#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/72/4117249.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_4117249
loop_
_publ_author_name
'Vanessa Nascimento'
'Eduardo E. Alberto'
'Daniel W. Tondo'
'Daniel Dambrowski'
'Michael R. Detty'
'Faruk Nome'
'Antonio L. Braga'
_publ_section_title
;
 GPx-Like Activity of Selenides and Selenoxides: Experimental Evidence for
 the Involvement of Hydroxy Perhydroxy Selenane as the Active Species
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              138
_journal_page_last               141
_journal_paper_doi               10.1021/ja209570y
_journal_volume                  134
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H14 O2 Se'
_chemical_formula_sum            'C14 H14 O2 Se'
_chemical_formula_weight         293.21
_chemical_name_common            (2-(benzylseleninyl)phenyl)methanol
_chemical_name_systematic
;
(2-(benzylseleninyl)phenyl)methanol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2010-10-25T12:52:26-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.76300(10)
_cell_length_b                   11.2526(2)
_cell_length_c                   22.7956(5)
_cell_measurement_reflns_used    5501
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.54
_cell_volume                     1221.76(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2/BIS/COSMO'
_computing_data_reduction        'Bruker SAINT/SADABS'
_computing_molecular_graphics    'Crystal Impact Diamond 3'
_computing_publication_material  'Bruker APEX2/XCIF'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'Bruker XS'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.023
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12087
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    3.059
_exptl_absorpt_correction_T_max  0.7103
_exptl_absorpt_correction_T_min  0.4813
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'XPREP (Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.35
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.02
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0304P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0497
_reflns_number_gt                2926
_reflns_number_total             3057
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja209570y_si_002.cif
_cod_data_source_block           p212121
_cod_database_code               4117249
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
Se1 Se 0.67125(4) 0.555064(15) 0.234180(8) 0.01892(5) Uani 1 1 d .
O10 O 0.8268(3) 0.42339(11) 0.24801(6) 0.0281(3) Uani 1 1 d .
O9 O 0.4584(3) 0.75646(12) 0.20050(7) 0.0286(3) Uani 1 1 d .
H1 H 0.3553 0.81 0.2145 0.043 Uiso 1 1 calc R
C11 C 0.8830(4) 0.65739(18) 0.28917(8) 0.0224(4) Uani 1 1 d .
H8A H 1.0773 0.6274 0.2934 0.027 Uiso 1 1 calc R
H8B H 0.8918 0.7395 0.2737 0.027 Uiso 1 1 calc R
C12 C 0.7392(4) 0.65682(17) 0.34758(8) 0.0214(4) Uani 1 1 d .
C17 C 0.8046(5) 0.57223(18) 0.38981(9) 0.0281(4) Uani 1 1 d .
H14 H 0.944 0.5141 0.3817 0.034 Uiso 1 1 calc R
C16 C 0.6695(5) 0.57142(19) 0.44354(8) 0.0341(5) Uani 1 1 d .
H13 H 0.7169 0.513 0.4719 0.041 Uiso 1 1 calc R
C15 C 0.4666(5) 0.6548(2) 0.45608(9) 0.0325(5) Uani 1 1 d .
H12 H 0.3742 0.654 0.493 0.039 Uiso 1 1 calc R
C14 C 0.3977(4) 0.7403(2) 0.41431(9) 0.0305(5) Uani 1 1 d .
H11 H 0.2584 0.7982 0.4228 0.037 Uiso 1 1 calc R
C13 C 0.5319(4) 0.74099(18) 0.36042(9) 0.0253(4) Uani 1 1 d .
H10 H 0.4829 0.7991 0.332 0.03 Uiso 1 1 calc R
C2 C 0.8695(4) 0.60055(17) 0.16294(8) 0.0205(4) Uani 1 1 d .
C3 C 1.0489(4) 0.51548(18) 0.13975(9) 0.0252(4) Uani 1 1 d .
H2 H 1.0663 0.4402 0.1583 0.03 Uiso 1 1 calc R
C4 C 1.2023(5) 0.5400(2) 0.08978(9) 0.0333(5) Uani 1 1 d .
H3 H 1.3254 0.482 0.0738 0.04 Uiso 1 1 calc R
C5 C 1.1749(6) 0.6499(2) 0.06315(9) 0.0374(5) Uani 1 1 d .
