#------------------------------------------------------------------------------
#$Date: 2019-11-26 17:13:00 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243699 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/96/4089609.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_4089609
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         'C12 H10 N2 O6 W1'
_chemical_formula_sum            'C12 H10 N2 O6 W'
_chemical_formula_weight         462.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'intrinsic phasing'
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.4300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7582(4)
_cell_length_b                   6.8092(2)
_cell_length_c                   15.4418(4)
_cell_measurement_reflns_used    9718
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      42.27
_cell_measurement_theta_min      2.99
_cell_volume                     1446.17(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics
; ORTEP-3 for Windows (Farrugia, 1997),
 Mercury (Macrae et al., 2008)
_computing_publication_material   'SHELXL-2013'
;
_computing_structure_refinement  'SHELXTL-2013, SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker kappa Proton CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar multi-layer optics'
_diffrn_radiation_source         'I\ms micro focus'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            110276
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         42.611
_diffrn_reflns_theta_min         2.962
_exptl_absorpt_coefficient_mu    8.015
_exptl_absorpt_correction_T_max  0.7484
_exptl_absorpt_correction_T_min  0.3303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.174
_refine_diff_density_max         6.841
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         10419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0356P)²+1.0360P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0738
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9052
_reflns_number_total             10419
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om400778z_si_006.cif
_cod_data_source_block           compound_6
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C12 H10 N2 O6 W1'
_cod_database_code               4089609
_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. 
;
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.47984(14) -0.1742(3) 0.38955(12) 0.0273(3) Uani 1 1 d . .
C9 C 0.79388(17) -0.0263(4) 0.41671(18) 0.0317(4) Uani 1 1 d . .
H9 H 0.8585 0.0139 0.4174 0.038 Uiso 1 1 calc R U
C11 C 0.37855(18) -0.2231(5) 0.37505(17) 0.0367(5) Uani 1 1 d . .
H11A H 0.3659 -0.2512 0.3142 0.044 Uiso 1 1 calc R U
H11B H 0.3377 -0.1141 0.3918 0.044 Uiso 1 1 calc R U
N2 N 0.3902(2) -0.3690(4) 0.51800(15) 0.0376(4) Uani 1 1 d . .
C12 C 0.3567(2) -0.4038(5) 0.4299(2) 0.0390(5) Uani 1 1 d . .
H12A H 0.2873 -0.4293 0.4286 0.047 Uiso 1 1 calc R U
H12B H 0.3894 -0.5177 0.4067 0.047 Uiso 1 1 calc R U
H1 H 0.4831(18) -0.241(4) 0.4667(16) 0.008(5) Uiso 1 1 d . .
H2A H 0.350(3) -0.284(7) 0.539(3) 0.051(11) Uiso 1 1 d . .
H2B H 0.389(3) -0.499(8) 0.553(3) 0.051(11) Uiso 1 1 d . .
W1 W 0.49937(2) 0.05718(2) 0.21069(2) 0.01858(2) Uani 1 1 d . .
O4 O 0.58676(16) 0.4637(3) 0.27744(14) 0.0347(4) Uani 1 1 d . .
O5 O 0.70058(16) -0.0479(3) 0.12545(16) 0.0405(5) Uani 1 1 d . .
C4 C 0.55619(14) 0.3168(3) 0.25414(13) 0.0235(3) Uani 1 1 d . .
O6 O 0.65392(13) -0.1594(3) 0.45564(12) 0.0340(4) Uani 1 1 d . .
C8 C 0.72240(15) 0.0100(4) 0.34997(15) 0.0270(3) Uani 1 1 d . .
H8 H 0.7320 0.0772 0.2985 0.032 Uiso 1 1 calc R U
C2 C 0.44455(16) -0.2043(3) 0.16717(14) 0.0269(3) Uani 1 1 d . .
O2 O 0.41514(16) -0.3520(3) 0.14145(15) 0.0415(4) Uani 1 1 d . .
C6 C 0.53903(13) -0.0809(2) 0.33839(11) 0.0188(3) Uani 1 1 d . .
C3 C 0.36891(15) 0.1514(4) 0.25438(15) 0.0301(4) Uani 1 1 d . .
C7 C 0.63685(14) -0.0725(3) 0.37591(13) 0.0217(3) Uani 1 1 d . .
O1 O 0.4487(2) 0.2451(4) 0.02806(13) 0.0518(6) Uani 1 1 d . .
