#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006413.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006413
loop_
_publ_author_name
'Polamo, M.'
'Mutikainen, I.'
'Leskel\"a, M.'
_publ_section_title
;
A Tetrahydrofuran Ring-Opening Product:
trans-Tetrachloro{4-[2-(phenylamino)pyridinio]butoxido-O}(tetrahydrofuran-O)zirconium(IV)
;
_journal_issue 8
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 1036
_journal_page_last 1037
_journal_volume 53
_journal_year 1997
_chemical_formula_iupac '[Zr Cl4 (C15 H18 N2 O) (C4 H8 O)]'
_chemical_formula_structural '[Zr Cl4 (C4 H8 O) (C15 H18 N1 O1)'
_chemical_formula_sum 'C19 H26 Cl4 N2 O2 Zr'
_chemical_formula_weight 547.44
_chemical_melting_point ?
_chemical_name_systematic
;
trans-Tetrachloro-[4-(2-(phenylamino)pyridinium)butoxo-O]
(tetrahydrofuran-O)zirconium(IV)
;
_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'
_audit_creation_method SHELXL
_cell_angle_alpha 90.00
_cell_angle_beta 99.89(3)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 14.251(5)
_cell_length_b 11.548(5)
_cell_length_c 14.280(7)
_cell_measurement_reflns_used 25
_cell_measurement_temperature 193.0(10)
_cell_measurement_theta_max 20
_cell_measurement_theta_min 3
_cell_volume 2315.1(17)
_computing_cell_refinement 'Rigaku AFC7S software'
_computing_data_collection
'Rigaku AFC7S software (Molecular Structure Corporation, 1992a)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1992b)'
_computing_molecular_graphics SHELXTL/PC
_computing_publication_material SHELXL-93
_computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution 'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature 193.0(10)
_diffrn_measurement_device 'Rigaku AFC-7S diffractometer'
_diffrn_measurement_method \w-2\q
_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 0.0000
_diffrn_reflns_av_sigmaI/netI 0.0259
_diffrn_reflns_limit_h_max 16
_diffrn_reflns_limit_h_min -16
_diffrn_reflns_limit_k_max 0
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 0
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 3560
_diffrn_reflns_theta_max 25.0
_diffrn_reflns_theta_min 2.57
_diffrn_standards_decay_% none
_diffrn_standards_interval_count 200
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 0.954
_exptl_absorpt_correction_T_max 0.867
_exptl_absorpt_correction_T_min 0.755
_exptl_absorpt_correction_type 'psi-scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.571
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_description prismatic
_exptl_crystal_F_000 1112
_exptl_crystal_size_max 0.45
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.15
_refine_diff_density_max 0.61
_refine_diff_density_min -0.49
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_all 1.079
_refine_ls_goodness_of_fit_obs 1.162
_refine_ls_hydrogen_treatment
'H atoms riding with U(H) = 1.3 U~eq~ of parent atom'
_refine_ls_matrix_type full
_refine_ls_number_parameters 253
_refine_ls_number_reflns 3560
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.079
_refine_ls_restrained_S_obs 1.162
_refine_ls_R_factor_all 0.0609
_refine_ls_R_factor_obs 0.0435
_refine_ls_shift/esd_max 0.013
_refine_ls_shift/esd_mean 0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0475P)^2^+1.7287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all 0.1057
_refine_ls_wR_factor_obs 0.0994
_reflns_number_observed 2766
_reflns_number_total 3560
_reflns_observed_criterion >2sigma(I)
_[local]_cod_data_source_file mu1299.cif
_[local]_cod_data_source_block zrapthf
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_[local]_cod_chemical_formula_sum_orig 'C19 H26 Cl4 N2 O2 Zr1'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.
Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_database_code 2006413
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Zr1 0.0396(2) 0.0309(2) 0.0370(2) 0.0000(2) 0.00105(15) 0.0018(2)
Cl1 0.0473(7) 0.0430(6) 0.0498(7) -0.0059(5) 0.0087(5) 0.0031(5)
Cl2 0.0437(6) 0.0333(5) 0.0523(7) 0.0030(4) 0.0083(5) 0.0001(5)
Cl3 0.0467(7) 0.0357(6) 0.0465(6) -0.0013(5) 0.0051(5) 0.0053(5)
Cl4 0.0579(8) 0.0416(6) 0.0653(8) 0.0038(5) 0.0175(6) -0.0059(5)
O1 0.051(2) 0.0357(15) 0.0461(15) 0.0023(15) -0.0062(12) 0.0051(14)
C2 0.070(3) 0.046(3) 0.050(3) 0.006(2) -0.008(2) -0.005(2)
C3 0.045(3) 0.081(4) 0.051(3) -0.001(2) -0.002(2) -0.003(2)
C4 0.053(3) 0.073(4) 0.062(3) 0.011(3) -0.002(2) 0.018(3)
C5 0.068(4) 0.045(3) 0.064(3) 0.010(2) -0.009(3) 0.013(2)
O6 0.056(2) 0.0384(15) 0.0372(14) -0.0068(15) -0.0003(12) 0.0005(14)
C7 0.060(3) 0.041(2) 0.040(2) -0.008(2) -0.005(2) -0.002(2)
C8 0.048(3) 0.039(2) 0.060(3) -0.010(2) 0.003(2) 0.001(2)
C9 0.045(2) 0.037(2) 0.049(2) -0.001(2) 0.007(2) -0.001(2)
C10 0.040(2) 0.040(2) 0.048(3) -0.003(2) 0.007(2) 0.001(2)
N11 0.038(2) 0.035(2) 0.047(2) 0.001(2) 0.005(2) 0.000(2)
C12 0.039(2) 0.031(2) 0.047(2) 0.006(2) 0.006(2) 0.001(2)
C13 0.044(3) 0.035(2) 0.060(3) -0.002(2) 0.004(2) -0.001(2)
C14 0.058(3) 0.038(2) 0.063(3) -0.001(2) 0.016(2) 0.003(2)
C15 0.061(3) 0.045(3) 0.048(3) 0.003(2) 0.008(2) 0.006(2)
C16 0.049(2) 0.045(2) 0.044(2) 0.011(2) 0.003(2) 0.003(2)
N17 0.048(2) 0.030(2) 0.056(2) -0.003(2) -0.007(2) 0.004(2)
C18 0.036(2) 0.036(2) 0.049(2) -0.003(2) 0.001(2) 0.000(2)
C19 0.045(3) 0.038(2) 0.062(3) 0.001(2) 0.004(2) -0.001(2)
C20 0.061(3) 0.043(3) 0.063(3) -0.010(2) 0.011(3) -0.009(2)
C21 0.052(3) 0.072(4) 0.052(3) -0.019(3) -0.002(2) -0.003(2)
C22 0.046(3) 0.061(3) 0.071(3) 0.006(2) -0.004(3) 0.012(3)
C23 0.041(2) 0.045(3) 0.055(3) 0.002(2) 0.002(2) 0.002(2)
loop_
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Zr1 0.25243(2) 0.24733(3) 0.36527(2) 0.03647(14) Uani d . 1 Zr
Cl1 0.35443(8) 0.40199(9) 0.31638(8) 0.0466(3) Uani d . 1 Cl
Cl2 0.16540(7) 0.40190(9) 0.44123(8) 0.0431(3) Uani d . 1 Cl
Cl3 0.16276(8) 0.10127(9) 0.44306(7) 0.0433(3) Uani d . 1 Cl
Cl4 0.35480(9) 0.09502(10) 0.31699(9) 0.0541(3) Uani d . 1 Cl
O1 0.3573(2) 0.2430(2) 0.5052(2) 0.0461(7) Uani d . 1 O