H4 H 1.2805 0.6675 0.0289 0.045 Uiso 1 1 calc R
C6 C 0.9945(5) 0.7343(2) 0.08621(8) 0.0309(5) Uani 1 1 d .
H5 H 0.9769 0.8091 0.0672 0.037 Uiso 1 1 calc R
C7 C 0.8381(5) 0.71184(17) 0.13668(8) 0.0227(4) Uani 1 1 d .
C8 C 0.6545(5) 0.80745(16) 0.16170(9) 0.0269(4) Uani 1 1 d .
H7A H 0.7711 0.8663 0.1829 0.032 Uiso 1 1 calc R
H7B H 0.5547 0.8491 0.1296 0.032 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
Se1 0.01995(8) 0.01310(8) 0.02369(9) -0.00133(7) 0.00248(8) -0.00202(7)
O10 0.0351(7) 0.0143(6) 0.0349(7) 0.0038(5) 0.0059(6) 0.0023(6)
O9 0.0255(7) 0.0171(7) 0.0433(8) 0.0003(6) 0.0049(7) 0.0040(6)
C11 0.0225(9) 0.0207(9) 0.0238(8) -0.0022(7) 0.0013(7) -0.0064(8)
C12 0.0221(8) 0.0186(9) 0.0234(9) -0.0012(7) -0.0009(7) -0.0050(7)
C17 0.0312(10) 0.0226(10) 0.0306(9) 0.0011(8) -0.0018(9) 0.0027(10)
C16 0.0446(12) 0.0316(11) 0.0261(9) 0.0061(9) -0.0044(10) -0.0001(12)
C15 0.0359(11) 0.0386(12) 0.0229(9) -0.0025(9) 0.0031(9) -0.0082(11)
C14 0.0282(11) 0.0333(12) 0.0301(10) -0.0061(9) 0.0022(8) 0.0006(9)
C13 0.0278(10) 0.0213(10) 0.0267(10) -0.0003(8) 0.0002(8) -0.0022(9)
C2 0.0202(9) 0.0209(8) 0.0204(8) -0.0015(7) -0.0017(7) -0.0036(7)
C3 0.0261(10) 0.0233(10) 0.0263(9) -0.0049(8) -0.0001(8) 0.0005(8)
C4 0.0320(11) 0.0389(12) 0.0289(10) -0.0124(9) 0.0056(9) 0.0026(11)
C5 0.0434(12) 0.0474(13) 0.0213(9) -0.0028(9) 0.0073(10) -0.0105(14)
C6 0.0418(12) 0.0305(11) 0.0204(9) 0.0046(8) -0.0046(10) -0.0079(11)
C7 0.0257(9) 0.0216(9) 0.0207(8) -0.0005(7) -0.0075(8) -0.0026(9)
C8 0.0313(9) 0.0172(8) 0.0323(10) 0.0047(7) -0.0032(10) 0.0004(9)
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O10 Se1 C2 100.01(8)
O10 Se1 C11 99.72(8)
C2 Se1 C11 97.37(8)
C12 C11 Se1 109.13(12)
C17 C12 C13 118.49(18)
C17 C12 C11 121.11(18)
C13 C12 C11 120.40(18)
C16 C17 C12 120.9(2)
C15 C16 C17 120.38(19)
C16 C15 C14 119.61(19)
C13 C14 C15 120.1(2)
C14 C13 C12 120.5(2)
C3 C2 C7 121.43(19)
C3 C2 Se1 115.78(14)
C7 C2 Se1 122.79(15)
C4 C3 C2 120.1(2)
C3 C4 C5 119.4(2)
C4 C5 C6 120.3(2)
C5 C6 C7 121.4(2)
C6 C7 C2 117.3(2)
C6 C7 C8 119.73(17)
C2 C7 C8 122.89(18)
O9 C8 C7 109.47(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 O10 1.6864(13)
Se1 C2 1.9469(19)
Se1 C11 1.9785(18)
O9 C8 1.408(2)
C11 C12 1.497(3)
C12 C17 1.389(3)
C12 C13 1.399(3)
C17 C16 1.384(3)
C16 C15 1.377(3)
C15 C14 1.393(3)
C14 C13 1.385(3)
C2 C3 1.388(3)
C2 C7 1.396(3)
C3 C4 1.381(3)
C4 C5 1.384(3)
C5 C6 1.384(3)
C6 C7 1.394(3)
C7 C8 1.499(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660586
