#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:08:28 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179502 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/99/4339991.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_4339991
loop_
_publ_author_name
'Richtera, Lukas'
'Jancik, Vojtech'
'Martínez-Otero, Diego'
'Pokluda, Ales'
'Zak, Zdirad'
'Taraba, Jan'
'Touzin, Jiri'
_publ_section_title
;
 Taming the Oxidative Power of SeO3 in 1,4-Dioxane, Isolation of Two New
 Isomers of Mixed-Valence Selenium Oxides, and Two Unprecedented Cyclic
 Esters of Selenic Acid.
;
_journal_issue                   13
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6569
_journal_page_last               6577
_journal_paper_doi               10.1021/ic500137z
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C4 H8 O5 Se'
_chemical_formula_sum            'C4 H8 O5 Se'
_chemical_formula_weight         215.06
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                118.799(5)
_cell_angle_beta                 93.758(4)
_cell_angle_gamma                105.026(4)
_cell_formula_units_Z            4
_cell_length_a                   7.3786(3)
_cell_length_b                   10.4307(6)
_cell_length_c                   10.6527(5)
_cell_measurement_reflns_used    9786
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.365
_cell_measurement_theta_min      3.266
_cell_volume                     676.11(7)
_computing_cell_refinement       '1.171.35.19 CrysAlis171'
_computing_data_collection       '1.169 CrysAlis169'
_computing_data_reduction        '1.171.35.19 CrysAlis171'
_computing_molecular_graphics    'Gretep and POV-Ray'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'KM4CCD/SAPPHIRE CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9786
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         3.266
_exptl_absorpt_coefficient_mu    5.516
_exptl_absorpt_correction_T_max  0.4319
_exptl_absorpt_correction_T_min  0.3828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs 2009/1, Sheldrick'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.113
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.237
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0218
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0150P)²+0.9032P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2573
_reflns_number_total             2719
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic500137z_si_002.cif
_cod_data_source_block           Compound5
_cod_depositor_comments
'Adding full bibliography for 4339987--4339996.cif.'
_cod_database_code               4339991
#BEGIN Tags that were not found in dictionaries:
_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. 
;
_shelx_estimated_absorpt_t_min   0.608
_shelx_estimated_absorpt_t_max   0.770
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Se1 Se 0.27946(4) -0.02067(3) 0.22769(3) 0.01503(8) Uani 1 1 d . .
Se2 Se 0.76453(4) 0.53336(3) 0.28312(3) 0.01699(8) Uani 1 1 d . .
O1 O 0.2235(3) -0.1771(2) 0.0714(2) 0.0260(4) Uani 1 1 d . .
O2 O 0.2719(3) -0.0301(3) 0.3725(2) 0.0266(5) Uani 1 1 d . .
O3 O 0.3163(3) 0.1395(2) 0.2334(2) 0.0232(4) Uani 1 1 d . .
O4 O 0.5876(2) 0.0114(2) 0.25799(18) 0.0140(4) Uani 1 1 d . .
O5 O 0.9364(2) -0.0453(2) 0.20320(19) 0.0167(4) Uani 1 1 d . .
O6 O 0.7615(3) 0.5456(3) 0.1393(2) 0.0241(4) Uani 1 1 d . .
O7 O 0.6833(3) 0.3700(2) 0.2707(2) 0.0240(4) Uani 1 1 d . .
O8 O 0.8427(3) 0.6865(2) 0.4427(2) 0.0218(4) Uani 1 1 d . .
O9 O 0.4637(2) 0.5616(2) 0.28399(18) 0.0158(4) Uani 1 1 d . .
O10 O 0.0698(2) 0.5139(2) 0.28203(18) 0.0160(4) Uani 1 1 d . .
C1 C 0.6714(4) 0.0250(3) 0.1425(3) 0.0154(5) Uani 1 1 d . .
H1A H 0.6370 0.1042 0.1294 0.018 Uiso 1 1 calc R U
H1B H 0.6203 -0.0754 0.0482 0.018 Uiso 1 1 calc R U
C2 C 0.8867(4) 0.0712(3) 0.1858(3) 0.0169(5) Uani 1 1 d . .
H2A H 0.9456 0.0825 0.1092 0.020 Uiso 1 1 calc R U
H2B H 0.9376 0.1724 0.2794 0.020 Uiso 1 1 calc R U
C3 C 0.8535(4) -0.0580(3) 0.3177(3) 0.0171(5) Uani 1 1 d . .
