#------------------------------------------------------------------------------
#$Date: 2016-03-25 12:51:43 +0100 (vie 25 de mar de 2016) $
#$Revision: 179867 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/63/7016321.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_7016321
loop_
_publ_author_name
'Dostál, Libor'
'Jambor, Roman'
'R°užička, Aleš'
'Jirásko, Robert'
'Holeček, Jaroslav'
'De Proft, Frank'
_publ_section_title
;
 OCO and NCO chelated derivatives of heavier group 15 elements. Study
 on possibility of cyclization reaction via intramolecular ether bond
 cleavage.
;
_journal_issue                   35
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8922
_journal_page_last               8934
_journal_paper_doi               10.1039/c1dt10234f
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C16 H25 Cl O2 Sb, C F3 O3 S'
_chemical_formula_sum            'C17 H25 Cl F3 O5 S Sb'
_chemical_formula_weight         555.63
_chemical_name_systematic
;
?
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 104.615(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3050(10)
_cell_length_b                   12.4460(12)
_cell_length_c                   19.4031(14)
_cell_measurement_reflns_used    17629
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     2174.4(4)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            17557
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.538
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.651
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.966
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0286P)²+1.6163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0786
_reflns_number_gt                3668
_reflns_number_total             4950
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10234f.txt
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7016321
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_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
Sb1 Sb 0.29742(2) 0.358721(18) 0.344472(11) 0.03058(8) Uani 1 1 d .
S1 S 0.30741(10) 0.35687(9) 0.16336(5) 0.0450(2) Uani 1 1 d .
Cl1 Cl 0.28437(10) 0.36552(8) 0.46610(5) 0.0488(2) Uani 1 1 d .
F1 F 0.0218(3) 0.3604(2) 0.14455(17) 0.0843(9) Uani 1 1 d .
O1 O 0.3662(2) 0.18078(18) 0.36523(13) 0.0375(5) Uani 1 1 d .
O2 O 0.3636(2) 0.53507(17) 0.35513(12) 0.0344(5) Uani 1 1 d .
C17 C 0.1229(5) 0.3588(4) 0.1066(2) 0.0621(12) Uani 1 1 d .
C1 C 0.5296(3) 0.3575(3) 0.36742(16) 0.0329(7) Uani 1 1 d .
C13 C 0.2644(4) 0.6297(3) 0.35292(19) 0.0391(8) Uani 1 1 d .
C6 C 0.6027(3) 0.4549(3) 0.37181(17) 0.0348(8) Uani 1 1 d .
F3 F 0.0960(3) 0.2728(3) 0.06592(19) 0.1276(15) Uani 1 1 d .
O3 O 0.3126(4) 0.4516(3) 0.20542(17) 0.0803(10) Uani 1 1 d .
C12 C 0.5164(3) 0.5570(3) 0.3564(2) 0.0411(8) Uani 1 1 d .
H12A H 0.5572 0.6098 0.3928 0.049 Uiso 1 1 d R
H12B H 0.5228 0.5855 0.3107 0.049 Uiso 1 1 d R
C14 C 0.2698(5) 0.6978(3) 0.2890(2) 0.0582(11) Uani 1 1 d .
H14A H 0.3639 0.7339 0.2976 0.070 Uiso 1 1 d R
H14B H 0.1914 0.7501 0.2806 0.070 Uiso 1 1 d R
H14C H 0.2575 0.6522 0.2480 0.070 Uiso 1 1 d R
C9 C 0.2702(5) 0.0205(3) 0.2973(2) 0.0550(10) Uani 1 1 d .
H9A H 0.2506 0.0653 0.2556 0.066 Uiso 1 1 d R
H9B H 0.1962 -0.0349 0.2911 0.066 Uiso 1 1 d R
H9C H 0.3666 -0.0116 0.3042 0.066 Uiso 1 1 d R
C8 C 0.2655(4) 0.0869(3) 0.36179(18) 0.0377(8) Uani 1 1 d .
