#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/22/4112227.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_4112227
loop_
_publ_author_name
'D. Leusser'
'J. Henn'
'N. Kocher'
'B. Engels'
'D. Stalke'
_publ_contact_author             'Prof. Dr. Dietmar Stalke'
_publ_contact_author_email       dstalke@chemie.uni-wuerzburg.de
_publ_section_title
;
 SN versus S+N-: An Experimental and Theoretical Charge Density Study
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1781
_journal_page_last               1793
_journal_paper_doi               10.1021/ja038941+
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C9 H22 N2 S'
_chemical_formula_weight         190.35
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.8510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8832(3)
_cell_length_b                   14.7504(5)
_cell_length_c                   9.3656(3)
_cell_measurement_reflns_used    7321
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.45
_cell_volume                     1146.81(7)
_computing_cell_refinement       'SAINT-NT V5/6.0'
_computing_data_collection       'SMART-NT V5.6'
_computing_data_reduction        'SAINT-NT V5/6.0'
_computing_molecular_graphics    'SHELXTL-NT V5.1'
_computing_publication_material  'SHELXTL-NT V5.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker Smart Apex with D8-Goniometer '
_diffrn_measurement_method       'omega scan'
_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
'0.05677 (low angle batch), 0.0300 (high angle batch)'
_diffrn_reflns_av_sigmaI/netI
'0.0133 (low angle batch), 0.0392 (high angle batch)'
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number
'54868 (low angle batch), 42875 (high angle batch)'
_diffrn_reflns_theta_full        54.06
_diffrn_reflns_theta_max         54.06
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'MULABS implemented in PLATON'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_description       blocks
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         14000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0691
_reflns_number_gt                10668
_reflns_number_total             14000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0389412Bsi20031008_100518.cif
_cod_data_source_block           sulfin
_cod_database_code               4112227
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
S1 S 0.394847(8) 0.028146(4) 0.175902(7) 0.01290(2) Uani 1 1 d
N1 N 0.58629(3) 0.056874(15) 0.20283(2) 0.01413(3) Uani 1 1 d
H1 H 0.6330(9) 0.0228(4) 0.1539(8) 0.017 Uiso 1 1 d
N2 N 0.28219(3) 0.049521(15) 0.00552(2) 0.01421(3) Uani 1 1 d
C3 C 0.40250(4) -0.093011(18) 0.16712(4) 0.01899(4) Uani 1 1 d
H2 H 0.4289(9) -0.1063(6) 0.0834(9) 0.028 Uiso 1 1 d
H3 H 0.3011(10) -0.1143(5) 0.1607(9) 0.028 Uiso 1 1 d
H4 H 0.4806(10) -0.1159(5) 0.2618(9) 0.028 Uiso 1 1 d
C1 C 0.69724(3) 0.082097(17) 0.35782(3) 0.01518(3) Uani 1 1 d
C11 C 0.85120(4) 0.11447(3) 0.33661(5) 0.02399(5) Uani 1 1 d
H11 H 0.8270(11) 0.1644(6) 0.2690(10) 0.036 Uiso 1 1 d
H12 H 0.9330(11) 0.1347(6) 0.4374(10) 0.036 Uiso 1 1 d
H13 H 0.8964(10) 0.0663(6) 0.2913(10) 0.036 Uiso 1 1 d
C12 C 0.73494(4) 0.00182(2) 0.46875(3) 0.02112(5) Uani 1 1 d
