#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:30:16 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179331 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/28/4322879.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_4322879
loop_
_publ_author_name
'Holger Glas'
'Eberhardt Herdtweck'
'Georg R. J. Artus'
'Werner R. Thiel'
_publ_contact_author
;
       Dr. Eberhardt Herdtweck
       Anorganisch-chemisches Institut der
       Technischen Universität München
       Lichtenbergstrasse 4
       D-85747 Garching bei München
;
_publ_contact_author_email       herdtweck@vogon.anorg.chemie.tu-muenchen.de
_publ_contact_author_fax         ' 089 289 13473'
_publ_contact_author_phone       '089 289 13143'
_publ_section_title
;
 Chlorination of a Pyrazole Ligand in Vanadium(V)alkoxo Complexes1
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3644
_journal_page_last               3646
_journal_paper_doi               10.1021/ic9715355
_journal_volume                  37
_journal_year                    1998
_chemical_formula_sum            'C16 H22 Cl2 N3 O4 V'
_chemical_formula_weight         442.22
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                107.23(1)
_cell_angle_beta                 99.70(1)
_cell_angle_gamma                103.57(1)
_cell_formula_units_Z            2
_cell_length_a                   8.406(1)
_cell_length_b                   9.695(1)
_cell_length_c                   13.756(2)
_cell_measurement_reflns_used    1918
_cell_measurement_temperature    223(1)
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.3
_cell_volume                     1006.1(2)
_computing_cell_refinement       STRUX-V
_computing_data_collection       STRUX-V
_computing_data_reduction        STRUX-V
_computing_molecular_graphics    'PLATON PLUTON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(1)
_diffrn_measurement_device       'IPDS Stoe'
_diffrn_measurement_method       oscillation
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11759
_diffrn_reflns_theta_max         24.26
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        unknown
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  1
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'orange colored'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.074
_refine_ls_goodness_of_fit_obs   1.090
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_restrained_S_obs      1.090
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_obs          0.0433
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0754P)²+0.0941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1241
_refine_ls_wR_factor_obs         0.1139
_reflns_number_observed          2394
_reflns_number_total             2885
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic9715355_2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.0941P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.0941P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4322879
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
V1 V 0.06570(7) 0.59169(6) 0.24316(4) 0.0358(2) Uani 1 d . .
Cl1 Cl 0.20084(11) 0.42692(10) 0.16384(7) 0.0521(3) Uani 1 d . .
Cl2 Cl -0.00019(10) 0.77935(9) 0.36964(7) 0.0440(2) Uani 1 d . .
O1 O 0.0384(3) 0.6600(3) 0.1533(2) 0.0449(6) Uani 1 d . .
O2 O -0.1272(3) 0.4560(2) 0.2188(2) 0.0400(5) Uani 1 d . .
O3 O 0.1990(3) 0.1864(3) 0.3285(2) 0.0497(6) Uani 1 d . .
O4 O -0.0753(3) 0.0988(3) 0.2403(2) 0.0487(6) Uani 1 d . .
N1 N 0.3240(3) 0.7531(3) 0.3156(2) 0.0376(6) Uani 1 d . .
N2 N 0.1868(3) 0.5461(3) 0.3896(2) 0.0356(6) Uani 1 d . .
N3 N 0.1419(3) 0.4516(3) 0.4425(2) 0.0341(6) Uani 1 d . .
C1 C 0.3926(5) 0.8502(4) 0.2712(3) 0.0490(9) Uani 1 d . .
H1 H 0.3275(5) 0.8519(4) 0.2100(3) 0.059 Uiso 1 calc R .
C2 C 0.5548(5) 0.9474(4) 0.3120(3) 0.0529(9) Uani 1 d . .
H2 H 0.5985(5) 1.0130(4) 0.2789(3) 0.064 Uiso 1 calc R .
C3 C 0.6520(4) 0.9459(4) 0.4032(3) 0.0506(9) Uani 1 d . .
H3 H 0.7629(4) 1.0092(4) 0.4318(3) 0.061 Uiso 1 calc R .
C4 C 0.5821(4) 0.8495(4) 0.4509(3) 0.0439(8) Uani 1 d . .
H4 H 0.6445(4) 0.8486(4) 0.5132(3) 0.053 Uiso 1 calc R .
