#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/01/2230125.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_2230125
loop_
_publ_author_name
'Zhang, Lijun'
'Di, Youying'
'Dan, Wenyan'
_publ_section_title
;
 Pentadecylammonium methyl sulfate
;
_journal_coeditor_code           RU2002
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1051
_journal_paper_doi               10.1107/S1600536811011226
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H34 N +, C H3 O4 S -'
_chemical_formula_moiety         'C15 H34 N +, C H3 O4 S -'
_chemical_formula_sum            'C16 H37 N O4 S'
_chemical_formula_weight         339.53
_chemical_name_systematic
;
Pentadecylammonium methyl sulfate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_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                 93.5570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.4260(5)
_cell_length_b                   7.4981(6)
_cell_length_c                   24.376(2)
_cell_measurement_reflns_used    823
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.512
_cell_volume                     989.82(15)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_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      298(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0621
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5243
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9514
_exptl_absorpt_correction_T_min  0.9464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0742
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1131P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2054
_refine_ls_wR_factor_ref         0.2281
_reflns_number_gt                1025
_reflns_number_total             1880
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ru2002.cif
_cod_data_source_block           I
_cod_original_cell_volume        989.83(15)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2230125
_cod_database_fobs_code          2230125
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.3365(3) 0.7500 0.07723(6) 0.0623(6) Uani d S 1 . .
O O1 0.3834(8) 0.7500 0.14136(16) 0.0806(13) Uani d S 1 . .
O O2 0.0747(8) 0.7500 0.07105(18) 0.1042(16) Uani d S 1 . .
O O3 0.4507(5) 0.5923(3) 0.05732(12) 0.0784(10) Uani d . 1 . .
N N1 1.2215(8) 0.2500 0.03004(18) 0.0562(12) Uani d S 1 . .
H H1A 1.1749 0.2500 -0.0056 0.084 Uiso d SR 1 . .
H H1B 1.3113 0.3469 0.0381 0.084 Uiso d R 1 . .
C C1 0.9998(10) 0.2500 0.0626(2) 0.0559(14) Uani d S 1 . .
H H1 0.9012 0.3544 0.0527 0.067 Uiso d R 1 . .
C C2 1.0542(10) 0.2500 0.1226(2) 0.0582(14) Uani d S 1 . .
H H2 1.1521 0.3545 0.1327 0.070 Uiso d R 1 . .
C C3 0.8258(10) 0.2500 0.1545(2) 0.0601(14) Uani d S 1 . .
H H3 0.7285 0.3543 0.1437 0.072 Uiso d R 1 . .
C C4 0.8663(11) 0.2500 0.2159(2) 0.0702(16) Uani d S 1 . .
H H4 0.9641 0.3542 0.2265 0.084 Uiso d R 1 . .
C C5 0.6433(11) 0.2500 0.2481(2) 0.0720(17) Uani d S 1 . .
H H5 0.5458 0.3541 0.2374 0.086 Uiso d R 1 . .
C C6 0.6793(13) 0.2500 0.3087(3) 0.087(2) Uani d S 1 . .
H H6 0.7782 0.3539 0.3190 0.104 Uiso d R 1 . .
C C7 0.4670(12) 0.2500 0.3429(2) 0.0811(19) Uani d S 1 . .
H H7 0.3682 0.3538 0.3325 0.097 Uiso d R 1 . .
C C8 0.5000(14) 0.2500 0.4025(3) 0.098(2) Uani d S 1 . .
H H8 0.5995 0.3537 0.4127 0.117 Uiso d R 1 . .
C C9 0.2936(12) 0.2500 0.4378(2) 0.085(2) Uani d S 1 . .
H H9 0.1941 0.3538 0.4277 0.102 Uiso d R 1 . .
C C10 0.3271(14) 0.2500 0.4972(3) 0.101(2) Uani d S 1 . .
H H10 0.4269 0.3537 0.5072 0.122 Uiso d R 1 . .
C C11 0.1238(13) 0.2500 0.5329(3) 0.089(2) Uani d S 1 . .
H H11 0.0241 0.3537 0.5228 0.106 Uiso d R 1 . .
C C12 0.1563(14) 0.2500 0.5919(3) 0.106(2) Uani d S 1 . .
H H12 0.2565 0.3536 0.6018 0.127 Uiso d R 1 . .
C C13 -0.0447(14) 0.2500 0.6282(3) 0.092(2) Uani d S 1 . .
H H13 -0.1449 0.3536 0.6184 0.111 Uiso d R 1 . .
C C14 -0.0117(16) 0.2500 0.6873(3) 0.116(3) Uani d S 1 . .
H H14 0.0882 0.3537 0.6973 0.139 Uiso d R 1 . .
C C15 -0.2143(16) 0.2500 0.7228(3) 0.113(3) Uani d S 1 . .
H H15C -0.1514 0.2500 0.7605 0.169 Uiso d SR 1 . .
H H15D -0.3134 0.3545 0.7157 0.169 Uiso d R 1 . .
C C16 0.6344(14) 0.7500 0.1633(3) 0.096(2) Uani d S 1 . .
H H16A 0.6379 0.7500 0.2028 0.144 Uiso d SR 1 . .
H H16B 0.7168 0.8545 0.1510 0.144 Uiso d 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 . 4_575 114.50(15) ?
O2 S1 O3 . . 114.50(15) ?
O3 S1 O3 4_575 . 111.2(2) ?
