#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:11:15 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178939 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/68/4116833.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_4116833
loop_
_publ_author_name
'Miles P. Smith'
'Kenneth M. Johnson'
'Mei Zhang'
'Judith L. Flippen-Anderson'
'Alan P. Kozikowski'
_publ_section_title
;
 Tuning the Selectivity of Monoamine Transporter Inhibitors by the
 Stereochemistry of the Nitrogen Lone Pair
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9072
_journal_page_last               9073
_journal_paper_doi               10.1021/ja981423s
_journal_volume                  120
_journal_year                    1998
_chemical_formula_moiety         'C17 H22 N+ . C10 H15 S O4-'
_chemical_formula_sum            'C27 H37 N O4 S'
_chemical_formula_weight         471.64
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 104.35(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.629(2)
_cell_length_b                   10.343(2)
_cell_length_c                   14.836(3)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.59
_cell_measurement_theta_min      5.30
_cell_volume                     1282.8(5)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2298
_diffrn_reflns_theta_max         57.25
_diffrn_reflns_theta_min         3.07
_diffrn_standards_decay_%        1.2
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.374
_exptl_absorpt_correction_T_max  0.9279
_exptl_absorpt_correction_T_min  0.8037
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       rod
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.041
_refine_ls_goodness_of_fit_obs   1.064
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.048
_refine_ls_restrained_S_obs      1.072
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_obs          0.0696
_refine_ls_shift/esd_max         0.380
_refine_ls_shift/esd_mean        0.021
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1470P)²+0.5218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2110
_refine_ls_wR_factor_obs         0.1902
_reflns_number_observed          1510
_reflns_number_total             1865
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja981423s_2.cif
_cod_data_source_block           gu16z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1470P)^2^+0.5218P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1470P)^2^+0.5218P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1282.9(5)
_cod_database_code               4116833
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.1282(6) 0.3636(7) -0.4731(3) 0.082(2) Uani 1 d . .
H1A H 0.0253(6) 0.3654(7) -0.5080(3) 0.098 Uiso 1 calc R .
C2 C 0.2322(8) 0.2931(7) -0.5277(7) 0.103(3) Uani 1 d . .
H2A H 0.1853(8) 0.2121(7) -0.5565(7) 0.124 Uiso 1 calc R .
C3 C 0.2329(7) 0.4055(12) -0.6001(4) 0.096(3) Uani 1 d . .
H3A H 0.3312(7) 0.4050(12) -0.6207(4) 0.115 Uiso 1 calc R .
H3B H 0.1428(7) 0.3976(12) -0.6539(4) 0.115 Uiso 1 calc R .
C4 C 0.2204(10) 0.5225(10) -0.5475(7) 0.106(3) Uani 1 d . .
H4A H 0.3199(10) 0.5705(10) -0.5362(7) 0.127 Uiso 1 calc R .
H4B H 0.1356(10) 0.5771(10) -0.5831(7) 0.127 Uiso 1 calc R .
C5 C 0.1871(9) 0.4890(8) -0.4619(5) 0.081(2) Uani 1 d . .
H5A H 0.1100(9) 0.5487(8) -0.4458(5) 0.097 Uiso 1 calc R .
C6 C 0.3373(8) 0.4730(7) -0.3809(4) 0.074(2) Uani 1 d . .
H6A H 0.3770(8) 0.5546(7) -0.3501(4) 0.088 Uiso 1 calc R .
C7 C 0.2729(6) 0.3761(6) -0.3168(4) 0.0570(15) Uani 1 d . .
C8 C 0.1306(9) 0.3114(9) -0.3773(5) 0.088(2) Uani 1 d . .
H8A H 0.0337(9) 0.3343(9) -0.3591(5) 0.106 Uiso 1 calc R .
H8B H 0.1427(9) 0.2181(9) -0.3752(5) 0.106 Uiso 1 calc R .
C9 C 0.4017(8) 0.2760(7) -0.4599(5) 0.079(2) Uani 1 d . .
H9A H 0.3937(8) 0.2119(7) -0.4136(5) 0.094 Uiso 1 calc R .
H9B H 0.4733(8) 0.2418(7) -0.4951(5) 0.094 Uiso 1 calc R .
C10 C 0.4726(6) 0.3902(7) -0.4126(4) 0.0596(15) Uani 1 d . .
H10A H 0.5037(6) 0.4427(7) -0.4602(4) 0.071 Uiso 1 calc R .
C11 C 0.6214(6) 0.3798(6) -0.3342(4) 0.060(2) Uani 1 d . .
C12 C 0.6744(9) 0.2680(7) -0.2882(5) 0.079(2) Uani 1 d . .
