#------------------------------------------------------------------------------
#$Date: 2016-03-23 01:58:35 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179164 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/25/4312558.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_4312558
loop_
_publ_author_name
'David V. Partyka'
'Richard J. Staples'
'R. H. Holm'
_publ_section_title
;
 Nucleophilic Reactivity and Oxo/Sulfido Substitution Reactions of MVIO3
 Groups (M = Mo, W)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7877
_journal_page_last               7886
_journal_paper_doi               10.1021/ic030185l
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C10 H22 F3 Mo N3 O6 S'
_chemical_formula_weight         465.31
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.03(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7008(15)
_cell_length_b                   15.198(3)
_cell_length_c                   14.866(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1735.6(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11767
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.442
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7543
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.442
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          13.412
_refine_ls_shift/su_mean         0.724
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0728P)²+20.1768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0779
_reflns_number_gt                7370
_reflns_number_total             7543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic030185l_03.cif
_cod_data_source_block           Compound4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4312558
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mo1 Mo 0.58990(4) 0.48917(2) 0.49857(2) 0.02452(7) Uani 1 1 d . . .
Mo2 Mo 0.36531(4) 0.51140(2) -0.02897(2) 0.02888(9) Uani 1 1 d . . .
S2 S 0.82313(13) 0.69261(7) 0.25632(7) 0.0295(2) Uani 1 1 d . . .
O2 O 0.8007(4) 0.4955(3) 0.5396(2) 0.0431(7) Uani 1 1 d . . .
S1 S 0.04566(15) 0.73257(8) 0.76652(7) 0.0350(2) Uani 1 1 d . . .
N1 N 0.5185(4) 0.4797(2) 0.6451(2) 0.0283(7) Uani 1 1 d . . .
N3 N 0.2886(4) 0.5116(2) 0.49367(19) 0.0230(6) Uani 1 1 d . . .
O5 O 0.3394(4) 0.4749(3) -0.1370(2) 0.0446(8) Uani 1 1 d . . .
O3 O 0.5425(5) 0.3800(2) 0.4870(3) 0.0444(8) Uani 1 1 d . . .
O1 O 0.5824(4) 0.5331(2) 0.38066(19) 0.0392(7) Uani 1 1 d . . .
N5 N 0.3195(4) 0.5160(2) 0.1243(2) 0.0275(6) Uani 1 1 d . . .
F8 F 0.3188(4) 0.8097(2) 0.7061(2) 0.0558(8) Uani 1 1 d . . .
F6 F 0.9950(4) 0.8406(2) 0.2682(2) 0.0518(8) Uani 1 1 d . . .
O4 O 0.2980(5) 0.6297(2) -0.0305(2) 0.0443(8) Uani 1 1 d . . .
N6 N 0.0746(4) 0.4713(2) -0.0169(2) 0.0308(8) Uani 1 1 d . . .
O10 O 0.6732(4) 0.7402(2) 0.2805(3) 0.0461(8) Uani 1 1 d . . .
O11 O 0.8509(4) 0.6098(2) 0.3037(2) 0.0399(7) Uani 1 1 d . . .
C20 C 1.0041(6) 0.7591(3) 0.3028(3) 0.0362(9) Uani 1 1 d . . .
F4 F 1.0034(4) 0.7685(2) 0.3913(2) 0.0537(8) Uani 1 1 d . . .
O7 O -0.1351(5) 0.7563(3) 0.7595(3) 0.0547(10) Uani 1 1 d . . .
N2 N 0.5482(4) 0.6347(2) 0.5463(2) 0.0270(7) Uani 1 1 d . . .
O8 O 0.1292(5) 0.7442(3) 0.8560(2) 0.0500(9) Uani 1 1 d . . .
O9 O 0.0890(6) 0.6532(2) 0.7218(3) 0.0534(9) Uani 1 1 d . . .
C1 C 0.5948(6) 0.5585(3) 0.6920(3) 0.0394(10) Uani 1 1 d . . .
H1A H 0.7208 0.5559 0.6927 0.047 Uiso 1 1 calc R . .
H1B H 0.5628 0.5591 0.7539 0.047 Uiso 1 1 calc R . .
O6 O 0.5829(4) 0.5118(3) -0.0014(2) 0.0528(11) Uani 1 1 d . . .
F5 F 1.1556(4) 0.7247(2) 0.2856(3) 0.0580(9) Uani 1 1 d . . .
F7 F 0.0896(5) 0.8148(3) 0.6156(2) 0.0629(9) Uani 1 1 d . . .
C6 C 0.3266(5) 0.4735(3) 0.6544(3) 0.0296(8) Uani 1 1 d . . .