C2 0.4038(4) 0.3418(4) 0.5586(3) 0.0572(13) Uani d . 1 C
H2A 0.3568(4) 0.3879(4) 0.5864(3) 0.074 Uiso calc R 1 H
H2B 0.4341(4) 0.3925(4) 0.5165(3) 0.074 Uiso calc R 1 H
C3 0.4781(3) 0.2913(5) 0.6363(3) 0.0603(13) Uani d . 1 C
H3A 0.5390(3) 0.3340(5) 0.6413(3) 0.078 Uiso calc R 1 H
H3B 0.4563(3) 0.2945(5) 0.6984(3) 0.078 Uiso calc R 1 H
C4 0.4897(3) 0.1678(5) 0.6065(4) 0.0639(14) Uani d . 1 C
H4A 0.5365(3) 0.1618(5) 0.5630(4) 0.083 Uiso calc R 1 H
H4B 0.5100(3) 0.1173(5) 0.6623(4) 0.083 Uiso calc R 1 H
C5 0.3913(4) 0.1372(4) 0.5568(4) 0.0614(14) Uani d . 1 C
H5A 0.3932(4) 0.0717(4) 0.5124(4) 0.080 Uiso calc R 1 H
H5B 0.3499(4) 0.1160(4) 0.6032(4) 0.080 Uiso calc R 1 H
O6 0.1648(2) 0.2481(2) 0.2492(2) 0.0449(7) Uani d . 1 O
C7 0.1047(3) 0.2670(4) 0.1616(3) 0.0486(11) Uani d . 1 C
H7A 0.0619(3) 0.1997(4) 0.1456(3) 0.063 Uiso calc R 1 H
H7B 0.1432(3) 0.2764(4) 0.1106(3) 0.063 Uiso calc R 1 H
C8 0.0463(3) 0.3755(4) 0.1691(3) 0.0496(11) Uani d . 1 C
H8A 0.0149(3) 0.3687(4) 0.2255(3) 0.065 Uiso calc R 1 H
H8B -0.0043(3) 0.3805(4) 0.1123(3) 0.065 Uiso calc R 1 H
C9 0.1047(3) 0.4874(3) 0.1770(3) 0.0435(10) Uani d . 1 C
H9A 0.1687(3) 0.4727(3) 0.2147(3) 0.057 Uiso calc R 1 H
H9B 0.1130(3) 0.5130(3) 0.1128(3) 0.057 Uiso calc R 1 H
C10 0.0557(3) 0.5823(3) 0.2242(3) 0.0427(10) Uani d . 1 C
H10A -0.0121(3) 0.5867(3) 0.1937(3) 0.055 Uiso calc R 1 H
H10B 0.0579(3) 0.5627(3) 0.2921(3) 0.055 Uiso calc R 1 H
N11 0.1014(2) 0.6962(3) 0.2169(2) 0.0402(8) Uani d . 1 N
C12 0.1730(3) 0.7363(3) 0.2845(3) 0.0392(9) Uani d . 1 C
C13 0.2128(3) 0.8445(3) 0.2692(3) 0.0469(11) Uani d . 1 C
H13A 0.2634(3) 0.8742(3) 0.3150(3) 0.061 Uiso calc R 1 H
C14 0.1799(3) 0.9073(4) 0.1899(3) 0.0527(12) Uani d . 1 C
H14A 0.2071(3) 0.9808(4) 0.1812(3) 0.068 Uiso calc R 1 H
C15 0.1063(3) 0.8649(4) 0.1208(3) 0.0514(11) Uani d . 1 C
H15A 0.0833(3) 0.9082(4) 0.0650(3) 0.067 Uiso calc R 1 H
C16 0.0688(3) 0.7594(4) 0.1362(3) 0.0467(10) Uani d . 1 C
H16A 0.0189(3) 0.7287(4) 0.0901(3) 0.061 Uiso calc R 1 H
N17 0.2033(2) 0.6710(3) 0.3626(2) 0.0465(9) Uani d . 1 N
H17A 0.1860(2) 0.5977(3) 0.3603(2) 0.060 Uiso calc R 1 H
C18 0.2611(3) 0.7110(3) 0.4487(3) 0.0411(10) Uani d . 1 C
C19 0.2434(3) 0.8141(4) 0.4891(3) 0.0493(11) Uani d . 1 C
H19A 0.1932(3) 0.8625(4) 0.4591(3) 0.064 Uiso calc R 1 H