C5 C 0.4191(4) 0.7539(4) 0.4060(3) 0.0363(7) Uani 1 d . .
C6 C 0.3370(4) 0.6436(3) 0.4480(2) 0.0347(7) Uani 1 d . .
C7 C 0.3891(4) 0.6118(4) 0.5385(2) 0.0373(7) Uani 1 d . .
H7 H 0.4884(4) 0.6635(4) 0.5918(2) 0.045 Uiso 1 calc R .
C8 C 0.2631(4) 0.4883(4) 0.5322(2) 0.0385(7) Uani 1 d . .
H8 H 0.2612(4) 0.4388(4) 0.5807(2) 0.046 Uiso 1 calc R .
C9 C 0.0034(4) 0.3146(3) 0.3907(3) 0.0363(7) Uani 1 d . .
H9A H -0.0889(4) 0.3355(3) 0.3508(3) 0.044 Uiso 1 calc R .
H9B H -0.0372(4) 0.2774(3) 0.4429(3) 0.044 Uiso 1 calc R .
C10 C 0.0578(4) 0.1952(3) 0.3177(2) 0.0378(8) Uani 1 d . .
C11 C -0.0414(6) -0.0240(5) 0.1648(3) 0.0711(13) Uani 1 d . .
H11A H -0.0175(6) -0.0959(5) 0.1970(3) 0.085 Uiso 1 calc R .
H11B H 0.0558(6) 0.0151(5) 0.1407(3) 0.085 Uiso 1 calc R .
C12 C -0.1935(8) -0.0982(7) 0.0757(4) 0.108(2) Uani 1 d . .
H12A H -0.1751(8) -0.1804(7) 0.0241(4) 0.162 Uiso 1 calc R .
H12B H -0.2157(8) -0.0260(7) 0.0445(4) 0.162 Uiso 1 calc R .
H12C H -0.2886(8) -0.1366(7) 0.1005(4) 0.162 Uiso 1 calc R .
C13 C -0.2908(4) 0.3973(4) 0.1394(3) 0.0503(9) Uani 1 d . .
C14 C -0.4009(5) 0.2777(5) 0.1688(3) 0.0610(11) Uani 1 d . .
H14A H -0.4177(5) 0.3230(5) 0.2369(3) 0.092 Uiso 1 calc R .
H14B H -0.3468(5) 0.2012(5) 0.1706(3) 0.092 Uiso 1 calc R .
H14C H -0.5084(5) 0.2324(5) 0.1176(3) 0.092 Uiso 1 calc R .
C15 C -0.2592(6) 0.3341(6) 0.0333(3) 0.086(2) Uani 1 d . .
H15A H -0.1887(6) 0.4141(6) 0.0179(3) 0.128 Uiso 1 calc R .
H15B H -0.3651(6) 0.2895(6) -0.0194(3) 0.128 Uiso 1 calc R .
H15C H -0.2035(6) 0.2583(6) 0.0336(3) 0.128 Uiso 1 calc R .
C16 C -0.3618(5) 0.5296(5) 0.1470(4) 0.0807(15) Uani 1 d . .
H16A H -0.3805(5) 0.5673(5) 0.2156(4) 0.121 Uiso 1 calc R .
H16B H -0.4670(5) 0.4964(5) 0.0944(4) 0.121 Uiso 1 calc R .
H16C H -0.2826(5) 0.6088(5) 0.1357(4) 0.121 Uiso 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'
Cl Cl 0.1484 0.1585 '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'
V V 0.3005 0.5294 '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
O1 V1 O2 104.13(11) . . ?
O1 V1 N1 91.29(11) . . ?
O2 V1 N1 164.24(10) . . ?
O1 V1 Cl1 96.49(9) . . ?
O2 V1 Cl1 96.46(8) . . ?
N1 V1 Cl1 84.80(7) . . ?
O1 V1 N2 162.29(11) . . ?
O2 V1 N2 93.57(10) . . ?
N1 V1 N2 71.01(9) . . ?
Cl1 V1 N2 81.59(7) . . ?
O1 V1 Cl2 95.53(9) . . ?
O2 V1 Cl2 93.57(8) . . ?
N1 V1 Cl2 81.55(7) . . ?