H6A H 0.2853 0.5286 0.6778 0.036 Uiso 1 1 calc R . .
H6B H 0.3042 0.4276 0.6974 0.036 Uiso 1 1 calc R . .
O12 O 0.8501(5) 0.6890(3) 0.1616(2) 0.0446(8) Uani 1 1 d . . .
F9 F 0.1115(5) 0.8978(2) 0.7326(2) 0.0580(8) Uani 1 1 d . . .
C18 C -0.0356(6) 0.5218(4) -0.0850(3) 0.0492(12) Uani 1 1 d . . .
H18A H 0.0114 0.5165 -0.1429 0.074 Uiso 1 1 calc R . .
H18B H -0.0373 0.5827 -0.0678 0.074 Uiso 1 1 calc R . .
H18C H -0.1521 0.4989 -0.0883 0.074 Uiso 1 1 calc R . .
C11 C 0.3578(6) 0.4298(3) 0.1707(3) 0.0358(9) Uani 1 1 d . . .
H11A H 0.4285 0.4401 0.2262 0.043 Uiso 1 1 calc R . .
H11B H 0.2495 0.4029 0.1860 0.043 Uiso 1 1 calc R . .
N4 N 0.3741(5) 0.3680(3) 0.0182(3) 0.0369(8) Uani 1 1 d . . .
C13 C 0.0127(5) 0.4861(4) 0.0752(3) 0.0386(10) Uani 1 1 d . . .
H13A H 0.0009 0.4299 0.1050 0.046 Uiso 1 1 calc R . .
H13B H -0.1010 0.5139 0.0696 0.046 Uiso 1 1 calc R . .
C9 C 0.2102(6) 0.4806(4) 0.4047(3) 0.0401(10) Uani 1 1 d . . .
H9A H 0.2466 0.4212 0.3945 0.060 Uiso 1 1 calc R . .
H9B H 0.2480 0.5179 0.3578 0.060 Uiso 1 1 calc R . .
H9C H 0.0856 0.4827 0.4047 0.060 Uiso 1 1 calc R . .
C2 C 0.5304(6) 0.6415(3) 0.6450(3) 0.0355(9) Uani 1 1 d . . .
H2A H 0.4092 0.6510 0.6561 0.043 Uiso 1 1 calc R . .
H2B H 0.5970 0.6914 0.6690 0.043 Uiso 1 1 calc R . .
C5 C 0.2273(5) 0.4534(3) 0.5655(3) 0.0287(8) Uani 1 1 d . . .
H5A H 0.2448 0.3923 0.5495 0.034 Uiso 1 1 calc R . .
H5B H 0.1038 0.4626 0.5710 0.034 Uiso 1 1 calc R . .
C4 C 0.2370(6) 0.6049(3) 0.5076(3) 0.0326(9) Uani 1 1 d . . .
H4A H 0.1997 0.6120 0.5681 0.039 Uiso 1 1 calc R . .
H4B H 0.1398 0.6198 0.4653 0.039 Uiso 1 1 calc R . .
C12 C 0.1368(6) 0.5433(3) 0.1315(3) 0.0370(10) Uani 1 1 d . . .
H12A H 0.1229 0.6039 0.1119 0.044 Uiso 1 1 calc R . .
H12B H 0.1090 0.5401 0.1940 0.044 Uiso 1 1 calc R . .
C8 C 0.7001(6) 0.6880(3) 0.5219(3) 0.0387(10) Uani 1 1 d . . .
H8A H 0.6809 0.7487 0.5362 0.058 Uiso 1 1 calc R . .
H8B H 0.7141 0.6823 0.4585 0.058 Uiso 1 1 calc R . .
H8C H 0.8034 0.6675 0.5554 0.058 Uiso 1 1 calc R . .
C14 C 0.0654(7) 0.3767(3) -0.0415(3) 0.0424(11) Uani 1 1 d . . .
H14A H 0.0858 0.3701 -0.1048 0.051 Uiso 1 1 calc R . .
H14B H -0.0502 0.3545 -0.0326 0.051 Uiso 1 1 calc R . .
C3 C 0.3883(6) 0.6663(3) 0.4940(3) 0.0345(9) Uani 1 1 d . . .
H3A H 0.4090 0.6689 0.4305 0.041 Uiso 1 1 calc R . .
H3B H 0.3599 0.7251 0.5137 0.041 Uiso 1 1 calc R . .
C15 C 0.1973(7) 0.3242(3) 0.0143(3) 0.0461(11) Uani 1 1 d . . .
H15A H 0.2058 0.2658 -0.0114 0.055 Uiso 1 1 calc R . .
H15B H 0.1598 0.3180 0.0749 0.055 Uiso 1 1 calc R . .
