#------------------------------------------------------------------------------
#$Date: 2019-11-26 17:12:23 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243697 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/96/4089607.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_4089607
loop_
_publ_author_name
'Landman, Marilé'
'Pretorius, René'
'Buitendach, Blenerhassitt E.'
'van Rooyen, Petrus H.'
'Conradie, Jeanet'
_publ_section_title
;
 Synthesis, Structure, and Electrochemistry of Fischer Alkoxy- and
 Aminocarbene Complexes of Tungsten: The Use of DFT To Predict and
 Understand Oxidation and Reduction Potentials
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5491
_journal_paper_doi               10.1021/om400778z
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C16 H15 N O5 S W'
_chemical_formula_sum            'C16 H15 N O5 S W'
_chemical_formula_weight         517.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 112.472(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5736(8)
_cell_length_b                   9.6865(8)
_cell_length_c                   9.9936(8)
_cell_measurement_reflns_used    1862
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.51
_cell_volume                     856.38(12)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'Apex2 (Bruker, 2011)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2008)'
_computing_molecular_graphics
' ORTEP-3 for Windows (Farrugia, 1997), POV-Ray (Cason, 2004)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.4
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX DUO 4K-CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.404
_diffrn_reflns_theta_min         2.205
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    6.891
_exptl_absorpt_correction_T_max  0.475
_exptl_absorpt_correction_T_min  0.360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.006
_exptl_crystal_density_meas      ?
_exptl_crystal_description       bloc
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.709
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0165P)²] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0467
_refine_ls_wR_factor_ref         0.0480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2057
_reflns_number_total             2269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om400778z_si_004.cif
_cod_data_source_block           compound_3
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4089607
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.354
_shelx_estimated_absorpt_t_max   0.468
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
W1 W 0.54867(2) 0.2500 0.85643(2) 0.01164(6) Uani 1 2 d S T P . .
C1 C 0.4999(5) 0.2500 1.0346(5) 0.0189(11) Uani 1 2 d S T P . .
O1 O 0.4769(4) 0.2500 1.1398(4) 0.0277(9) Uani 1 2 d S T P . .
C2 C 0.3929(4) 0.4032(4) 0.7691(4) 0.0181(7) Uani 1 1 d . . . . .
O2 O 0.3071(3) 0.4893(3) 0.7234(3) 0.0254(6) Uani 1 1 d . . . . .
C4 C 0.7012(4) 0.0950(4) 0.9469(3) 0.0152(7) Uani 1 1 d . . . . .
O4 O 0.7824(3) 0.0064(3) 0.9992(3) 0.0246(6) Uani 1 1 d . . . . .
C6 C 0.6150(5) 0.2500 0.6614(5) 0.0121(9) Uani 1 2 d S T P A .
N1 N 0.5195(4) 0.2500 0.5237(4) 0.0148(8) Uani 1 2 d S T P . .
H1 H 0.5613 0.2500 0.4591 0.018 Uiso 1 2 calc R U P . .
C7 C 0.7740(5) 0.2500 0.6758(5) 0.0139(10) Uani 1 2 d DS T P . .
S1 S 0.8322(3) 0.2500 0.5349(5) 0.0219(8) Uani 0.564(6) 2 d DS T P A 1
C8 C 0.9064(13) 0.2500 0.8030(12) 0.008(3) Uiso 0.564(6) 2 d DS . P A 1
H8 H 0.9044 0.2500 0.8973 0.009 Uiso 0.564(6) 2 calc R U P A 1
S1A S 0.9142(5) 0.2500 0.8379(5) 0.0155(10) Uani 0.436(6) 2 d DS T P A 2
C8A C 0.8404(19) 0.2500 0.570(2) 0.040(10) Uiso 0.436(6) 2 d DS . P A 2
H8A H 0.7832 0.2500 0.4685 0.048 Uiso 0.436(6) 2 calc R U P A 2
C9 C 1.0460(6) 0.2500 0.7778(6) 0.0232(12) Uani 1 2 d DS T P . .
