#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:08:28 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179502 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/99/4339988.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_4339988
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         'O7 Se3, 2(C4 H8 O2)'
_chemical_formula_sum            'C8 H16 O11 Se3'
_chemical_formula_weight         525.09
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 111.016(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.3762(2)
_cell_length_b                   10.8301(1)
_cell_length_c                   17.5751(2)
_cell_measurement_reflns_used    22537
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.371
_cell_measurement_theta_min      3.025
_cell_volume                     3087.38(7)
_computing_cell_refinement       'Version 1.171.35.19 CrysAlis171'
_computing_data_collection       '1.166 CrysAlis166'
_computing_data_reduction        'Version 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 0.994
_diffrn_measured_fraction_theta_max 0.992
_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  0.0168
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            22537
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.025
_diffrn_source                   'Sealed tube'
_exptl_absorpt_coefficient_mu    7.201
_exptl_absorpt_correction_T_max  0.4314
_exptl_absorpt_correction_T_min  0.3886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2009/1, Sheldrick'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.259
_exptl_crystal_description       prism
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0233
_refine_ls_R_factor_gt           0.0179
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0146P)²+1.9638P] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0382
_refine_ls_wR_factor_ref         0.0394
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5577
_reflns_number_total             6264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic500137z_si_002.cif
_cod_data_source_block           Compound2
_cod_depositor_comments
'Adding full bibliography for 4339987--4339996.cif.'
_cod_database_code               4339988
#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   0.327
_shelx_estimated_absorpt_t_max   0.327
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Se1 Se 0.50639(2) 0.17257(2) 0.14259(2) 0.01281(5) Uani 1 1 d . .
Se2 Se 0.70506(2) 0.11252(2) 0.24978(2) 0.01176(5) Uani 1 1 d . .
Se3 Se 0.58825(2) 0.19833(2) 0.33401(2) 0.01178(5) Uani 1 1 d . .
Se4 Se 0.49193(2) 0.86524(2) 0.35368(2) 0.01299(5) Uani 1 1 d . .
Se5 Se 0.40917(2) 0.82987(2) 0.16083(2) 0.01130(5) Uani 1 1 d . .
Se6 Se 0.29337(2) 0.90829(2) 0.25441(2) 0.01115(5) Uani 1 1 d . .
O1 O 0.60329(10) 0.12873(17) 0.15458(9) 0.0288(4) Uani 1 1 d . .
O2 O 0.64996(9) 0.07574(12) 0.31590(8) 0.0130(3) Uani 1 1 d . .
O3 O 0.49885(9) 0.16336(13) 0.23719(8) 0.0157(3) Uani 1 1 d . .
O4 O 0.49127(11) 0.31097(14) 0.11084(10) 0.0299(4) Uani 1 1 d . .
O5 O 0.44561(10) 0.07042(14) 0.08826(9) 0.0231(4) Uani 1 1 d . .
O6 O 0.72870(9) -0.02308(13) 0.23216(9) 0.0177(3) Uani 1 1 d . .
O7 O 0.62809(9) 0.31708(12) 0.30798(9) 0.0180(3) Uani 1 1 d . .
O8 O 0.49957(9) 0.86014(14) 0.25963(8) 0.0179(3) Uani 1 1 d . .
O9 O 0.34495(9) 0.94246(12) 0.18443(8) 0.0150(3) Uani 1 1 d . .
O10 O 0.39027(9) 0.84168(13) 0.33679(9) 0.0178(3) Uani 1 1 d . .
O11 O 0.53898(10) 0.74991(15) 0.40503(10) 0.0310(4) Uani 1 1 d . .
O12 O 0.51963(11) 0.99882(14) 0.39105(9) 0.0279(4) Uani 1 1 d . .
O13 O 0.37514(9) 0.70150(13) 0.17990(9) 0.0179(3) Uani 1 1 d . .
O14 O 0.28727(9) 1.04398(13) 0.28585(8) 0.0169(3) Uani 1 1 d . .
O15 O 0.48711(9) 0.34132(13) 0.37107(9) 0.0186(3) Uani 1 1 d . .
O16 O 0.33656(9) 0.44928(13) 0.36334(9) 0.0166(3) Uani 1 1 d . .