C20 0.2986(3) 0.8474(4) 0.5737(3) 0.0558(12) Uani d . 1 C
H20A 0.2870(3) 0.9197(4) 0.6015(3) 0.073 Uiso calc R 1 H
C21 0.3701(3) 0.7772(4) 0.6180(3) 0.0602(13) Uani d . 1 C
H21A 0.4087(3) 0.8010(4) 0.6758(3) 0.078 Uiso calc R 1 H
C22 0.3856(3) 0.6718(4) 0.5781(4) 0.0609(13) Uani d . 1 C
H22A 0.4336(3) 0.6217(4) 0.6100(4) 0.079 Uiso calc R 1 H
C23 0.3325(3) 0.6378(4) 0.4926(3) 0.0481(11) Uani d . 1 C
H23A 0.3445(3) 0.5660(4) 0.4644(3) 0.063 Uiso calc R 1 H
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -2.9673 0.5597 '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_publ_flag
O6 Zr1 O1 178.98(11) y
O6 Zr1 Cl4 95.25(9) y
O1 Zr1 Cl4 84.21(8) y
O6 Zr1 Cl1 94.60(9) y
O1 Zr1 Cl1 86.28(8) y
Cl4 Zr1 Cl1 91.81(4) y
O6 Zr1 Cl3 94.70(9) y
O1 Zr1 Cl3 84.45(8) y
Cl4 Zr1 Cl3 90.87(4) y
Cl1 Zr1 Cl3 170.04(4) y
O6 Zr1 Cl2 94.25(9) y
O1 Zr1 Cl2 86.29(8) y
Cl4 Zr1 Cl2 170.48(4) y
Cl1 Zr1 Cl2 88.09(4) y
Cl3 Zr1 Cl2 87.68(4) y
C5 O1 C2 107.8(3) n
C5 O1 Zr1 124.7(3) n
C2 O1 Zr1 127.5(2) n
O1 C2 C3 106.2(4) n
C4 C3 C2 104.8(4) n
C5 C4 C3 102.6(4) n
O1 C5 C4 104.1(4) n
C7 O6 Zr1 170.9(3) n
O6 C7 C8 108.9(3) n
C7 C8 C9 113.8(4) n
C10 C9 C8 110.8(3) n
N11 C10 C9 111.6(3) n
C12 N11 C16 121.2(4) n
C12 N11 C10 122.6(3) n
C16 N11 C10 116.2(3) n
N17 C12 N11 119.3(4) n
N17 C12 C13 122.9(4) n
N11 C12 C13 117.8(4) n
C14 C13 C12 120.9(4) n
C13 C14 C15 120.7(4) n
C16 C15 C14 117.8(4) n
C15 C16 N11 121.5(4) n
C12 N17 C18 125.5(3) n
C19 C18 C23 121.0(4) n
C19 C18 N17 121.5(4) n
C23 C18 N17 117.3(4) n
C18 C19 C20 119.7(4) n
C21 C20 C19 120.4(4) n
C20 C21 C22 119.5(4) n
C21 C22 C23 121.0(4) n
C22 C23 C18 118.4(4) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Zr1 O6 1.896(3) y
Zr1 O1 2.281(3) y
Zr1 Cl4 2.4581(12) y
Zr1 Cl1 2.4777(12) y
Zr1 Cl3 2.4899(12) y
Zr1 Cl2 2.5226(11) y
O1 C5 1.466(5) n
O1 C2 1.466(5) n
C2 C3 1.513(6) n
C3 C4 1.505(7) n
C4 C5 1.500(6) n
O6 C7 1.407(5) n
C7 C8 1.518(6) n
C8 C9 1.531(5) n
C9 C10 1.518(5) n
C10 N11 1.480(5) n
N11 C12 1.359(5) n
N11 C16 1.375(5) n
C12 N17 1.354(5) n
C12 C13 1.405(5) n
C13 C14 1.359(6) n
C14 C15 1.398(6) n
C15 C16 1.364(6) n
N17 C18 1.435(5) n
C18 C19 1.365(6) n
C18 C23 1.387(6) n
C19 C20 1.378(6) n
C20 C21 1.369(6) n
C21 C22 1.378(7) n
C22 C23 1.379(6) n