H9 H 1.1457 0.2500 0.8495 0.028 Uiso 1 2 calc R U P A 1
C10 C 1.0074(7) 0.2500 0.6345(6) 0.0325(14) Uani 1 2 d DS T P A .
H10 H 1.0820 0.2500 0.5934 0.039 Uiso 1 2 calc R U P B 1
C11 C 0.3558(5) 0.2500 0.4660(5) 0.0155(10) Uani 1 2 d S T P . .
H11 H 0.3207 0.2500 0.5482 0.019 Uiso 1 2 calc R U P . .
C12 C 0.2961(4) 0.3799(4) 0.3745(4) 0.0202(8) Uani 1 1 d . . . . .
H12A H 0.3334 0.4629 0.4355 0.024 Uiso 1 1 calc R U . . .
H12B H 0.3342 0.3830 0.2953 0.024 Uiso 1 1 calc R U . . .
C13 C 0.1236(4) 0.3799(4) 0.3104(4) 0.0228(8) Uani 1 1 d . . . . .
H13A H 0.0860 0.3864 0.3897 0.027 Uiso 1 1 calc R U . . .
H13B H 0.0869 0.4618 0.2475 0.027 Uiso 1 1 calc R U . . .
C14 C 0.0611(6) 0.2500 0.2227(6) 0.0268(13) Uani 1 2 d S T P . .
H14A H 0.0873 0.2500 0.1360 0.032 Uiso 1 2 calc R U P . .
H14B H -0.0504 0.2500 0.1895 0.032 Uiso 1 2 calc R U P . .
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'
W W -0.8490 6.8722 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 W1 C2 89.98(13) . .
C1 W1 C2 89.98(14) . 4_565
C2 W1 C2 92.91(19) . 4_565
C1 W1 C4 88.66(13) . 4_565
C2 W1 C4 86.38(13) . 4_565
C2 W1 C4 178.46(14) 4_565 4_565
C1 W1 C4 88.65(13) . .
C2 W1 C4 178.46(14) . .
C2 W1 C4 86.38(13) 4_565 .
C4 W1 C4 94.30(18) 4_565 .
C1 W1 C6 177.43(18) . .
C2 W1 C6 91.79(12) . .
C2 W1 C6 91.79(12) 4_565 .
C4 W1 C6 89.60(12) 4_565 .
C4 W1 C6 89.60(12) . .
O1 C1 W1 177.7(4) . .
O2 C2 W1 178.6(3) . .
O4 C4 W1 177.5(3) . .
N1 C6 C7 112.2(4) . .
N1 C6 W1 125.5(3) . .
C7 C6 W1 122.3(3) . .
C6 N1 C11 128.6(4) . .
C6 N1 H1 115.7 . .
C11 N1 H1 115.7 . .
C8 C7 C6 128.8(6) . .
C8A C7 C6 131.6(8) . .
C8A C7 S1A 107.4(8) . .
C6 C7 S1A 121.0(4) . .
C8 C7 S1 106.2(6) . .
C6 C7 S1 124.9(3) . .
C10 S1 C7 94.8(3) . .
C7 C8 C9 114.4(8) . .
C7 C8 H8 122.8 . .
C9 C8 H8 122.8 . .
C9 S1A C7 95.4(4) . .
C7 C8A C10 113.0(13) . .
C7 C8A H8A 123.5 . .
C10 C8A H8A 123.5 . .
C10 C9 C8 106.9(6) . .
C10 C9 S1A 118.1(5) . .
C10 C9 H9 126.6 . .
C8 C9 H9 126.6 . .
C9 C10 C8A 106.1(8) . .
C9 C10 S1 117.7(5) . .
C9 C10 H10 121.2 . .
S1 C10 H10 121.2 . .
N1 C11 C12 109.7(3) . .
N1 C11 C12 109.7(3) . 4_565
C12 C11 C12 110.4(4) . 4_565
N1 C11 H11 109.0 . .
C12 C11 H11 109.0 . .
C12 C11 H11 109.0 4_565 .
C13 C12 C11 110.3(3) . .
C13 C12 H12A 109.6 . .
C11 C12 H12A 109.6 . .
C13 C12 H12B 109.6 . .
C11 C12 H12B 109.6 . .
