#------------------------------------------------------------------------------
#$Date: 2013-12-28 14:58:47 +0100 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/04/2100478.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_2100478
loop_
_publ_author_name
'Edwin A Collier'
'Roger J Davey'
'Simon N Black'
'Ronald J Roberts'
_publ_section_title
;
 17 salts of ephedrine: crystal structures and packing analysis
;
_journal_coeditor_code           BK5025
_journal_date_accepted           2006-04-03
_journal_date_recd_electronic    2005-10-17
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              498
_journal_page_last               505
_journal_paper_category          FA
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C17 H23 N1 O7 S1'
_chemical_formula_structural     'C17 H23 N1 O7 S1'
_chemical_formula_sum            'C17 H23 N O4 S'
_chemical_formula_weight         337.42
_chemical_name_systematic
;
(1R, 2S)-(-)-ephedrine P-tosylate
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7491(2)
_cell_length_b                   7.1665(2)
_cell_length_c                   42.0343(9)
_cell_measurement_reflns_used    19550
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1731.85(9)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.934
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            6102
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.88
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.022
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.286
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.06
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.3943P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0993
_reflns_number_gt                2839
_reflns_number_total             3446
_reflns_threshold_expression     >2sigma(I)
_[local]_cod_data_source_file    bk5025.cif
_[local]_cod_data_source_block   EPHETOSY
_cod_database_code               2100478
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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 0 '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 0.006 '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_
_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
C C1 -0.0136(5) 0.8334(3) 0.30748(7) 0.0388(6) Uani d . 1
H H1 0.115(5) 0.827(4) 0.3222(7) 0.047 Uiso d . 1
C C2 0.0202(5) 0.9236(4) 0.27872(8) 0.0518(8) Uani d . 1
H H2 0.169(5) 0.992(4) 0.2735(7) 0.062 Uiso d . 1
C C3 -0.1510(6) 0.9211(4) 0.25576(8) 0.0591(9) Uani d . 1
H H3 -0.121(5) 0.975(5) 0.2342(8) 0.071 Uiso d . 1
C C4 -0.3549(5) 0.8292(5) 0.26177(8) 0.0562(8) Uani d . 1
H H4 -0.475(6) 0.819(4) 0.2464(8) 0.067 Uiso d . 1
C C5 -0.3920(5) 0.7377(4) 0.29042(7) 0.0442(7) Uani d . 1
H H5 -0.548(5) 0.679(4) 0.2963(7) 0.053 Uiso d . 1
C C6 -0.2218(4) 0.7413(3) 0.31369(6) 0.0320(5) Uani d . 1
C C7 -0.2538(4) 0.6446(3) 0.34531(6) 0.0304(5) Uani d . 1
H H7 -0.177(4) 0.711(3) 0.3607(6) 0.036 Uiso d . 1
C C8 -0.1373(4) 0.4527(4) 0.34526(6) 0.0333(5) Uani d . 1
H H8 0.041(4) 0.475(4) 0.3419(6) 0.04 Uiso d . 1
C C9 -0.2427(6) 0.3176(4) 0.32176(7) 0.0500(8) Uani d . 1
H H9A -0.217(5) 0.350(4) 0.3018(8) 0.06 Uiso d . 1
H H9B -0.422(5) 0.315(4) 0.3240(7) 0.06 Uiso d . 1
H H9C -0.182(5) 0.202(5) 0.3240(7) 0.06 Uiso d . 1
