#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/99/1519963.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_1519963
loop_
_publ_author_name
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 Ethanol-2-ammonium naphthalenesulphonate
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              567
_journal_year                    2008
_chemical_formula_sum            'C12 H15 N O4 S'
_chemical_formula_weight         269.31
_chemical_name_systematic
;
Ethanol-2-ammonium naphthalenesulphonate
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.361(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7465(12)
_cell_length_b                   8.6976(8)
_cell_length_c                   10.3290(6)
_cell_measurement_reflns_used    2904
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1224.77(17)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1299
_diffrn_reflns_av_sigmaI/netI    0.1129
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14900
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.9973
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1242
_refine_ls_R_factor_gt           0.0661
_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)+(0.0348P)²+0.9572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                1790
_reflns_number_total             2804
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-567.cif
_cod_data_source_block           06skc0022p21c
_cod_depositor_comments
;
Citation :
Callear, Samantha K. and Hursthouse, Michael B. (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/567)

More at:
http://ecrystals.chem.soton.ac.uk/567/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1519963
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8617(2) 0.0757(4) 0.1538(3) 0.0166(7) Uani 1 1 d . . .
H1 H 0.8463 -0.0038 0.2108 0.020 Uiso 1 1 calc R . .
C2 C 0.7883(2) 0.1628(3) 0.0887(3) 0.0145(7) Uani 1 1 d . . .
C3 C 0.8089(2) 0.2800(4) 0.0009(3) 0.0193(7) Uani 1 1 d . . .
H3 H 0.7572 0.3380 -0.0454 0.023 Uiso 1 1 calc R . .
C4 C 0.9043(2) 0.3085(4) -0.0162(3) 0.0195(7) Uani 1 1 d . . .
H4 H 0.9181 0.3872 -0.0751 0.023 Uiso 1 1 calc R . .
C5 C 0.9828(2) 0.2242(4) 0.0512(3) 0.0179(7) Uani 1 1 d . . .
C6 C 1.0821(2) 0.2550(4) 0.0392(3) 0.0229(8) Uani 1 1 d . . .
H6 H 1.0977 0.3343 -0.0179 0.027 Uiso 1 1 calc R . .
C7 C 1.1561(3) 0.1730(4) 0.1080(3) 0.0247(8) Uani 1 1 d . . .
H7 H 1.2225 0.1978 0.1007 0.030 Uiso 1 1 calc R . .
C8 C 1.1342(3) 0.0513(4) 0.1900(3) 0.0234(8) Uani 1 1 d . . .
H8 H 1.1859 -0.0073 0.2359 0.028 Uiso 1 1 calc R . .
C9 C 1.0390(2) 0.0175(4) 0.2038(3) 0.0207(7) Uani 1 1 d . . .
H9 H 1.0249 -0.0647 0.2590 0.025 Uiso 1 1 calc R . .
C10 C 0.9612(2) 0.1037(4) 0.1364(3) 0.0161(7) Uani 1 1 d . . .
O2A O 0.61832(16) 0.0568(3) -0.0072(2) 0.0230(5) Uani 1 1 d . . .
O2B O 0.66502(16) 0.0310(3) 0.2258(2) 0.0242(6) Uani 1 1 d . . .
O2C O 0.62349(16) 0.2820(3) 0.1302(2) 0.0263(6) Uani 1 1 d . . .
S2 S 0.66515(6) 0.13067(9) 0.11268(7) 0.0182(2) Uani 1 1 d . . .
C22 C 1.3576(2) 0.1626(4) 0.4268(3) 0.0202(7) Uani 1 1 d . . .
H22A H 1.3035 0.2211 0.3768 0.024 Uiso 1 1 calc R . .
H22B H 1.3315 0.0611 0.4487 0.024 Uiso 1 1 calc R . .
C23 C 1.4389(2) 0.1399(4) 0.3430(3) 0.0205(7) Uani 1 1 d . . .
H23A H 1.4914 0.0760 0.3907 0.025 Uiso 1 1 calc R . .
H23B H 1.4129 0.0847 0.2621 0.025 Uiso 1 1 calc R . .
N24 N 1.48093(19) 0.2912(3) 0.3084(2) 0.0189(6) Uani 1 1 d . . .