O17 O 0.51853(9) 0.71265(13) 0.12147(9) 0.0182(3) Uani 1 1 d . .
O18 O 0.67148(9) 0.61674(13) 0.12762(9) 0.0196(3) Uani 1 1 d . .
O19 O 0.27929(9) 0.32164(12) 0.64791(8) 0.0154(3) Uani 1 1 d . .
O20 O 0.19862(9) 0.32120(13) 0.47780(8) 0.0171(3) Uani 1 1 d . .
O21 O 0.30144(9) 0.80529(13) 0.52550(8) 0.0169(3) Uani 1 1 d . .
O22 O 0.22325(9) 0.83592(12) 0.35609(8) 0.0148(3) Uani 1 1 d . .
C1 C 0.42208(15) 0.2687(2) 0.38075(15) 0.0246(5) Uani 1 1 d . .
H1A H 0.4460 0.1984 0.4176 0.029 Uiso 1 1 calc R U
H1B H 0.3866 0.2352 0.3272 0.029 Uiso 1 1 calc R U
C2 C 0.37138(15) 0.3463(2) 0.41538(14) 0.0234(5) Uani 1 1 d . .
H2A H 0.3266 0.2956 0.4216 0.028 Uiso 1 1 calc R U
H2B H 0.4064 0.3765 0.4700 0.028 Uiso 1 1 calc R U
C3 C 0.40028(13) 0.52086(19) 0.35036(14) 0.0200(5) Uani 1 1 d . .
H3A H 0.4356 0.5584 0.4025 0.024 Uiso 1 1 calc R U
H3B H 0.3750 0.5885 0.3115 0.024 Uiso 1 1 calc R U
C4 C 0.45221(14) 0.44233(19) 0.31733(13) 0.0188(5) Uani 1 1 d . .
H4A H 0.4179 0.4103 0.2630 0.023 Uiso 1 1 calc R U
H4B H 0.4969 0.4930 0.3110 0.023 Uiso 1 1 calc R U
C5 C 0.54800(14) 0.59699(19) 0.16009(14) 0.0212(5) Uani 1 1 d . .
H5A H 0.5007 0.5419 0.1542 0.025 Uiso 1 1 calc R U
H5B H 0.5786 0.6103 0.2190 0.025 Uiso 1 1 calc R U
C6 C 0.60346(14) 0.5374(2) 0.12243(15) 0.0257(5) Uani 1 1 d . .
H6A H 0.6248 0.4586 0.1508 0.031 Uiso 1 1 calc R U
H6B H 0.5716 0.5185 0.0645 0.031 Uiso 1 1 calc R U
C7 C 0.64319(14) 0.7360(2) 0.09260(14) 0.0225(5) Uani 1 1 d . .
H7A H 0.6132 0.7272 0.0332 0.027 Uiso 1 1 calc R U
H7B H 0.6911 0.7908 0.1010 0.027 Uiso 1 1 calc R U
C8 C 0.58744(14) 0.7925(2) 0.13100(15) 0.0218(5) Uani 1 1 d . .
H8A H 0.6185 0.8068 0.1897 0.026 Uiso 1 1 calc R U
H8B H 0.5673 0.8733 0.1052 0.026 Uiso 1 1 calc R U
C9 C 0.26051(14) 0.20903(19) 0.60292(13) 0.0181(5) Uani 1 1 d . .
H9A H 0.2509 0.1429 0.6374 0.022 Uiso 1 1 calc R U
H9B H 0.3079 0.1843 0.5876 0.022 Uiso 1 1 calc R U
C10 C 0.18510(13) 0.22403(18) 0.52723(12) 0.0158(4) Uani 1 1 d . .
H10A H 0.1734 0.1458 0.4961 0.019 Uiso 1 1 calc R U
H10B H 0.1369 0.2443 0.5424 0.019 Uiso 1 1 calc R U
C11 C 0.21676(14) 0.43438(18) 0.52353(13) 0.0180(5) Uani 1 1 d . .
H11A H 0.1695 0.4577 0.5393 0.022 Uiso 1 1 calc R U
H11B H 0.2258 0.5014 0.4893 0.022 Uiso 1 1 calc R U
C12 C 0.29227(13) 0.41874(18) 0.59835(12) 0.0162(4) Uani 1 1 d . .
