113.7(3)
C6 N1 C5 111.5(4)
C4 N1 C5 106.4(4)
N1 C6 C3 113.9(4)
C1 C5 N1 104.0(4)
C2 C4 N1 104.6(5)
C6 C3 Cl1 112.1(3)
C1 C2 C4 108.9(5)
C2 C1 C5 107.3(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.442(3)
S1 O2 1.442(3)
S1 O1 1.443(3)
S1 C13 1.766(4)
O6 C8 1.211(5)
C13 C12 1.367(5)
C13 C11 1.394(6)
C12 C9 1.390(5)
O4 C8 1.288(5)
C11 C7 1.364(6)
O3 C10 1.348(5)
C10 C9 1.393(6)
C10 C7 1.401(6)
C9 C8 1.486(5)
Cl1 C3 1.782(5)
N1 C6 1.494(5)
N1 C4 1.501(6)
N1 C5 1.525(5)
C6 C3 1.509(7)
C5 C1 1.455(8)
C4 C2 1.478(8)
C2 C1 1.407(11)
