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#$Date: 2016-03-21 10:21:50 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178647 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/58/4075836.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_4075836
loop_
_publ_author_name
'Wilton-Ely, James D. E. T.'
'Pogorzelec, Peter J.'
'Honarkhah, Sanaz J.'
'Reid, David H.'
'Tocher, Derek A.'
_publ_section_title
;
 Mixed-Donor Ligands:  Pyrrolecarbaldehyde and
 Pyrrolecarbothioaldehyde σ-Organyl Complexes of Ruthenium(II) and
 Osmium(II)
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              2862
_journal_paper_doi               10.1021/om050186g
_journal_volume                  24
_journal_year                    2005
_chemical_formula_sum            'C9 H13 N S'
_chemical_formula_weight         167.26
_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                 94.698(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9524(18)
_cell_length_b                   13.352(3)
_cell_length_c                   8.6274(19)
_cell_measurement_temperature    150(2)
_cell_volume                     913.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7759
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0590
_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)+(0.0614P)²+0.7386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1425
_reflns_number_gt                1697
_reflns_number_total             2172
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            om050186gsi20050314_010914.cif
_cod_data_source_block           strHL4
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4075836
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
S1 S 0.59482(9) 0.22091(5) 0.08824(7) 0.0284(2) Uani 1 1 d .
N1 N 0.6954(3) 0.42004(16) 0.2754(2) 0.0237(5) Uani 1 1 d .
C1 C 0.6480(3) 0.33299(19) 0.0257(3) 0.0250(5) Uani 1 1 d .
C2 C 0.6903(3) 0.41699(18) 0.1142(3) 0.0228(5) Uani 1 1 d .
C3 C 0.7315(3) 0.51441(19) 0.0658(3) 0.0244(5) Uani 1 1 d .
C4 C 0.7583(3) 0.57445(18) 0.1981(3) 0.0241(5) Uani 1 1 d .
C5 C 0.7352(3) 0.51259(18) 0.3266(3) 0.0232(5) Uani 1 1 d .
C6 C 0.7454(4) 0.5458(2) -0.0996(3) 0.0327(6) Uani 1 1 d .
H6A H 0.7748 0.6170 -0.1027 0.049 Uiso 1 1 calc R
H6B H 0.6371 0.5348 -0.1600 0.049 Uiso 1 1 calc R
H6C H 0.8332 0.5062 -0.1443 0.049 Uiso 1 1 calc R
C7 C 0.8009(3) 0.68358(19) 0.2051(3) 0.0287(6) Uani 1 1 d .
H7A H 0.7768 0.7098 0.3083 0.034 Uiso 1 1 calc R
H7B H 0.7267 0.7193 0.1257 0.034 Uiso 1 1 calc R
C8 C 0.9822(4) 0.7065(2) 0.1789(5) 0.0537(9) Uani 1 1 d .
H8A H 1.0009 0.7790 0.1856 0.081 Uiso 1 1 calc R
H8B H 1.0066 0.6828 0.0756 0.081 Uiso 1 1 calc R
H8C H 1.0570 0.6727 0.2583 0.081 Uiso 1 1 calc R
C9 C 0.7529(4) 0.5374(2) 0.4955(3) 0.0319(6) Uani 1 1 d .
H9A H 0.7289 0.4777 0.5560 0.048 Uiso 1 1 calc R
H9B H 0.6733 0.5907 0.5167 0.048 Uiso 1 1 calc R
H9C H 0.8684 0.5601 0.5249 0.048 Uiso 1 1 calc R
H1 H 0.669(4) 0.371(2) 0.332(3) 0.027(7) Uiso 1 1 d .
H2 H 0.648(4) 0.344(2) -0.084(3) 0.032(8) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0346(4) 0.0231(3) 0.0273(3) -0.0035(3) 0.0010(3) -0.0030(3)
N1 0.0307(12) 0.0210(11) 0.0196(10) -0.0001(8) 0.0032(9) 0.0005(8)
C1 0.0251(13) 0.0274(14) 0.0228(12) -0.0012(10) 0.0038(10) 0.0010(10)
C2 0.0243(12) 0.0238(12) 0.0202(11) -0.0003(9) 0.0013(9) 0.0036(9)
C3 0.0237(12) 0.0249(13) 0.0247(12) 0.0019(10) 0.0028(10) 0.0029(10)
C4 0.0238(12) 0.0207(12) 0.0278(13) 0.0000(10) 0.0031(10) 0.0017(9)
C5 0.0254(12) 0.0210(12) 0.0231(12) -0.0018(10) 0.0006(10) 0.0021(9)
C6 0.0398(16) 0.0323(15) 0.0271(14) 0.0047(11) 0.0092(12) 0.0015(12)
C7 0.0309(14) 0.0206(12) 0.0349(14) 0.0005(11) 0.0039(11) -0.0001(10)
C8 0.0320(17) 0.0352(18) 0.094(3) -0.0016(18) 0.0037(17) -0.0069(13)
C9 0.0431(16) 0.0269(14) 0.0254(13) -0.0038(11) 0.0013(12) 0.0015(11)
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
C5 N1 C2 110.1(2)
C2 C1 S1 127.6(2)
C1 C2 N1 124.2(2)
C1 C2 C3 129.4(2)
N1 C2 C3 106.3(2)
C4 C3 C2 108.1(2)
C4 C3 C6 126.8(2)
C2 C3 C6 125.1(2)
C3 C4 C5 106.6(2)
C3 C4 C7 127.7(2)
C5 C4 C7 125.7(2)
N1 C5 C4 108.9(2)
N1 C5 C9 121.9(2)
C4 C5 C9 129.2(2)
C4 C7 C8 114.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.657(3)
N1 C5 1.342(3)
N1 C2 1.388(3)
C1 C2 1.383(3)
C2 C3 1.413(3)
C3 C4 1.397(3)
C3 C6 1.500(3)
C4 C5 1.407(3)
C4 C7 1.496(4)
C5 C9 1.489(3)
C7 C8 1.509(4)
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
S1 C1 C2 N1 0.2(4)
S1 C1 C2 C3 -177.9(2)
C5 N1 C2 C1 -178.0(2)
C5 N1 C2 C3 0.5(3)
C1 C2 C3 C4 177.7(2)
N1 C2 C3 C4 -0.8(3)
C1 C2 C3 C6 -3.0(4)
N1 C2 C3 C6 178.6(2)
C2 C3 C4 C5 0.7(3)
C6 C3 C4 C5 -178.6(2)
C2 C3 C4 C7 -178.5(2)
C6 C3 C4 C7 2.2(4)
C2 N1 C5 C4 -0.1(3)
C2 N1 C5 C9 -178.8(2)
C3 C4 C5 N1 -0.4(3)
C7 C4 C5 N1 178.8(2)
C3 C4 C5 C9 178.2(2)
C7 C4 C5 C9 -2.6(4)
C3 C4 C7 C8 -76.2(4)
C5 C4 C7 C8 104.7(3)