C C10 -0.0726(6) 0.4751(5) 0.40487(7) 0.0498(7) Uani d . 1
H H12A -0.171(5) 0.587(4) 0.4090(7) 0.06 Uiso d . 1
H H12B 0.085(5) 0.526(4) 0.3995(7) 0.06 Uiso d . 1
H H12C -0.061(5) 0.394(4) 0.4221(8) 0.06 Uiso d . 1
C C11 0.2059(5) 1.0550(3) 0.49750(6) 0.0355(5) Uani d . 1
H H13 0.293(4) 1.090(3) 0.5165(7) 0.043 Uiso d . 1
C C12 0.2979(4) 1.0796(3) 0.46741(6) 0.0301(5) Uani d . 1
H H14 0.438(4) 1.125(3) 0.4643(6) 0.036 Uiso d . 1
C C13 0.1744(3) 1.0255(3) 0.44070(5) 0.0267(5) Uani d . 1
H H15 -0.149(4) 0.920(3) 0.4274(6) 0.032 Uiso d . 1
C C14 -0.0465(4) 0.9489(3) 0.44428(6) 0.0334(5) Uani d . 1
H H16 -0.292(4) 0.871(3) 0.4783(6) 0.04 Uiso d . 1
C C15 -0.1348(4) 0.9222(3) 0.47470(7) 0.0378(6) Uani d . 1
C C16 -0.0119(4) 0.9739(3) 0.50166(6) 0.0351(5) Uani d . 1
C C17 -0.1153(5) 0.9427(4) 0.53420(7) 0.0519(7) Uani d . 1
H H17A -0.2793 0.9204 0.5322 0.078 Uiso calc R 1
H H17B -0.0899 1.0513 0.5471 0.078 Uiso calc R 1
H H17C -0.0425 0.8367 0.544 0.078 Uiso calc R 1
N N1 -0.1613(3) 0.3644(3) 0.37777(5) 0.0349(5) Uani d . 1
H H10 -0.3129 0.3405 0.3812 0.042 Uiso calc R 1
H H11 -0.0863 0.2543 0.3775 0.042 Uiso calc R 1
O O1 -0.4928(3) 0.6161(2) 0.35346(4) 0.0382(4) Uani d . 1
H H6 -0.534(5) 0.695(4) 0.3661(7) 0.046 Uiso d . 1
O O2 0.4535(3) 0.8834(3) 0.39905(5) 0.0478(5) Uani d . 1
O O3 0.4268(4) 1.2203(3) 0.40278(5) 0.0573(6) Uani d . 1
O O4 0.1095(3) 1.0419(3) 0.37990(4) 0.0461(5) Uani d . 1
S S1 0.30178(10) 1.04466(8) 0.402484(15) 0.03374(16) Uani 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
C1 0.0416(13) 0.0321(13) 0.0426(17) 0.0031(12) 0.0055(13) 0.0019(11)
C2 0.0579(16) 0.0393(15) 0.058(2) 0.0061(15) 0.0222(16) 0.0111(13)
C3 0.079(2) 0.0553(19) 0.0435(18) 0.0280(17) 0.0236(17) 0.0177(15)
C4 0.062(2) 0.073(2) 0.0341(19) 0.0215(17) -0.0028(15) 0.0088(15)
C5 0.0445(14) 0.0526(17) 0.0355(17) 0.0096(13) -0.0018(12) 0.0034(13)
C6 0.0379(12) 0.0260(11) 0.0323(14) 0.0072(10) 0.0035(11) -0.0016(9)
C7 0.0301(12) 0.0299(12) 0.0313(14) 0.0007(9) 0.0012(10) -0.0037(10)
C8 0.0382(12) 0.0346(12) 0.0270(13) 0.0076(11) 0.0016(10) 0.0020(11)
C9 0.080(2) 0.0324(14) 0.0375(18) 0.0119(15) -0.0018(16) -0.0062(12)
C10 0.0728(19) 0.0456(15) 0.0309(16) 0.0020(15) -0.0108(15) -0.0025(14)
C11 0.0462(12) 0.0275(11) 0.0327(14) -0.0035(12) -0.0027(11) -0.0013(10)
C12 0.0275(10) 0.0280(12) 0.0347(13) -0.0006(10) -0.0009(11) 0.0004(9)
C13 0.0284(10) 0.0218(10) 0.0300(13) 0.0027(10) 0.0015(9) 0.0003(9)
C14 0.0305(11) 0.0272(12) 0.0425(16) 0.0012(11) -0.0070(10) -0.0010(11)
C15 0.0291(11) 0.0267(13) 0.0576(19) -0.0019(10) 0.0089(11) 0.0031(11)
C16 0.0456(12) 0.0216(10) 0.0381(15) 0.0072(11) 0.0115(11) 0.0005(10)
C17 0.0703(17) 0.0332(13) 0.0523(19) -0.0018(14) 0.0284(15) 0.0006(13)
N1 0.0404(11) 0.0317(10) 0.0326(12) 0.0076(9) 0.0010(9) 0.0025(9)
O1 0.0350(8) 0.0360(9) 0.0436(12) 0.0049(8) 0.0108(8) -0.0023(8)
O2 0.0477(10) 0.0600(11) 0.0355(11) 0.0235(9) 0.0003(9) -0.0105(9)
O3 0.0794(14) 0.0495(11) 0.0431(13) -0.0265(10) 0.0230(12) -0.0051(10)
O4 0.0562(10) 0.0489(10) 0.0333(11) 0.0124(10) -0.0097(8) -0.0019(9)
S1 0.0385(3) 0.0334(3) 0.0293(3) 0.0025(3) 0.0023(3) -0.0027(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.385(4)
C1 C6 1.392(3)
C1 H1 0.96(3)
C2 C3 1.379(5)
C2 H2 1.01(3)