H12A H 0.6209(9) 0.1915(7) -0.3090(5) 0.095 Uiso 1 calc R .
C13 C 0.8067(8) 0.2635(9) -0.2104(5) 0.084(2) Uani 1 d . .
H13A H 0.8397(8) 0.1852(9) -0.1811(5) 0.100 Uiso 1 calc R .
C14 C 0.8867(7) 0.3755(10) -0.1780(4) 0.082(2) Uani 1 d . .
C15 C 0.8371(10) 0.4853(11) -0.2259(7) 0.108(3) Uani 1 d . .
H15A H 0.8943(10) 0.5610(11) -0.2074(7) 0.129 Uiso 1 calc R .
C16 C 0.7084(9) 0.4906(9) -0.2994(6) 0.089(2) Uani 1 d . .
H16A H 0.6769(9) 0.5699(9) -0.3276(6) 0.107 Uiso 1 calc R .
C17 C 1.0233(8) 0.3769(14) -0.0904(6) 0.124(4) Uani 1 d . .
H17A H 1.0416(8) 0.2907(14) -0.0660(6) 0.186 Uiso 1 calc R .
H17B H 0.9957(8) 0.4321(14) -0.0447(6) 0.186 Uiso 1 calc R .
H17C H 1.1186(8) 0.4087(14) -0.1051(6) 0.186 Uiso 1 calc R .
C18 C 0.3258(9) 0.3604(8) -0.2281(4) 0.082(2) Uani 1 d . .
H18A H 0.2736(9) 0.3043(8) -0.1964(4) 0.098 Uiso 1 calc R .
H18B H 0.4160(9) 0.4052(8) -0.1959(4) 0.098 Uiso 1 calc R .
C1' C 0.7012(7) 0.3951(7) -0.8247(4) 0.065(2) Uani 1 d . .
C2' C 0.7269(11) 0.4830(8) -0.9050(5) 0.092(2) Uani 1 d . .
C3' C 0.6338(11) 0.4255(8) -0.9950(5) 0.094(3) Uani 1 d . .
H3'B H 0.7022(11) 0.4062(8) -1.0362(5) 0.113 Uiso 1 calc R .
H3'A H 0.5478(11) 0.4821(8) -1.0266(5) 0.113 Uiso 1 calc R .
C4' C 0.5678(10) 0.2988(7) -0.9595(4) 0.084(2) Uani 1 d . .
H4' H 0.4774(10) 0.2584(7) -1.0037(4) 0.101 Uiso 1 calc R .
C5' C 0.7134(12) 0.2132(8) -0.9266(6) 0.096(3) Uani 1 d . .
H5'B H 0.7767(12) 0.2108(8) -0.9722(6) 0.115 Uiso 1 calc R .
H5'A H 0.6820(12) 0.1257(8) -0.9155(6) 0.115 Uiso 1 calc R .
C7' C 0.5322(9) 0.3463(7) -0.8683(5) 0.073(2) Uani 1 d . .
C6' C 0.8087(11) 0.2769(8) -0.8347(5) 0.098(3) Uani 1 d . .
H6'B H 0.9137(11) 0.3046(8) -0.8395(5) 0.118 Uiso 1 calc R .
H6'A H 0.8205(11) 0.2180(8) -0.7825(5) 0.118 Uiso 1 calc R .
O4 O 0.8051(10) 0.5794(7) -0.8959(5) 0.142(3) Uani 1 d . .
C8' C 0.7485(10) 0.4702(7) -0.7348(4) 0.084(2) Uani 1 d . .
H8'B H 0.6803(10) 0.5460(7) -0.7420(4) 0.101 Uiso 1 calc R .
H8'A H 0.8568(10) 0.5010(7) -0.7287(4) 0.101 Uiso 1 calc R .
C9' C 0.4755(14) 0.2313(9) -0.8197(7) 0.120(3) Uani 1 d . .
H9'C H 0.5527(14) 0.1628(9) -0.8124(7) 0.180 Uiso 1 calc R .
H9'B H 0.3743(14) 0.2014(9) -0.8566(7) 0.180 Uiso 1 calc R .
H9'A H 0.4641(14) 0.2578(9) -0.7596(7) 0.180 Uiso 1 calc R .
C10' C 0.4095(11) 0.4530(10) -0.8792(6) 0.110(3) Uani 1 d . .
H10F H 0.3052(11) 0.4186(10) -0.9068(6) 0.165 Uiso 1 calc R .
H10E H 0.4343(11) 0.5195(10) -0.9186(6) 0.165 Uiso 1 calc R .
H10D H 0.4111(11) 0.4887(10) -0.8193(6) 0.165 Uiso 1 calc R .