Cl1 V1 Cl2 161.98(4) . . ?
N2 V1 Cl2 82.87(7) . . ?
C13 O2 V1 136.2(2) . . ?
C10 O4 C11 115.8(3) . . ?
C1 N1 C5 117.9(3) . . ?
C1 N1 V1 121.6(2) . . ?
C5 N1 V1 120.4(2) . . ?
C6 N2 N3 105.8(2) . . ?
C6 N2 V1 116.3(2) . . ?
N3 N2 V1 137.6(2) . . ?
C8 N3 N2 110.7(3) . . ?
C8 N3 C9 128.1(3) . . ?
N2 N3 C9 119.6(2) . . ?
N1 C1 C2 123.0(3) . . ?
N1 C1 H1 118.5(2) . . ?
C2 C1 H1 118.5(2) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6(2) . . ?
C3 C2 H2 120.6(2) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6(2) . . ?
C2 C3 H3 120.6(2) . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1(2) . . ?
C5 C4 H4 120.1(2) . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 114.6(3) . . ?
C4 C5 C6 123.7(3) . . ?
N2 C6 C7 110.7(3) . . ?
N2 C6 C5 117.2(3) . . ?
C7 C6 C5 132.0(3) . . ?
C8 C7 C6 105.3(3) . . ?
C8 C7 H7 127.3(2) . . ?
C6 C7 H7 127.3(2) . . ?
N3 C8 C7 107.5(3) . . ?
N3 C8 H8 126.3(2) . . ?
C7 C8 H8 126.3(2) . . ?
N3 C9 C10 110.7(2) . . ?
N3 C9 H9A 109.5(2) . . ?
C10 C9 H9A 109.5(2) . . ?
N3 C9 H9B 109.5(2) . . ?
C10 C9 H9B 109.5(2) . . ?
H9A C9 H9B 108.1 . . ?
O3 C10 O4 124.9(3) . . ?
O3 C10 C9 125.2(3) . . ?
O4 C10 C9 110.0(3) . . ?
O4 C11 C12 107.4(4) . . ?
O4 C11 H11A 110.2(2) . . ?
C12 C11 H11A 110.2(3) . . ?
O4 C11 H11B 110.2(2) . . ?
C12 C11 H11B 110.2(4) . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5(3) . . ?
C11 C12 H12B 109.5(3) . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5(4) . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 C15 107.9(3) . . ?
O2 C13 C14 106.0(3) . . ?
C15 C13 C14 112.4(4) . . ?
O2 C13 C16 107.1(3) . . ?
C15 C13 C16 111.6(4) . . ?
C14 C13 C16 111.5(4) . . ?
C13 C14 H14A 109.5(2) . . ?
C13 C14 H14B 109.5(2) . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5(2) . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5(3) . . ?
C13 C15 H15B 109.5(2) . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5(3) . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5(3) . . ?
C13 C16 H16B 109.5(2) . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5(2) . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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
V1 O1 1.575(2) . ?
V1 O2 1.739(2) . ?
V1 N1 2.215(3) . ?
V1 Cl1 2.2955(10) . ?
V1 N2 2.310(3) . ?
V1 Cl2 2.3594(10) . ?
O2 C13 1.472(4) . ?
O3 C10 1.197(4) . ?
O4 C10 1.333(4) . ?
O4 C11 1.450(4) . ?
N1 C1 1.340(4) . ?
N1 C5 1.357(4) . ?
N2 C6 1.335(4) . ?
N2 N3 1.355(4) . ?
N3 C8 1.354(4) . ?
N3 C9 1.436(4) . ?
C1 C2 1.374(5) . ?
C1 H1 0.93 . ?
C2 C3 1.383(5) . ?
C2 H2 0.93 . ?
C3 C4 1.373(5) . ?
C3 H3 0.93 . ?
C4 C5 1.377(5) . ?
C4 H4 0.93 . ?
C5 C6 1.452(4) . ?
C6 C7 1.394(4) . ?
C7 C8 1.369(5) . ?
C7 H7 0.93 . ?
C8 H8 0.93 . ?
C9 C10 1.507(4) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C11 C12 1.474(6) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C13 C15 1.501(6) . ?
C13 C14 1.505(5) . ?
C13 C16 1.521(6) . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