H24A H 1.5186 0.3304 0.3796 0.028 Uiso 1 1 calc R . .
H24B H 1.4313 0.3577 0.2818 0.028 Uiso 1 1 calc R . .
H24C H 1.5184 0.2774 0.2428 0.028 Uiso 1 1 calc R . .
O21 O 1.39078(17) 0.2428(3) 0.54390(19) 0.0223(5) Uani 1 1 d . . .
H21 H 1.3896 0.3378 0.5293 0.033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C10 120.3(3) . .
C2 C1 H1 119.8 . .
C10 C1 H1 119.8 . .
C1 C2 C3 121.1(3) . .
C1 C2 S2 120.3(2) . .
C3 C2 S2 118.6(2) . .
C4 C3 C2 119.2(3) . .
C4 C3 H3 120.4 . .
C2 C3 H3 120.4 . .
C3 C4 C5 121.7(3) . .
C3 C4 H4 119.1 . .
C5 C4 H4 119.1 . .
C6 C5 C4 123.0(3) . .
C6 C5 C10 118.3(3) . .
C4 C5 C10 118.8(3) . .
C7 C6 C5 121.3(3) . .
C7 C6 H6 119.4 . .
C5 C6 H6 119.4 . .
C6 C7 C8 120.2(3) . .
C6 C7 H7 119.9 . .
C8 C7 H7 119.9 . .
C9 C8 C7 120.3(3) . .
C9 C8 H8 119.9 . .
C7 C8 H8 119.9 . .
C8 C9 C10 120.6(3) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C9 C10 C1 121.7(3) . .
C9 C10 C5 119.4(3) . .
C1 C10 C5 118.9(3) . .
O2B S2 O2C 113.44(14) . .
O2B S2 O2A 111.77(14) . .
O2C S2 O2A 111.32(14) . .
O2B S2 C2 107.87(14) . .
O2C S2 C2 105.91(14) . .
O2A S2 C2 106.01(13) . .
O21 C22 C23 111.8(3) . .
O21 C22 H22A 109.3 . .
C23 C22 H22A 109.3 . .
O21 C22 H22B 109.3 . .
C23 C22 H22B 109.3 . .
H22A C22 H22B 107.9 . .
N24 C23 C22 110.9(3) . .
N24 C23 H23A 109.5 . .
C22 C23 H23A 109.5 . .
N24 C23 H23B 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 108.0 . .
C23 N24 H24A 109.5 . .
C23 N24 H24B 109.5 . .
H24A N24 H24B 109.5 . .
C23 N24 H24C 109.5 . .
H24A N24 H24C 109.5 . .
H24B N24 H24C 109.5 . .
C22 O21 H21 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.368(4) .
C1 C10 1.423(4) .
C1 H1 0.9500 .
C2 C3 1.417(4) .
C2 S2 1.764(3) .
C3 C4 1.368(4) .
C3 H3 0.9500 .
C4 C5 1.412(4) .
C4 H4 0.9500 .
C5 C6 1.412(4) .
C5 C10 1.424(4) .
C6 C7 1.365(5) .
C6 H6 0.9500 .
C7 C8 1.412(5) .
C7 H7 0.9500 .
C8 C9 1.367(5) .
C8 H8 0.9500 .
C9 C10 1.413(4) .
C9 H9 0.9500 .
O2A S2 1.469(2) .
O2B S2 1.455(2) .
O2C S2 1.456(2) .
C22 O21 1.420(4) .
C22 C23 1.512(4) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 N24 1.499(4) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
N24 H24A 0.9100 .
N24 H24B 0.9100 .
N24 H24C 0.9100 .
O21 H21 0.8400 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N24 H24A O2A 0.91 1.95 2.832(3) 163.2 4_666
N24 H24A S2 0.91 2.95 3.836(3) 163.7 4_666
N24 H24B O2B 0.91 2.00 2.884(3) 163.2 2_755
N24 H24B S2 0.91 2.99 3.719(3) 138.1 2_755
O21 H21 O2A 0.84 1.92 2.758(3) 175.6 2_755
O21 H21 S2 0.84 2.99 3.778(2) 157.7 2_755
N24 H24C O2C 0.91 1.97 2.856(3) 165.0 1_655
N24 H24C S2 0.91 2.86 3.710(3) 155.3 1_655
