#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151626.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_7151626
loop_
_publ_author_name
'Tripathi, Santosh K.'
'Sharma, Sagar'
'Singh, Harkesh B.'
'Butcher, Ray J.'
_publ_section_title
;
 2-Phenoxyethanol derived diselenide and related compounds; synthesis
 of a seven-membered seleninate ester.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              581
_journal_page_last               587
_journal_paper_doi               10.1039/C0OB00038H
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C16 H18 O4 Se2'
_chemical_formula_sum            'C16 H18 O4 Se2'
_chemical_formula_weight         432.22
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.1240(13)
_cell_length_b                   18.1240(13)
_cell_length_c                   9.8424(8)
_cell_measurement_reflns_used    2568
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      32.5425
_cell_measurement_theta_min      4.6199
_cell_volume                     3233.0(4)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
;
_computing_molecular_graphics    WinGX
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0376
_diffrn_reflns_av_sigmaI/netI    0.1141
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7512
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.56
_diffrn_reflns_theta_min         4.71
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    4.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.157
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0323
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²+0.3218P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                1423
_reflns_number_total             2642
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            C0OB00038H.TXT
_cod_data_source_block           15
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7151626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Se Se 0.970380(18) 0.693576(17) 0.05585(3) 0.03244(13) Uani 1 1 d . . .
O1 O 0.94683(11) 0.54234(11) 0.1192(2) 0.0304(5) Uani 1 1 d . . .
O2 O 0.79476(12) 0.50692(13) 0.0737(2) 0.0374(6) Uani 1 1 d . . .
H2B H 0.7797 0.5001 0.1513 0.056 Uiso 1 1 calc R . .
C1 C 1.02640(16) 0.63707(15) 0.1861(3) 0.0243(6) Uani 1 1 d . . .
C2 C 1.08509(19) 0.66287(19) 0.2617(4) 0.0394(8) Uani 1 1 d . . .
H2A H 1.1005 0.7116 0.2524 0.047 Uiso 1 1 calc R . .
C3 C 1.12114(19) 0.6162(2) 0.3514(4) 0.0415(9) Uani 1 1 d . . .
H3A H 1.1608 0.6336 0.4020 0.050 Uiso 1 1 calc R . .
C4 C 1.09860(19) 0.5449(2) 0.3658(4) 0.0408(9) Uani 1 1 d . . .
H4A H 1.1232 0.5141 0.4262 0.049 Uiso 1 1 calc R . .
C5 C 1.03986(18) 0.51766(18) 0.2920(3) 0.0354(8) Uani 1 1 d . . .
H5A H 1.0244 0.4692 0.3037 0.042 Uiso 1 1 calc R . .
C6 C 1.00430(16) 0.56334(17) 0.2004(3) 0.0256(6) Uani 1 1 d . . .
C7 C 0.91880(18) 0.46963(16) 0.1388(4) 0.0333(8) Uani 1 1 d . . .
H7A H 0.9039 0.4631 0.2327 0.040 Uiso 1 1 calc R . .
H7B H 0.9568 0.4336 0.1183 0.040 Uiso 1 1 calc R . .
C8 C 0.85409(18) 0.45851(18) 0.0470(3) 0.0345(8) Uani 1 1 d . . .
H8A H 0.8699 0.4653 -0.0463 0.041 Uiso 1 1 calc R . .
H8B H 0.8369 0.4081 0.0562 0.041 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se 0.0370(2) 0.02248(18) 0.0378(2) 0.00009(15) -0.00752(15) -0.00265(14)
O1 0.0310(12) 0.0230(11) 0.0371(12) 0.0036(10) -0.0042(10) -0.0050(10)
O2 0.0346(13) 0.0450(14) 0.0325(14) 0.0083(11) 0.0038(11) 0.0009(11)
C1 0.0245(15) 0.0215(15) 0.0268(16) 0.0026(13) 0.0009(13) 0.0031(12)
C2 0.041(2) 0.0328(18) 0.044(2) -0.0057(17) -0.0037(17) -0.0026(16)
C3 0.038(2) 0.040(2) 0.047(2) -0.0085(18) -0.0175(17) 0.0005(17)
C4 0.039(2) 0.041(2) 0.042(2) 0.0018(17) -0.0112(17) 0.0099(17)
C5 0.0354(18) 0.0268(17) 0.044(2) 0.0048(15) -0.0005(17) 0.0055(14)
C6 0.0216(14) 0.0267(15) 0.0284(16) -0.0027(13) 0.0046(13) 0.0019(12)
C7 0.0332(18) 0.0213(16) 0.046(2) 0.0014(15) 0.0008(16) -0.0037(14)
C8 0.0355(18) 0.0290(17) 0.0389(19) -0.0034(15) 0.0064(15) -0.0053(14)
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
_geom_angle_publ_flag
C1 Se Se 103.03(9) . 6_664 ?
C6 O1 C7 116.7(2) . . ?
C8 O2 H2B 109.5 . . ?
C2 C1 C6 119.3(3) . . ?
C2 C1 Se 125.7(2) . . ?
C6 C1 Se 115.0(2) . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3A 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 119.2(3) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
O1 C6 C5 124.7(3) . . ?
O1 C6 C1 115.1(3) . . ?
C5 C6 C1 120.2(3) . . ?
O1 C7 C8 108.8(3) . . ?
O1 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
O1 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O2 C8 C7 113.6(3) . . ?
O2 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
O2 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
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
Se C1 1.930(3) . ?
Se Se 2.3099(6) 6_664 ?
O1 C6 1.367(4) . ?
O1 C7 1.425(3) . ?
O2 C8 1.413(4) . ?
O2 H2B 0.8200 . ?
C1 C2 1.379(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.387(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.362(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.494(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2B O2 0.82 1.93 2.7207(14) 162.7 8_454
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se Se C1 C2 2.5(3) 6_664 . . . ?
Se Se C1 C6 -176.4(2) 6_664 . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
Se C1 C2 C3 -179.5(3) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C7 O1 C6 C5 4.8(4) . . . . ?
C7 O1 C6 C1 -175.0(3) . . . . ?
C4 C5 C6 O1 178.3(3) . . . . ?
C4 C5 C6 C1 -2.0(5) . . . . ?
C2 C1 C6 O1 -178.5(3) . . . . ?
Se C1 C6 O1 0.5(3) . . . . ?
C2 C1 C6 C5 1.7(5) . . . . ?
Se C1 C6 C5 -179.3(2) . . . . ?
C6 O1 C7 C8 176.9(3) . . . . ?
O1 C7 C8 O2 -62.0(4) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 50994247