H12A C12 H12B 108.1 . .
C14 C13 C12 111.4(3) . .
C14 C13 H13A 109.3 . .
C12 C13 H13A 109.3 . .
C14 C13 H13B 109.3 . .
C12 C13 H13B 109.3 . .
H13A C13 H13B 108.0 . .
C13 C14 C13 111.8(4) . 4_565
C13 C14 H14A 109.3 . .
C13 C14 H14A 109.3 4_565 .
C13 C14 H14B 109.3 . .
C13 C14 H14B 109.3 4_565 .
H14A C14 H14B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
W1 C1 2.006(5) .
W1 C2 2.048(4) .
W1 C2 2.048(4) 4_565
W1 C4 2.048(4) 4_565
W1 C4 2.048(4) .
W1 C6 2.269(5) .
C1 O1 1.153(6) .
C2 O2 1.137(4) .
C4 O4 1.142(4) .
C6 N1 1.330(5) .
C6 C7 1.473(6) .
N1 C11 1.449(6) .
N1 H1 0.8800 .
C7 C8 1.411(12) .
C7 C8A 1.428(16) .
C7 S1A 1.663(6) .
C7 S1 1.701(6) .
S1 C10 1.590(7) .
C8 C9 1.451(12) .
C8 H8 0.9500 .
S1A C9 1.591(7) .
C8A C10 1.477(16) .
C8A H8A 0.9500 .
C9 C10 1.335(8) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C12 1.532(4) .
C11 C12 1.532(4) 4_565
C11 H11 1.0000 .
C12 C13 1.526(5) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.520(4) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C13 1.520(4) 4_565
C14 H14A 0.9900 .
C14 H14B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 S1 0.88 2.41 2.952(5) 120.4
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C7 C6 N1 C11 180.000(1) . .
W1 C6 N1 C11 0.000(2) . .
N1 C6 C7 C8 180.000(4) . .
W1 C6 C7 C8 0.000(4) . .
N1 C6 C7 C8A 0.000(5) . .
W1 C6 C7 C8A 180.000(5) . .
N1 C6 C7 S1A 180.000(2) . .
W1 C6 C7 S1A 0.000(2) . .
N1 C6 C7 S1 0.000(2) . .
W1 C6 C7 S1 180.000(1) . .
C8 C7 S1 C10 0.000(2) . .
C8A C7 S1 C10 0.000(9) . .
C6 C7 S1 C10 180.000(2) . .
S1A C7 S1 C10 0.000(2) . .
C8A C7 C8 C9 0.000(3) . .
C6 C7 C8 C9 180.000(2) . .
S1A C7 C8 C9 180.00(2) . .
S1 C7 C8 C9 0.000(3) . .
C8 C7 S1A C9 0.000(10) . .
C8A C7 S1A C9 0.000(2) . .
C6 C7 S1A C9 180.000(2) . .
S1 C7 S1A C9 0.000(2) . .
C8 C7 C8A C10 0.000(2) . .
C6 C7 C8A C10 180.000(3) . .
S1A C7 C8A C10 0.000(3) . .
S1 C7 C8A C10 180.00(3) . .
C7 C8 C9 C10 0.000(4) . .
C7 C8 C9 S1A 180.000(10) . .
C7 S1A C9 C10 0.000(2) . .
C7 S1A C9 C8 0.000(17) . .
C8 C9 C10 C8A 0.000(4) . .
S1A C9 C10 C8A 0.000(4) . .
C8 C9 C10 S1 0.000(2) . .
S1A C9 C10 S1 0.000(2) . .
C7 C8A C10 C9 0.000(5) . .
C7 C8A C10 S1 180.000(8) . .
C7 S1 C10 C9 0.000(2) . .
C7 S1 C10 C8A 0.000(19) . .
C6 N1 C11 C12 119.2(3) . .
C6 N1 C11 C12 -119.2(3) . 4_565
N1 C11 C12 C13 178.9(3) . .
C12 C11 C12 C13 57.8(5) 4_565 .
C11 C12 C13 C14 -56.0(4) . .
C12 C13 C14 C13 54.5(6) . 4_565