C10 C 0.4517(7) 0.3682(3) 0.1120(3) 0.0445(11) Uani 1 1 d . . .
H10A H 0.5729 0.3856 0.1123 0.053 Uiso 1 1 calc R . .
H10B H 0.4476 0.3091 0.1365 0.053 Uiso 1 1 calc R . .
C19 C 0.1462(6) 0.8186(3) 0.7020(3) 0.0383(10) Uani 1 1 d . . .
C17 C 0.4377(7) 0.5849(4) 0.1654(3) 0.0467(12) Uani 1 1 d . . .
H17A H 0.4198 0.6391 0.1327 0.070 Uiso 1 1 calc R . .
H17B H 0.5564 0.5664 0.1627 0.070 Uiso 1 1 calc R . .
H17C H 0.4130 0.5937 0.2271 0.070 Uiso 1 1 calc R . .
C16 C 0.4890(9) 0.3172(5) -0.0403(4) 0.0643(17) Uani 1 1 d . . .
H16A H 0.5978 0.3475 -0.0433 0.096 Uiso 1 1 calc R . .
H16B H 0.4330 0.3119 -0.0998 0.096 Uiso 1 1 calc R . .
H16C H 0.5097 0.2596 -0.0152 0.096 Uiso 1 1 calc R . .
C7 C 0.6046(7) 0.3997(4) 0.6858(4) 0.0520(14) Uani 1 1 d . . .
H7A H 0.7274 0.4024 0.6787 0.078 Uiso 1 1 calc R . .
H7B H 0.5568 0.3481 0.6561 0.078 Uiso 1 1 calc R . .
H7C H 0.5849 0.3971 0.7488 0.078 Uiso 1 1 calc R . .
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'
F F 0.0171 0.0103 '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'
Mo Mo -1.6832 0.6857 '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
_geom_angle_publ_flag
O2 Mo1 O3 106.52(19) . . ?
O2 Mo1 O1 106.39(15) . . ?
O3 Mo1 O1 105.07(17) . . ?
O2 Mo1 N1 87.09(13) . . ?
O3 Mo1 N1 88.35(15) . . ?
O1 Mo1 N1 156.87(13) . . ?
O2 Mo1 N3 157.57(14) . . ?
O3 Mo1 N3 86.19(15) . . ?
O1 Mo1 N3 87.34(13) . . ?
N1 Mo1 N3 74.63(11) . . ?
O2 Mo1 N2 89.19(16) . . ?
O3 Mo1 N2 155.91(14) . . ?
O1 Mo1 N2 87.20(13) . . ?
N1 Mo1 N2 74.03(12) . . ?
N3 Mo1 N2 73.53(12) . . ?
O5 Mo2 O6 106.15(17) . . ?
O5 Mo2 O4 106.77(17) . . ?
O6 Mo2 O4 105.50(19) . . ?
O5 Mo2 N4 88.72(16) . . ?
O6 Mo2 N4 85.54(18) . . ?
O4 Mo2 N4 157.07(15) . . ?
O5 Mo2 N5 156.74(15) . . ?
O6 Mo2 N5 88.77(13) . . ?
O4 Mo2 N5 85.53(14) . . ?
N4 Mo2 N5 74.49(13) . . ?
O5 Mo2 N6 86.44(14) . . ?
O6 Mo2 N6 156.44(15) . . ?
O4 Mo2 N6 89.18(15) . . ?
N4 Mo2 N6 74.71(14) . . ?
N5 Mo2 N6 73.83(11) . . ?
O10 S2 O12 116.1(2) . . ?
O10 S2 O11 114.3(2) . . ?
O12 S2 O11 114.6(2) . . ?
O10 S2 C20 103.6(2) . . ?
O12 S2 C20 103.5(2) . . ?
O11 S2 C20 102.4(2) . . ?
O9 S1 O7 115.8(3) . . ?
O9 S1 O8 115.3(2) . . ?
O7 S1 O8 113.7(2) . . ?
O9 S1 C19 103.8(2) . . ?
O7 S1 C19 103.1(2) . . ?
O8 S1 C19 102.6(2) . . ?
C7 N1 C1 108.5(4) . . ?
C7 N1 C6 108.9(3) . . ?
C1 N1 C6 111.6(3) . . ?
C7 N1 Mo1 107.9(3) . . ?
C1 N1 Mo1 106.4(2) . . ?
C6 N1 Mo1 113.4(2) . . ?
C5 N3 C9 108.6(3) . . ?
C5 N3 C4 111.4(3) . . ?
C9 N3 C4 109.2(3) . . ?
C5 N3 Mo1 104.8(2) . . ?