H3A H 0.9041 0.0431 0.4113 0.020 Uiso 1 1 calc R U
H3B H 0.8902 -0.1356 0.3323 0.020 Uiso 1 1 calc R U
C4 C 0.6378(4) -0.1063(3) 0.2763(3) 0.0170(5) Uani 1 1 d . .
H4A H 0.5863 -0.2081 0.1834 0.020 Uiso 1 1 calc R U
H4B H 0.5811 -0.1162 0.3542 0.020 Uiso 1 1 calc R U
C5 C 0.3170(4) 0.4430(3) 0.1524(3) 0.0177(5) Uani 1 1 d . .
H5A H 0.2816 0.3434 0.1498 0.021 Uiso 1 1 calc R U
H5B H 0.3674 0.4279 0.0641 0.021 Uiso 1 1 calc R U
C6 C 0.1424(4) 0.4920(3) 0.1519(3) 0.0167(5) Uani 1 1 d . .
H6A H 0.1770 0.5901 0.1515 0.020 Uiso 1 1 calc R U
H6B H 0.0416 0.4116 0.0624 0.020 Uiso 1 1 calc R U
C7 C 0.2171(4) 0.6311(3) 0.4140(3) 0.0189(6) Uani 1 1 d . .
H7A H 0.1668 0.6458 0.5021 0.023 Uiso 1 1 calc R U
H7B H 0.2540 0.7313 0.4175 0.023 Uiso 1 1 calc R U
C8 C 0.3900(4) 0.5799(3) 0.4128(3) 0.0190(6) Uani 1 1 d . .
H8A H 0.4908 0.6582 0.5031 0.023 Uiso 1 1 calc R U
H8B H 0.3534 0.4803 0.4102 0.023 Uiso 1 1 calc R U
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'
Se Se -0.0929 2.2259 '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_3
O3 Se1 O2 121.32(11) .
O3 Se1 O1 118.90(11) .
O2 Se1 O1 119.35(12) .
O3 Se1 O4 91.59(8) .
O2 Se1 O4 91.00(8) .
O1 Se1 O4 94.03(8) .
O3 Se1 O5 86.88(8) 1_455
O2 Se1 O5 88.11(8) 1_455
O1 Se1 O5 88.45(8) 1_455
O4 Se1 O5 177.50(6) 1_455
O7 Se2 O6 120.87(11) .
O7 Se2 O8 118.77(11) .
O6 Se2 O8 120.32(11) .
O7 Se2 O9 91.55(8) .
O6 Se2 O9 87.81(8) .
O8 Se2 O9 88.78(8) .
O7 Se2 O10 90.66(8) 1_655
O6 Se2 O10 90.88(8) 1_655
O8 Se2 O10 90.34(8) 1_655
O9 Se2 O10 177.78(7) 1_655
C4 O4 C1 109.70(18) .
C4 O4 Se1 114.16(14) .
C1 O4 Se1 113.28(13) .
C2 O5 C3 109.22(18) .
C5 O9 C8 109.36(19) .
C5 O9 Se2 114.60(14) .
C8 O9 Se2 115.20(13) .
C7 O10 C6 110.24(19) .
C7 O10 Se2 115.84(14) 1_455
C6 O10 Se2 116.44(13) 1_455
O4 C1 C2 108.84(19) .
O5 C2 C1 109.7(2) .
O5 C3 C4 110.00(19) .
O4 C4 C3 108.5(2) .
O9 C5 C6 109.3(2) .
O10 C6 C5 109.30(19) .
O10 C7 C8 109.1(2) .
O9 C8 C7 109.0(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 O3 1.5911(19) .
Se1 O2 1.5959(18) .
Se1 O1 1.5960(19) .
Se1 O4 2.1887(17) .
Se1 O5 2.4605(17) 1_455
Se2 O7 1.589(2) .
Se2 O6 1.5967(18) .
Se2 O8 1.5972(18) .
Se2 O9 2.3138(17) .
Se2 O10 2.3140(17) 1_655
O4 C4 1.463(3) .
O4 C1 1.463(3) .
O5 C2 1.444(3) .
O5 C3 1.446(3) .
O9 C5 1.450(3) .
O9 C8 1.454(3) .
O10 C7 1.452(3) .
O10 C6 1.455(3) .
O10 Se2 2.3140(17) 1_455
C1 C2 1.504(3) .
C3 C4 1.503(3) .
C5 C6 1.505(3) .
C7 C8 1.504(3) .