H12A H 0.3400 0.3984 0.5825 0.019 Uiso 1 1 calc R U
H12B H 0.3045 0.4968 0.6297 0.019 Uiso 1 1 calc R U
C13 C 0.31664(13) 0.72101(18) 0.46939(12) 0.0145(4) Uani 1 1 d . .
H13A H 0.3286 0.6378 0.4941 0.017 Uiso 1 1 calc R U
H13B H 0.3651 0.7489 0.4569 0.017 Uiso 1 1 calc R U
C14 C 0.24201(14) 0.71586(18) 0.39231(13) 0.0177(5) Uani 1 1 d . .
H14A H 0.2524 0.6582 0.3534 0.021 Uiso 1 1 calc R U
H14B H 0.1943 0.6845 0.4047 0.021 Uiso 1 1 calc R U
C15 C 0.21032(14) 0.92234(19) 0.41211(12) 0.0177(5) Uani 1 1 d . .
H15A H 0.1612 0.8978 0.4245 0.021 Uiso 1 1 calc R U
H15B H 0.2002 1.0055 0.3871 0.021 Uiso 1 1 calc R U
C16 C 0.28453(15) 0.92591(19) 0.48934(13) 0.0208(5) Uani 1 1 d . .
H16A H 0.3328 0.9555 0.4773 0.025 Uiso 1 1 calc R U
H16B H 0.2746 0.9843 0.5282 0.025 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_1
_geom_angle_site_symmetry_3
O4 Se1 O5 117.07(8) . .
O4 Se1 O1 109.96(9) . .
O5 Se1 O1 107.29(8) . .
O4 Se1 O3 109.55(8) . .
O5 Se1 O3 106.03(7) . .
O1 Se1 O3 106.37(7) . .
O6 Se2 O2 99.01(7) . .
O6 Se2 O1 97.70(8) . .
O2 Se2 O1 92.59(6) . .
O6 Se2 O18 89.00(6) . 2_645
O2 Se2 O18 86.36(6) . 2_645
O1 Se2 O18 173.30(6) . 2_645
O6 Se2 O19 83.93(6) . 4_665
O2 Se2 O19 176.27(5) . 4_665
O1 Se2 O19 84.72(5) . 4_665
O18 Se2 O19 96.02(5) 2_645 4_665
O7 Se3 O2 101.26(7) . .
O7 Se3 O3 101.77(7) . .
O2 Se3 O3 92.43(6) . .
O7 Se3 O21 92.14(6) . 3_666
O2 Se3 O21 82.55(5) . 3_666
O3 Se3 O21 165.90(5) . 3_666
O7 Se3 O15 89.63(6) . .
O2 Se3 O15 169.08(5) . .
O3 Se3 O15 86.18(5) . .
O21 Se3 O15 96.24(5) 3_666 .
O7 Se3 O12 175.61(6) . 1_545
O2 Se3 O12 81.53(5) . 1_545
O3 Se3 O12 81.39(5) . 1_545
O21 Se3 O12 84.83(5) 3_666 1_545
O15 Se3 O12 87.55(5) . 1_545
O11 Se4 O12 117.62(9) . .
O11 Se4 O10 105.80(8) . .
O12 Se4 O10 110.48(8) . .
O11 Se4 O8 108.81(8) . .
O12 Se4 O8 108.21(7) . .
O10 Se4 O8 105.23(7) . .
O13 Se5 O9 103.61(7) . .
O13 Se5 O8 101.84(7) . .
O9 Se5 O8 92.87(6) . .
O13 Se5 O20 88.12(6) . 2
O9 Se5 O20 86.56(6) . 2
O8 Se5 O20 169.85(6) . 2
O13 Se5 O17 89.52(6) . .
O9 Se5 O17 166.83(5) . .
O8 Se5 O17 83.29(5) . .
O20 Se5 O17 95.00(5) 2 .
O13 Se5 O5 167.73(6) . 1_565
O9 Se5 O5 75.97(5) . 1_565
O8 Se5 O5 90.41(5) . 1_565
O20 Se5 O5 79.62(4) 2 1_565
O17 Se5 O5 91.42(4) . 1_565
O14 Se6 O9 99.16(7) . .