C9 N3 Mo1 108.7(2) . . ?
C4 N3 Mo1 114.1(2) . . ?
C12 N5 C17 109.3(4) . . ?
C12 N5 C11 111.7(3) . . ?
C17 N5 C11 109.3(3) . . ?
C12 N5 Mo2 106.8(2) . . ?
C17 N5 Mo2 107.0(3) . . ?
C11 N5 Mo2 112.6(3) . . ?
C18 N6 C14 108.5(4) . . ?
C18 N6 C13 109.9(4) . . ?
C14 N6 C13 111.0(4) . . ?
C18 N6 Mo2 108.5(3) . . ?
C14 N6 Mo2 105.2(3) . . ?
C13 N6 Mo2 113.5(2) . . ?
F4 C20 F6 106.1(4) . . ?
F4 C20 F5 107.4(4) . . ?
F6 C20 F5 108.4(4) . . ?
F4 C20 S2 112.4(3) . . ?
F6 C20 S2 110.5(3) . . ?
F5 C20 S2 111.7(3) . . ?
C8 N2 C2 109.3(3) . . ?
C8 N2 C3 109.4(3) . . ?
C2 N2 C3 111.3(3) . . ?
C8 N2 Mo1 108.2(3) . . ?
C2 N2 Mo1 112.7(2) . . ?
C3 N2 Mo1 105.7(2) . . ?
N1 C1 C2 110.5(3) . . ?
N1 C6 C5 112.0(3) . . ?
C10 C11 N5 111.4(4) . . ?
C10 N4 C16 109.5(4) . . ?
C10 N4 C15 109.9(4) . . ?
C16 N4 C15 108.5(4) . . ?
C10 N4 Mo2 106.7(3) . . ?
C16 N4 Mo2 108.6(3) . . ?
C15 N4 Mo2 113.6(3) . . ?
N6 C13 C12 111.4(3) . . ?
N2 C2 C1 110.5(4) . . ?
N3 C5 C6 109.9(3) . . ?
N3 C4 C3 110.6(3) . . ?
N5 C12 C13 111.7(4) . . ?
N6 C14 C15 111.2(4) . . ?
N2 C3 C4 110.3(3) . . ?
C14 C15 N4 111.1(4) . . ?
N4 C10 C11 111.8(4) . . ?
F7 C19 F8 107.3(4) . . ?
F7 C19 F9 108.1(4) . . ?
F8 C19 F9 107.6(4) . . ?
F7 C19 S1 110.7(4) . . ?
F8 C19 S1 111.3(3) . . ?
F9 C19 S1 111.6(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mo1 O2 1.696(3) . ?
Mo1 O3 1.704(3) . ?
Mo1 O1 1.873(3) . ?
Mo1 N1 2.288(3) . ?
Mo1 N3 2.341(3) . ?
Mo1 N2 2.352(3) . ?
Mo2 O5 1.697(3) . ?
Mo2 O6 1.697(3) . ?
Mo2 O4 1.871(4) . ?
Mo2 N4 2.289(4) . ?
Mo2 N5 2.331(3) . ?
Mo2 N6 2.339(3) . ?
S2 O10 1.430(4) . ?
S2 O12 1.438(3) . ?
S2 O11 1.451(3) . ?
S2 C20 1.818(5) . ?
S1 O9 1.428(4) . ?
S1 O7 1.434(4) . ?
S1 O8 1.448(4) . ?
S1 C19 1.825(5) . ?
N1 C7 1.493(6) . ?
N1 C1 1.486(6) . ?
N1 C6 1.497(5) . ?
N3 C5 1.489(5) . ?
N3 C9 1.491(5) . ?
N3 C4 1.490(5) . ?
N5 C12 1.478(5) . ?
N5 C17 1.490(6) . ?
N5 C11 1.500(6) . ?
F8 C19 1.333(6) . ?
F6 C20 1.341(5) . ?
N6 C18 1.488(6) . ?
N6 C14 1.483(6) . ?
N6 C13 1.498(5) . ?
C20 F4 1.325(6) . ?
C20 F5 1.320(6) . ?
N2 C8 1.489(5) . ?
N2 C2 1.486(5) . ?
N2 C3 1.489(5) . ?
C1 C2 1.509(7) . ?
F7 C19 1.328(5) . ?
C6 C5 1.511(6) . ?
F9 C19 1.321(6) . ?
C11 C10 1.499(7) . ?
N4 C10 1.478(6) . ?
N4 C16 1.497(6) . ?
N4 C15 1.513(7) . ?
C13 C12 1.502(6) . ?
C4 C3 1.518(6) . ?
C14 C15 1.496(7) . ?