C10 C 0.74969(19) -0.1295(4) 0.47797(18) 0.0374(5) Uani 1 1 d . .
H10 H 0.7798 -0.1748 0.5287 0.045 Uiso 1 1 calc R U
O3 O 0.29668(15) 0.2161(4) 0.27657(16) 0.0490(5) Uani 1 1 d . .
C1 C 0.46636(19) 0.1790(4) 0.09510(14) 0.0308(4) Uani 1 1 d . .
C5 C 0.62868(15) -0.0154(3) 0.15865(14) 0.0250(3) Uani 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'
O O 0.0106 0.0060 '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
C6 N1 C11 128.96(18)
C6 N1 H1 136.7(11)
C11 N1 H1 94.2(11)
C10 C9 C8 106.5(2)
C10 C9 H9 126.7
C8 C9 H9 126.7
N1 C11 C12 107.6(2)
N1 C11 H11A 110.2
C12 C11 H11A 110.2
N1 C11 H11B 110.2
C12 C11 H11B 110.2
H11A C11 H11B 108.5
C12 N2 H2A 106(3)
C12 N2 H2B 110(3)
H2A N2 H2B 111(4)
N2 C12 C11 109.2(2)
N2 C12 H12A 109.8
C11 C12 H12A 109.8
N2 C12 H12B 109.8
C11 C12 H12B 109.8
H12A C12 H12B 108.3
C1 W1 C5 85.98(9)
C1 W1 C3 89.01(10)
C5 W1 C3 174.47(9)
C1 W1 C4 90.61(9)
C5 W1 C4 90.50(8)
C3 W1 C4 87.24(9)
C1 W1 C2 89.66(9)
C5 W1 C2 88.72(9)
C3 W1 C2 93.57(9)
C4 W1 C2 179.15(8)
C1 W1 C6 178.82(8)
C5 W1 C6 92.85(8)
C3 W1 C6 92.18(8)
C4 W1 C6 89.51(7)
C2 W1 C6 90.20(7)
O4 C4 W1 178.73(19)
C10 O6 C7 107.6(2)
C7 C8 C9 107.4(2)
C7 C8 H8 126.3
C9 C8 H8 126.3
O2 C2 W1 178.6(2)
N1 C6 C7 111.19(17)
N1 C6 W1 126.29(14)
C7 C6 W1 122.51(13)
O3 C3 W1 175.5(2)
C8 C7 O6 107.90(17)
C8 C7 C6 133.79(18)
O6 C7 C6 118.29(18)
C9 C10 O6 110.6(2)
C9 C10 H10 124.7
O6 C10 H10 124.7
O1 C1 W1 178.4(2)
O5 C5 W1 175.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.313(3)
N1 C11 1.445(3)
N1 H1 1.27(3)
C9 C10 1.337(4)
C9 C8 1.428(3)
C9 H9 0.9300
C11 C12 1.528(4)
C11 H11A 0.9700
C11 H11B 0.9700
N2 C12 1.444(4)
N2 H2A 0.87(4)
N2 H2B 1.04(5)
C12 H12A 0.9700
C12 H12B 0.9700
W1 C1 2.010(2)
W1 C5 2.031(2)
W1 C3 2.037(2)
W1 C4 2.040(2)
W1 C2 2.041(2)
W1 C6 2.2398(17)
O4 C4 1.140(3)
O5 C5 1.147(3)
O6 C10 1.369(3)
O6 C7 1.381(3)
C8 C7 1.373(3)
C8 H8 0.9300
C2 O2 1.151(3)
C6 C7 1.453(3)
C3 O3 1.147(3)
O1 C1 1.149(3)
C10 H10 0.9300
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 N1 C11 C12 154.2(2)
N1 C11 C12 N2 51.1(3)
C10 C9 C8 C7 0.9(3)
C11 N1 C6 C7 -176.6(2)
C11 N1 C6 W1 4.7(3)
C9 C8 C7 O6 -0.5(2)
C9 C8 C7 C6 178.1(2)
C10 O6 C7 C8 0.0(3)
C10 O6 C7 C6 -178.90(19)
N1 C6 C7 C8 -178.3(2)
W1 C6 C7 C8 0.4(3)
N1 C6 C7 O6 0.2(3)
W1 C6 C7 O6 178.97(14)
C8 C9 C10 O6 -1.0(3)
C7 O6 C10 C9 0.6(3)