S1 S 0.7434(2) 0.3970(2) -0.62711(9) 0.0699(4) Uani 1 d D .
O1 O 0.5815(6) 0.3923(16) -0.6303(4) 0.144(4) Uani 0.794(7) d PD 1
O2 O 0.8328(9) 0.2798(6) -0.6176(5) 0.078(2) Uani 0.794(7) d PD 1
O3 O 0.8344(8) 0.4949(7) -0.5599(4) 0.080(2) Uani 0.794(7) d PD 1
O1' O 0.5998(18) 0.3018(17) -0.6260(13) 0.055(5) Uiso 0.206(7) d PD 2
O3' O 0.7603(23) 0.4778(18) -0.5484(13) 0.060(6) Uiso 0.206(7) d PD 2
O2' O 0.8720(20) 0.3035(19) -0.6194(15) 0.044(6) Uiso 0.206(7) d PD 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C5 N1 C8 107.5(6)
C5 N1 C2 105.2(6)
C8 N1 C2 116.9(6)
N1 C2 C9 106.8(7)
N1 C2 C3 96.3(6)
C9 C2 C3 111.0(6)
C4 C3 C2 103.5(6)
C5 C4 C3 109.6(8)
N1 C5 C4 105.8(7)
N1 C5 C6 101.8(6)
C4 C5 C6 114.0(7)
C5 C6 C7 100.6(5)
C5 C6 C10 111.1(5)
C7 C6 C10 103.2(5)
C18 C7 C8 126.1(6)
C18 C7 C6 127.3(6)
C8 C7 C6 106.5(5)
C7 C8 N1 102.9(6)
C10 C9 C2 116.1(6)
C9 C10 C11 119.9(6)
C9 C10 C6 109.2(5)
C11 C10 C6 110.7(5)
C12 C11 C16 115.4(6)
C12 C11 C10 124.3(6)
C16 C11 C10 120.2(6)
C11 C12 C13 122.8(7)
C14 C13 C12 119.6(7)
C15 C14 C13 117.3(6)
C15 C14 C17 121.2(9)
C13 C14 C17 121.5(9)
C14 C15 C16 123.2(9)
C15 C16 C11 121.6(8)
C8' C1' C7' 124.4(6)
C8' C1' C2' 108.5(6)
C7' C1' C2' 99.9(5)
C8' C1' C6' 116.7(5)
C7' C1' C6' 103.2(6)
C2' C1' C6' 100.6(6)
O4 C2' C3' 126.6(8)
O4 C2' C1' 125.8(7)
C3' C2' C1' 107.6(6)
C2' C3' C4' 101.0(6)
C5' C4' C7' 103.5(6)
C5' C4' C3' 104.8(7)
C7' C4' C3' 101.3(6)
C4' C5' C6' 104.5(6)
C10' C7' C1' 112.0(6)
C10' C7' C9' 108.7(7)
C1' C7' C9' 116.1(7)
C10' C7' C4' 115.2(6)
C1' C7' C4' 95.7(6)
C9' C7' C4' 108.8(6)
C5' C6' C1' 102.5(6)
C1' C8' S1 120.9(5)
O1 S1 O2 119.3(7)
O3' S1 O2' 114.0(11)
O1 S1 O3 113.8(6)
O2 S1 O3 109.1(4)
O3' S1 O1' 106.2(10)
O2' S1 O1' 99.8(10)
O1 S1 C8' 103.5(5)
O3' S1 C8' 118.0(9)
O2 S1 C8' 108.5(4)
O2' S1 C8' 99.5(9)
O3 S1 C8' 100.6(4)
O1' S1 C8' 117.8(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.388(10)
N1 C8 1.516(9)
N1 C2 1.535(11)
C2 C9 1.566(9)
C2 C3 1.584(13)
C3 C4 1.459(14)
C4 C5 1.413(13)
C5 C6 1.543(9)
C6 C7 1.576(9)
C6 C10 1.609(9)
C7 C18 1.291(8)
C7 C8 1.488(9)
C9 C10 1.432(10)
C10 C11 1.507(7)
C11 C12 1.362(9)
C11 C16 1.397(10)
C12 C13 1.409(9)
C13 C14 1.373(12)
C14 C15 1.352(13)
C14 C17 1.524(9)
C15 C16 1.351(11)
C1' C8' 1.510(8)
C1' C7' 1.527(9)
C1' C2' 1.558(10)
C1' C6' 1.564(10)
C2' O4 1.193(10)
C2' C3' 1.499(10)