H14 H 0.8096(11) 0.0171(6) 0.5587(10) 0.032 Uiso 1 1 d
H15 H 0.7797(11) -0.0495(5) 0.4330(10) 0.032 Uiso 1 1 d
H16 H 0.6373(11) -0.0198(5) 0.4888(10) 0.032 Uiso 1 1 d
C13 C 0.62546(5) 0.15952(2) 0.42126(4) 0.02302(5) Uani 1 1 d
H17 H 0.5281(10) 0.1420(6) 0.4362(9) 0.035 Uiso 1 1 d
H18 H 0.5999(10) 0.2123(6) 0.3539(10) 0.035 Uiso 1 1 d
H19 H 0.7040(10) 0.1794(6) 0.5207(10) 0.035 Uiso 1 1 d
C2 C 0.18567(3) 0.134158(16) -0.01428(3) 0.01440(3) Uani 1 1 d
C21 C 0.07145(6) 0.13226(3) -0.18029(4) 0.02765(7) Uani 1 1 d
H21 H 0.0079(11) 0.0792(7) -0.2046(10) 0.041 Uiso 1 1 d
H22 H 0.0005(11) 0.1877(6) -0.2055(10) 0.041 Uiso 1 1 d
H23 H 0.1319(12) 0.1341(6) -0.2477(11) 0.041 Uiso 1 1 d
C22 C 0.08330(5) 0.13636(2) 0.08738(5) 0.02314(5) Uani 1 1 d
H24 H 0.0137(10) 0.1902(6) 0.0673(10) 0.035 Uiso 1 1 d
H25 H 0.0113(10) 0.0848(6) 0.0702(10) 0.035 Uiso 1 1 d
H26 H 0.1495(10) 0.1381(6) 0.1919(10) 0.035 Uiso 1 1 d
C23 C 0.28970(5) 0.21943(2) 0.01342(7) 0.02910(8) Uani 1 1 d
H27 H 0.3649(12) 0.2252(7) 0.1193(11) 0.044 Uiso 1 1 d
H28 H 0.3548(11) 0.2198(6) -0.0457(11) 0.044 Uiso 1 1 d
H29 H 0.2248(11) 0.2740(6) -0.0127(11) 0.044 Uiso 1 1 d
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'
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
N2 S1 N1 110.079(12)
N2 S1 C3 99.960(13)
N1 S1 C3 101.847(13)
C1 N1 S1 119.620(17)
C1 N1 H1 112.5(5)
S1 N1 H1 114.7(5)
C2 N2 S1 114.947(17)
S1 C3 H2 106.2(5)
S1 C3 H3 106.7(5)
H2 C3 H3 114.0(7)
S1 C3 H4 109.4(4)
H2 C3 H4 112.9(7)
H3 C3 H4 107.5(7)
N1 C1 C11 105.38(2)
N1 C1 C13 110.14(2)
C11 C1 C13 109.51(3)
N1 C1 C12 112.25(2)
C11 C1 C12 109.90(3)
C13 C1 C12 109.56(3)
C1 C11 H11 109.3(5)
C1 C11 H12 110.5(5)
H11 C11 H12 108.2(7)
C1 C11 H13 110.6(5)
H11 C11 H13 107.7(7)
H12 C11 H13 110.4(7)
C1 C12 H14 110.7(5)
C1 C12 H15 112.8(5)
H14 C12 H15 105.3(7)
C1 C12 H16 112.2(5)
H14 C12 H16 107.7(7)
H15 C12 H16 107.7(7)
C1 C13 H17 112.2(5)
C1 C13 H18 112.2(5)
H17 C13 H18 107.2(7)
C1 C13 H19 109.6(5)
H17 C13 H19 108.3(7)
H18 C13 H19 107.2(7)
N2 C2 C21 104.86(2)
N2 C2 C23 112.51(2)
C21 C2 C23 109.34(3)
N2 C2 C22 112.52(2)
C21 C2 C22 107.88(3)
C23 C2 C22 109.50(3)
C2 C21 H21 112.6(5)
C2 C21 H22 111.0(5)
H21 C21 H22 110.2(8)
C2 C21 H23 110.1(6)
H21 C21 H23 106.9(8)
H22 C21 H23 105.7(7)
C2 C22 H24 111.7(5)
C2 C22 H25 112.5(5)
H24 C22 H25 105.6(7)
C2 C22 H26 110.9(5)
H24 C22 H26 107.0(7)
H25 C22 H26 108.9(7)
C2 C23 H27 113.3(6)
C2 C23 H28 111.7(6)
H27 C23 H28 104.9(8)
C2 C23 H29 111.8(6)
H27 C23 H29 108.2(8)
H28 C23 H29 106.5(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 N2 1.5844(2)
S1 N1 1.6823(2)
S1 C3 1.7914(3)
N1 C1 1.4827(3)
N1 H1 0.877(7)
N2 C2 1.4882(3)
C3 H2 0.915(8)
C3 H3 0.935(8)
C3 H4 0.971(8)
C1 C11 1.5269(4)
C1 C13 1.5276(4)
C1 C12 1.5316(4)
C11 H11 0.944(9)
C11 H12 1.010(9)
C11 H13 0.984(9)
C12 H14 0.896(9)
C12 H15 0.969(8)
C12 H16 1.003(9)
C13 H17 0.960(9)
C13 H18 0.976(9)
C13 H19 0.989(8)
C2 C21 1.5247(4)
C2 C23 1.5273(4)
C2 C22 1.5333(4)
C21 H21 0.945(10)
C21 H22 1.008(9)
C21 H23 0.964(10)
C22 H24 0.983(8)
C22 H25 0.969(9)
C22 H26 0.946(9)
C23 H27 0.982(10)
C23 H28 0.932(10)
C23 H29 0.969(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28557517