O4 O 0.3998(3) 0.3567(3) 0.11490(16) 0.0686(9) Uani 1 1 d .
C4 C 0.8331(4) 0.3595(4) 0.4037(2) 0.0498(9) Uani 1 1 d .
H4 H 0.9364 0.3601 0.4159 0.060 Uiso 1 1 d R
O5 O 0.3093(4) 0.2615(3) 0.20468(18) 0.0830(11) Uani 1 1 d .
C5 C 0.7577(4) 0.4552(3) 0.39015(19) 0.0451(9) Uani 1 1 d .
H5 H 0.8092 0.5198 0.3932 0.054 Uiso 1 1 d R
C2 C 0.6049(4) 0.2617(3) 0.38107(18) 0.0375(8) Uani 1 1 d .
C10 C 0.1125(4) 0.1346(3) 0.3539(3) 0.0559(11) Uani 1 1 d .
H10A H 0.1121 0.1778 0.3948 0.067 Uiso 1 1 d R
H10B H 0.0415 0.0775 0.3500 0.067 Uiso 1 1 d R
H10C H 0.0868 0.1783 0.3118 0.067 Uiso 1 1 d R
C15 C 0.1099(4) 0.5818(3) 0.3436(3) 0.0573(11) Uani 1 1 d .
H15A H 0.0397 0.6384 0.3435 0.069 Uiso 1 1 d R
H15B H 0.1106 0.5334 0.3822 0.069 Uiso 1 1 d R
H15C H 0.0821 0.5434 0.2993 0.069 Uiso 1 1 d R
C3 C 0.7600(4) 0.2627(3) 0.3994(2) 0.0465(9) Uani 1 1 d .
H3 H 0.8129 0.1987 0.4088 0.056 Uiso 1 1 d R
C16 C 0.3135(5) 0.6894(4) 0.4223(2) 0.0563(11) Uani 1 1 d .
H16A H 0.4031 0.7281 0.4230 0.068 Uiso 1 1 d R
H16B H 0.3317 0.6392 0.4611 0.068 Uiso 1 1 d R
H16C H 0.2376 0.7391 0.4270 0.068 Uiso 1 1 d R
F2 F 0.1008(4) 0.4442(3) 0.06536(19) 0.1260(15) Uani 1 1 d .
C7 C 0.5220(4) 0.1579(3) 0.3773(3) 0.0537(11) Uani 1 1 d .
H7A H 0.5392 0.1141 0.3388 0.064 Uiso 1 1 d R
H7B H 0.5569 0.1186 0.4215 0.064 Uiso 1 1 d R
C11 C 0.3135(4) 0.0232(4) 0.4302(2) 0.0568(11) Uani 1 1 d .
H11A H 0.4024 -0.0161 0.4303 0.068 Uiso 1 1 d R
H11B H 0.2362 -0.0262 0.4333 0.068 Uiso 1 1 d R
H11C H 0.3324 0.0711 0.4703 0.068 Uiso 1 1 d 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'
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'
S S 0.1246 0.1234 '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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.078
0 1 -1 0.100
0 -1 -1 0.139
1 0 0 0.040
-1 0 0 0.057
0 0 -1 0.170
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 Sb1 O2 75.32(11)
C1 Sb1 O1 74.37(11)
O2 Sb1 O1 148.40(8)
C1 Sb1 Cl1 95.56(9)
O2 Sb1 Cl1 87.49(6)
O1 Sb1 Cl1 86.72(6)
O4 S1 O3 116.0(2)
O4 S1 O5 116.4(2)
O3 S1 O5 111.8(2)
O4 S1 C17 103.79(19)
O3 S1 C17 103.3(2)
O5 S1 C17 103.3(2)
C7 O1 C8 116.7(3)
C7 O1 Sb1 116.2(2)
C8 O1 Sb1 126.91(18)
C12 O2 C13 116.9(2)
C12 O2 Sb1 115.28(19)
C13 O2 Sb1 127.47(18)
F2 C17 F3 108.5(4)
F2 C17 F1 107.5(4)
F3 C17 F1 106.8(4)
F2 C17 S1 111.3(4)
F3 C17 S1 111.5(3)
F1 C17 S1 111.1(3)
C2 C1 C6 122.0(3)
C2 C1 Sb1 119.8(2)