C3' C4' 1.571(12)
C4' C5' 1.515(11)
C4' C7' 1.540(10)
C5' C6' 1.554(11)
C7' C10' 1.510(11)
C7' C9' 1.532(12)
C8' S1 1.778(7)
S1 O1 1.387(6)
S1 O3' 1.41(2)
S1 O2 1.425(6)
S1 O2' 1.45(2)
S1 O3 1.500(6)
S1 O1' 1.585(15)
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
C5 N1 C2 C9 70.8(7)
C8 N1 C2 C9 -48.4(8)
C5 N1 C2 C3 -43.4(6)
C8 N1 C2 C3 -162.6(6)
N1 C2 C3 C4 30.4(6)
C9 C2 C3 C4 -80.3(8)
C2 C3 C4 C5 -9.4(8)
C8 N1 C5 C4 165.8(6)
C2 N1 C5 C4 40.6(7)
C8 N1 C5 C6 46.4(7)
C2 N1 C5 C6 -78.9(7)
C3 C4 C5 N1 -19.0(8)
C3 C4 C5 C6 92.1(8)
N1 C5 C6 C7 -40.3(7)
C4 C5 C6 C7 -153.7(7)
N1 C5 C6 C10 68.4(7)
C4 C5 C6 C10 -45.0(10)
C5 C6 C7 C18 -155.7(7)
C10 C6 C7 C18 89.5(8)
C5 C6 C7 C8 20.6(7)
C10 C6 C7 C8 -94.3(6)
C18 C7 C8 N1 -178.9(7)
C6 C7 C8 N1 4.8(7)
C5 N1 C8 C7 -32.7(7)
C2 N1 C8 C7 85.3(7)
N1 C2 C9 C10 -50.8(9)
C3 C2 C9 C10 53.1(10)
C2 C9 C10 C11 169.5(6)
C2 C9 C10 C6 40.3(8)
C5 C6 C10 C9 -48.2(8)
C7 C6 C10 C9 58.8(6)
C5 C6 C10 C11 177.7(6)
C7 C6 C10 C11 -75.3(6)
C9 C10 C11 C12 -17.0(9)
C6 C10 C11 C12 111.6(7)
C9 C10 C11 C16 167.9(7)
C6 C10 C11 C16 -63.5(8)
C16 C11 C12 C13 0.5(10)
C10 C11 C12 C13 -174.8(6)
C11 C12 C13 C14 0.5(12)
C12 C13 C14 C15 -2.7(11)
C12 C13 C14 C17 175.8(7)
C13 C14 C15 C16 4.1(14)
C17 C14 C15 C16 -174.4(8)
C14 C15 C16 C11 -3.3(15)
C12 C11 C16 C15 0.8(11)
C10 C11 C16 C15 176.3(8)
C8' C1' C2' O4 16.6(12)
C7' C1' C2' O4 148.1(10)
C6' C1' C2' O4 -106.4(10)
C8' C1' C2' C3' -162.6(6)
C7' C1' C2' C3' -31.1(8)
C6' C1' C2' C3' 74.5(7)
O4 C2' C3' C4' 177.1(10)
C1' C2' C3' C4' -3.7(8)
C2' C3' C4' C5' -70.2(7)
C2' C3' C4' C7' 37.2(8)
C7' C4' C5' C6' -33.2(8)
C3' C4' C5' C6' 72.6(8)
C8' C1' C7' C10' 52.7(9)
C2' C1' C7' C10' -67.9(7)
C6' C1' C7' C10' -171.3(7)
C8' C1' C7' C9' -72.9(9)
C2' C1' C7' C9' 166.5(7)
C6' C1' C7' C9' 63.0(8)
C8' C1' C7' C4' 172.9(6)
C2' C1' C7' C4' 52.3(6)
C6' C1' C7' C4' -51.2(6)
C5' C4' C7' C10' 169.6(7)
C3' C4' C7' C10' 61.3(8)
C5' C4' C7' C1' 52.1(7)
C3' C4' C7' C1' -56.3(6)
C5' C4' C7' C9' -68.0(8)
C3' C4' C7' C9' -176.4(7)
C4' C5' C6' C1' 0.7(9)
C8' C1' C6' C5' 172.3(7)
C7' C1' C6' C5' 32.3(8)
C2' C1' C6' C5' -70.6(7)
C7' C1' C8' S1 66.4(8)
C2' C1' C8' S1 -177.1(6)
C6' C1' C8' S1 -64.4(9)
C1' C8' S1 O1 -74.9(9)
C1' C8' S1 O3' -168.6(10)
C1' C8' S1 O2 52.8(7)
C1' C8' S1 O2' 67.5(10)
C1' C8' S1 O3 167.3(6)
C1' C8' S1 O1' -38.9(10)