O2 S1 O1 . . 101.8(3) ?
O3 S1 O1 4_575 . 106.91(15) ?
O3 S1 O1 . . 106.91(15) ?
C16 O1 S1 . . 117.7(4) ?
C1 N1 H1A . . 109.4 ?
C1 N1 H1B . . 109.5 ?
H1A N1 H1B . . 109.5 ?
C2 C1 N1 . . 114.3(4) ?
C2 C1 H1 . . 108.6 ?
N1 C1 H1 . . 108.7 ?
C1 C2 C3 . . 113.1(4) ?
C1 C2 H2 . . 109.0 ?
C3 C2 H2 . . 108.9 ?
C4 C3 C2 . . 116.2(5) ?
C4 C3 H3 . . 108.3 ?
C2 C3 H3 . . 108.2 ?
C5 C4 C3 . . 117.0(5) ?
C5 C4 H4 . . 108.0 ?
C3 C4 H4 . . 108.0 ?
C6 C5 C4 . . 117.9(5) ?
C6 C5 H5 . . 107.8 ?
C4 C5 H5 . . 107.8 ?
C7 C6 C5 . . 120.6(6) ?
C7 C6 H6 . . 107.2 ?
C5 C6 H6 . . 107.2 ?
C8 C7 C6 . . 121.1(6) ?
C8 C7 H7 . . 107.0 ?
C6 C7 H7 . . 107.1 ?
C7 C8 C9 . . 122.7(7) ?
C7 C8 H8 . . 106.7 ?
C9 C8 H8 . . 106.6 ?
C10 C9 C8 . . 122.6(6) ?
C10 C9 H9 . . 106.7 ?
C8 C9 H9 . . 106.7 ?
C11 C10 C9 . . 123.2(7) ?
C11 C10 H10 . . 106.5 ?
C9 C10 H10 . . 106.5 ?
C12 C11 C10 . . 123.4(7) ?
C12 C11 H11 . . 106.5 ?
C10 C11 H11 . . 106.4 ?
C11 C12 C13 . . 124.2(7) ?
C11 C12 H12 . . 106.3 ?
C13 C12 H12 . . 106.3 ?
C14 C13 C12 . . 124.1(7) ?
C14 C13 H13 . . 106.3 ?
C12 C13 H13 . . 106.3 ?
C13 C14 C15 . . 123.2(8) ?
C13 C14 H14 . . 106.5 ?
C15 C14 H14 . . 106.5 ?
C14 C15 H15C . . 109.6 ?
C14 C15 H15D . . 109.4 ?
H15C C15 H15D . . 109.5 ?
O1 C16 H16A . . 109.5 ?
O1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
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
S1 O2 . 1.419(5) ?
S1 O3 4_575 1.434(3) ?
S1 O3 . 1.434(3) ?
S1 O1 . 1.568(4) ?
O1 C16 . 1.432(8) ?
N1 C1 . 1.481(6) ?
N1 H1A . 0.8900 ?
N1 H1B . 0.8900 ?
C1 C2 . 1.474(7) ?
C1 H1 . 0.9700 ?
C2 C3 . 1.503(7) ?
C2 H2 . 0.9700 ?
C3 C4 . 1.500(7) ?
C3 H3 . 0.9700 ?
C4 C5 . 1.483(7) ?
C4 H4 . 0.9700 ?
C5 C6 . 1.478(8) ?
C5 H5 . 0.9700 ?
C6 C7 . 1.462(8) ?
C6 H6 . 0.9700 ?
C7 C8 . 1.453(8) ?
C7 H7 . 0.9700 ?
C8 C9 . 1.454(8) ?
C8 H8 . 0.9700 ?
C9 C10 . 1.450(8) ?
C9 H9 . 0.9700 ?
C10 C11 . 1.445(8) ?
C10 H10 . 0.9700 ?
C11 C12 . 1.439(9) ?
C11 H11 . 0.9700 ?
C12 C13 . 1.447(9) ?
C12 H12 . 0.9700 ?
C13 C14 . 1.440(8) ?
C13 H13 . 0.9700 ?
C14 C15 . 1.441(9) ?
C14 H14 . 0.9700 ?
C15 H15C . 0.9600 ?
C15 H15D . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
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 O2 3_665 0.89 2.03 2.857(6) 154.7
N1 H1B O3 1_655 0.89 2.03 2.911(3) 168.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 O1 C16 . . . . 180.0000(10) ?
O3 S1 O1 C16 4_575 . . . -59.57(14) ?
O3 S1 O1 C16 . . . . 59.57(14) ?
N1 C1 C2 C3 . . . . 180.0 ?
C1 C2 C3 C4 . . . . 180.0000(10) ?
C2 C3 C4 C5 . . . . 180.0000(10) ?
C3 C4 C5 C6 . . . . 180.000(2) ?
C4 C5 C6 C7 . . . . 180.000(2) ?
C5 C6 C7 C8 . . . . 180.000(3) ?
C6 C7 C8 C9 . . . . 180.000(3) ?
C7 C8 C9 C10 . . . . 180.000(4) ?
C8 C9 C10 C11 . . . . 180.000(3) ?
C9 C10 C11 C12 . . . . 180.000(4) ?
C10 C11 C12 C13 . . . . 180.000(5) ?
C11 C12 C13 C14 . . . . 180.000(6) ?
C12 C13 C14 C15 . . . . 180.000(6) ?