O14 Se6 O10 103.59(7) . .
O9 Se6 O10 94.32(6) . .
O14 Se6 O16 88.31(6) . 2
O9 Se6 O16 85.46(6) . 2
O10 Se6 O16 167.96(6) . 2
O14 Se6 O22 86.22(6) . .
O9 Se6 O22 174.31(5) . .
O10 Se6 O22 82.54(5) . .
O16 Se6 O22 96.62(5) 2 .
Se1 O1 Se2 133.35(9) . .
Se2 O2 Se3 116.05(7) . .
Se1 O3 Se3 122.54(8) . .
Se4 O8 Se5 124.27(8) . .
Se5 O9 Se6 121.33(7) . .
Se4 O10 Se6 130.42(8) . .
C4 O15 C1 109.37(16) . .
C4 O15 Se3 117.11(11) . .
C1 O15 Se3 109.62(11) . .
C2 O16 C3 110.43(16) . .
C5 O17 C8 109.29(16) . .
C5 O17 Se5 118.51(12) . .
C8 O17 Se5 109.63(11) . .
C6 O18 C7 111.25(16) . .
C9 O19 C12 110.17(15) . .
C10 O20 C11 109.71(14) . .
C13 O21 C16 109.46(15) . .
C14 O22 C15 110.75(15) . .
C14 O22 Se6 119.16(12) . .
C15 O22 Se6 119.96(11) . .
O15 C1 C2 110.13(18) . .
O16 C2 C1 110.69(17) . .
O16 C3 C4 111.14(17) . .
O15 C4 C3 110.46(17) . .
O17 C5 C6 110.24(18) . .
O18 C6 C5 111.05(17) . .
O18 C7 C8 110.58(17) . .
O17 C8 C7 110.39(18) . .
O19 C9 C10 110.58(16) . .
O20 C10 C9 109.54(17) . .
O20 C11 C12 109.99(17) . .
O19 C12 C11 109.71(16) . .
O21 C13 C14 109.32(16) . .
O22 C14 C13 110.61(16) . .
O22 C15 C16 110.04(17) . .
O21 C16 C15 110.48(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 O4 1.5880(15) .
Se1 O5 1.5900(14) .
Se1 O1 1.6882(16) .
Se1 O3 1.7170(13) .
Se2 O6 1.5851(14) .
Se2 O2 1.7955(13) .
Se2 O1 1.9584(16) .
Se2 O18 2.4355(15) 2_645
Se2 O19 2.6521(14) 4_665
Se3 O7 1.6028(14) .
Se3 O2 1.8051(13) .
Se3 O3 1.8857(14) .
Se3 O21 2.5255(14) 3_666
Se3 O15 2.5946(14) .
Se3 O12 2.8201(15) 1_545
Se4 O11 1.5856(15) .
Se4 O12 1.5904(15) .
Se4 O10 1.7021(14) .
Se4 O8 1.7059(14) .
Se5 O13 1.5928(14) .
Se5 O9 1.7988(13) .
Se5 O8 1.9063(15) .
Se5 O20 2.4859(14) 2
Se5 O17 2.5776(14) .
Se5 O5 3.0649(15) 1_565
Se6 O14 1.5868(13) .
Se6 O9 1.8011(13) .
Se6 O10 1.9243(14) .
Se6 O16 2.4952(15) 2
Se6 O22 2.6181(14) .
O15 C4 1.430(2) .
O15 C1 1.436(3) .
O16 C2 1.431(2) .
O16 C3 1.435(2) .
O17 C5 1.429(2) .
O17 C8 1.438(2) .
O18 C6 1.438(3) .
O18 C7 1.439(2) .
O19 C9 1.426(2) .
O19 C12 1.434(2) .
O20 C10 1.437(2) .
O20 C11 1.437(2) .
O21 C13 1.436(2) .
O21 C16 1.436(2) .
O22 C14 1.433(2) .
O22 C15 1.433(2) .
C1 C2 1.496(3) .
C3 C4 1.500(3) .
C5 C6 1.497(3) .
C7 C8 1.496(3) .
C9 C10 1.504(3) .
C11 C12 1.497(3) .
C13 C14 1.503(3) .
C15 C16 1.500(3) .