C6 C1 Sb1 118.2(2)
O2 C13 C16 108.6(3)
O2 C13 C14 108.5(3)
C16 C13 C14 113.0(3)
O2 C13 C15 104.7(3)
C16 C13 C15 111.3(3)
C14 C13 C15 110.3(3)
C1 C6 C5 118.6(3)
C1 C6 C12 120.2(3)
C5 C6 C12 121.2(3)
O2 C12 C6 108.7(3)
O2 C12 H12A 110.1
C6 C12 H12A 109.8
O2 C12 H12B 109.9
C6 C12 H12B 110.0
H12A C12 H12B 108.3
C13 C14 H14A 109.7
C13 C14 H14B 109.7
H14A C14 H14B 109.5
C13 C14 H14C 109.0
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C8 C9 H9A 109.9
C8 C9 H9B 109.1
H9A C9 H9B 109.5
C8 C9 H9C 109.4
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O1 C8 C9 108.5(3)
O1 C8 C10 105.2(3)
C9 C8 C10 110.7(3)
O1 C8 C11 109.2(3)
C9 C8 C11 112.1(3)
C10 C8 C11 110.9(3)
C5 C4 C3 121.8(3)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 119.5(3)
C4 C5 H5 120.5
C6 C5 H5 120.1
C1 C2 C3 119.1(3)
C1 C2 C7 120.5(3)
C3 C2 C7 120.4(3)
C8 C10 H10A 109.6
C8 C10 H10B 109.2
H10A C10 H10B 109.5
C8 C10 H10C 109.6
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C13 C15 H15A 109.5
C13 C15 H15B 109.4
H15A C15 H15B 109.5
C13 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C4 C3 C2 119.1(3)
C4 C3 H3 120.6
C2 C3 H3 120.3
C13 C16 H16A 109.1
C13 C16 H16B 109.5
H16A C16 H16B 109.5
C13 C16 H16C 109.8
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O1 C7 C2 108.9(3)
O1 C7 H7A 109.9
C2 C7 H7A 109.9
O1 C7 H7B 110.0
C2 C7 H7B 109.8
H7A C7 H7B 108.3
C8 C11 H11A 109.4
C8 C11 H11B 109.3
H11A C11 H11B 109.5
C8 C11 H11C 109.7
H11A C11 H11C 109.5
H11B C11 H11C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Sb1 C1 2.093(3)
Sb1 O2 2.275(2)
Sb1 O1 2.312(2)
Sb1 Cl1 2.3950(9)
S1 O4 1.425(3)
S1 O3 1.428(3)
S1 O5 1.430(3)
S1 C17 1.791(4)
F1 C17 1.333(5)
O1 C7 1.438(4)
O1 C8 1.488(4)
O2 C12 1.442(4)
O2 C13 1.490(4)
C17 F2 1.314(6)
C17 F3 1.315(5)
C1 C2 1.374(5)
C1 C6 1.383(5)
C13 C16 1.504(5)
C13 C14 1.514(5)
C13 C15 1.524(5)
C6 C5 1.396(4)
C6 C12 1.492(5)
C12 H12A 0.9700
C12 H12B 0.9700
C14 H14A 0.9599
C14 H14B 0.9600
C14 H14C 0.9600
C9 C8 1.510(5)
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9599
C8 C10 1.514(5)
C8 C11 1.514(5)
C4 C5 1.374(5)
C4 C3 1.376(5)
C4 H4 0.9300
C5 H5 0.9301
C2 C3 1.396(5)
C2 C7 1.497(5)
C10 H10A 0.9599
C10 H10B 0.9600
C10 H10C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C3 H3 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9601
C7 H7A 0.9701
C7 H7B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9598