C3 C4 1.368(4)
C3 H3 1.00(3)
C4 C5 1.388(4)
C4 H4 0.95(3)
C5 C6 1.383(4)
C5 H5 1.02(3)
C6 C7 1.510(3)
C7 O1 1.430(3)
C7 C8 1.530(3)
C7 H7 0.92(3)
C8 C9 1.510(4)
C8 N1 1.512(3)
C8 H8 1.05(2)
C9 H9A 0.89(3)
C9 H9B 1.03(3)
C9 H9C 0.91(3)
C10 N1 1.479(3)
C10 H12A 1.00(3)
C10 H12B 1.00(3)
C10 H12C 0.93(3)
C11 C12 1.383(3)
C11 C16 1.391(4)
C11 H13 0.98(3)
C12 C13 1.384(3)
C12 H14 0.88(2)
C13 C14 1.392(3)
C13 S1 1.771(2)
C14 C15 1.389(4)
C14 H15 0.94(2)
C15 C16 1.386(4)
C15 H16 0.99(3)
C16 C17 1.508(3)
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
N1 H10 0.9
N1 H11 0.9
O1 H6 0.81(3)
O2 S1 1.4547(17)
O3 S1 1.4496(19)
O4 S1 1.4572(18)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 120.4(3)
C2 C1 H1 118.2(17)
C6 C1 H1 121.2(17)
C3 C2 C1 120.3(3)
C3 C2 H2 117.4(17)
C1 C2 H2 122.3(18)
C4 C3 C2 119.3(3)
C4 C3 H3 120.2(18)
C2 C3 H3 120.2(17)
C3 C4 C5 121.3(3)
C3 C4 H4 122(2)
C5 C4 H4 116(2)
C6 C5 C4 119.7(3)
C6 C5 H5 117.3(16)
C4 C5 H5 122.6(16)
C5 C6 C1 119.0(2)
C5 C6 C7 121.8(2)
C1 C6 C7 119.2(2)
O1 C7 C6 113.15(19)
O1 C7 C8 107.02(19)
C6 C7 C8 110.97(19)
O1 C7 H7 111.6(16)
C6 C7 H7 108.8(16)
C8 C7 H7 105.0(15)
C9 C8 N1 106.6(2)
C9 C8 C7 113.7(2)
N1 C8 C7 109.55(19)
C9 C8 H8 113.6(15)
N1 C8 H8 106.0(15)
C7 C8 H8 107.1(15)
C8 C9 H9A 113(2)
C8 C9 H9B 110.6(17)
H9A C9 H9B 105(3)
C8 C9 H9C 112(2)
H9A C9 H9C 106(3)
H9B C9 H9C 111(3)
N1 C10 H12A 111.5(17)
N1 C10 H12B 109.5(18)
H12A C10 H12B 105(2)
N1 C10 H12C 106.8(19)
H12A C10 H12C 114(3)
H12B C10 H12C 110(2)
C12 C11 C16 120.8(2)
C12 C11 H13 121.4(16)
C16 C11 H13 117.7(15)
C11 C12 C13 120.7(2)
C11 C12 H14 122.2(17)
C13 C12 H14 117.0(16)
C12 C13 C14 119.4(2)
C12 C13 S1 120.15(17)
C14 C13 S1 120.41(18)
C15 C14 C13 119.2(2)
C15 C14 H15 115.7(15)
C13 C14 H15 125.0(15)
C16 C15 C14 122.0(2)
C16 C15 H16 116.2(16)
C14 C15 H16 121.8(16)
C15 C16 C11 117.9(2)
C15 C16 C17 120.1(2)
C11 C16 C17 122.0(2)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C10 N1 C8 116.1(2)
C10 N1 H10 108.3
C8 N1 H10 108.3
C10 N1 H11 108.3
C8 N1 H11 108.3
H10 N1 H11 107.4
C7 O1 H6 110(2)
O3 S1 O2 113.17(12)
O3 S1 O4 113.18(13)
O2 S1 O4 112.29(11)
O3 S1 C13 105.33(11)
O2 S1 C13 106.04(11)
O4 S1 C13 106.03(11)
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
C6 C1 C2 C3 -0.8(4)
C1 C2 C3 C4 0.3(5)
C2 C3 C4 C5 -0.4(5)
C3 C4 C5 C6 1.0(5)
C4 C5 C6 C1 -1.5(4)
C4 C5 C6 C7 179.8(2)
C2 C1 C6 C5 1.4(4)
C2 C1 C6 C7 -179.8(2)
C5 C6 C7 O1 -22.8(3)
C1 C6 C7 O1 158.5(2)
C5 C6 C7 C8 97.5(3)
C1 C6 C7 C8 -81.2(3)
O1 C7 C8 C9 60.0(3)
C6 C7 C8 C9 -63.9(3)
O1 C7 C8 N1 -59.2(2)
C6 C7 C8 N1 176.94(18)
C16 C11 C12 C13 0.5(3)
C11 C12 C13 C14 1.2(3)
C11 C12 C13 S1 -176.11(17)
C12 C13 C14 C15 -2.3(3)
S1 C13 C14 C15 175.04(18)
C13 C14 C15 C16 1.7(3)
C14 C15 C16 C11 0.1(3)
C14 C15 C16 C17 179.8(2)
C12 C11 C16 C15 -1.2(3)
C12 C11 C16 C17 179.1(2)
C9 C8 N1 C10 -178.9(2)
C7 C8 N1 C10 -55.5(3)
C12 C13 S1 O3 -40.2(2)
C14 C13 S1 O3 142.52(19)
C12 C13 S1 O2 80.06(19)
C14 C13 S1 O2 -97.26(19)
C12 C13 S1 O4 -160.39(17)
C14 C13 S1 O4 22.3(2)
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 H11 O4 1_545 0.9 1.9 2.789(2) 171.4
N1 H11 S1 1_545 0.9 2.89 3.663(2) 145.4
N1 H10 O3 1_445 0.9 1.95 2.789(3) 154.4
O1 H6 O2 1_455 0.81(3) 1.94(3) 2.727(2) 165(3)
_journal_paper_doi 10.1107/S0108768106012018