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#$Date: 2021-07-07 11:45:47 +0300 (Wed, 07 Jul 2021) $
#$Revision: 267325 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/39/1563999.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.
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data_1563999
loop_
_publ_author_name
'Harringer, Sophia'
'Matzinger, Manuel'
'Gajic, Natalie'
'Hejl, Michaela'
'Jakupec, Michael A.'
'Kandioller, Wolfgang'
'Keppler, Bernhard K.'
_publ_section_title
;
 First insights into the novel class of organometallic compounds bearing a
 bidentate selenopyridone coordination motif: Synthesis, characterization,
 stability and biological investigations
;
_journal_name_full               'Inorganica Chimica Acta'
_journal_page_first              119919
_journal_paper_doi               10.1016/j.ica.2020.119919
_journal_volume                  513
_journal_year                    2020
_chemical_formula_moiety         'C13 H13 N O Se'
_chemical_formula_sum            'C13 H13 N O Se'
_chemical_formula_weight         278.20
_chemical_name_systematic
1-Benzyl-3-hydroxy-2-methylpyridine-4(1H)-selenone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_cell_angle_alpha                109.332(2)
_cell_angle_beta                 95.120(3)
_cell_angle_gamma                107.446(2)
_cell_formula_units_Z            2
_cell_length_a                   7.1172(4)
_cell_length_b                   8.2231(5)
_cell_length_c                   11.2069(6)
_cell_measurement_reflns_used    8544
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.041
_cell_measurement_theta_min      2.753
_cell_volume                     577.35(6)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       APEX3
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.753
_diffrn_source                   'Sealed xray tube'
_diffrn_source_type              'Incoatec IuS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.228
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1606 before and 0.0741 after correction. 
The Ratio of minimum to maximum transmission is 0.7926. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2099
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0247
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0265P)²+0.3271P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0632
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1983
_reflns_number_total             2099
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ICA-2020-513-1199192.cif
_cod_data_source_block           mo_rap012_p-1
_cod_database_code               1563999
_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_max   0.882
_shelx_estimated_absorpt_t_min   0.564
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.62016(3) -0.40568(3) -0.20485(2) 0.01852(10) Uani 1 1 d . . . . .
O1 O 0.7345(3) -0.0067(2) -0.17323(15) 0.0220(4) Uani 1 1 d . . . . .
H1 H 0.705314 -0.111230 -0.231517 0.033 Uiso 1 1 calc GR . . . .
N1 N 0.7917(3) 0.1198(2) 0.17095(17) 0.0145(4) Uani 1 1 d . . . . .
C1 C 0.7879(3) 0.1358(3) 0.0531(2) 0.0147(4) Uani 1 1 d . . . . .
C2 C 0.7363(3) -0.0228(3) -0.0563(2) 0.0151(4) Uani 1 1 d . . . . .
C3 C 0.6853(3) -0.2004(3) -0.0506(2) 0.0151(4) Uani 1 1 d . . . . .
C4 C 0.6873(3) -0.2064(3) 0.0725(2) 0.0181(5) Uani 1 1 d . . . . .
H4 H 0.651792 -0.321694 0.082046 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7399(3) -0.0481(3) 0.1794(2) 0.0172(5) Uani 1 1 d . . . . .
H5 H 0.740099 -0.055789 0.262181 0.021 Uiso 1 1 calc R . . . .
C16 C 0.8502(4) 0.2913(3) 0.2903(2) 0.0175(5) Uani 1 1 d . . . . .
H16A H 0.744362 0.346643 0.290068 0.021 Uiso 1 1 calc R . . . .
H16B H 0.976763 0.380770 0.287041 0.021 Uiso 1 1 calc R . . . .
C17 C 0.8413(3) 0.3229(3) 0.0459(2) 0.0185(5) Uani 1 1 d . . . . .
H17A H 0.762173 0.389311 0.095096 0.028 Uiso 1 1 calc GR . . . .
H17B H 0.811399 0.309606 -0.044650 0.028 Uiso 1 1 calc GR . . . .
H17C H 0.985111 0.391764 0.082430 0.028 Uiso 1 1 calc GR . . . .
C18 C 0.8798(3) 0.2609(3) 0.4146(2) 0.0167(5) Uani 1 1 d . . . . .
C19 C 1.0691(3) 0.2725(3) 0.4699(2) 0.0172(5) Uani 1 1 d . . . . .
H19 H 1.178303 0.297311 0.427849 0.021 Uiso 1 1 calc R . . . .
C20 C 1.0993(4) 0.2481(3) 0.5858(2) 0.0203(5) Uani 1 1 d . . . . .
H20 H 1.228764 0.256003 0.622563 0.024 Uiso 1 1 calc R . . . .
C21 C 0.9401(4) 0.2120(3) 0.6484(2) 0.0213(5) Uani 1 1 d . . . . .
H21 H 0.960708 0.194985 0.727695 0.026 Uiso 1 1 calc R . . . .
C22 C 0.7517(4) 0.2012(3) 0.5944(2) 0.0229(5) Uani 1 1 d . . . . .
H22 H 0.642747 0.176378 0.636747 0.027 Uiso 1 1 calc R . . . .
C23 C 0.7215(4) 0.2264(3) 0.4786(2) 0.0203(5) Uani 1 1 d . . . . .
H23 H 0.592272 0.220067 0.442671 0.024 Uiso 1 1 calc 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'
N N 0.0061 0.0033 '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
C1 N1 C16 118.69(17) . .
C5 N1 C1 120.61(19) . .
C5 N1 C16 120.68(18) . .
N1 C1 C2 118.32(19) . .
N1 C1 C17 119.66(19) . .
C2 C1 C17 122.0(2) . .
O1 C2 C1 118.31(19) . .
O1 C2 C3 119.19(19) . .
C1 C2 C3 122.5(2) . .
C2 C3 Se1 118.89(16) . .
C4 C3 Se1 125.14(17) . .
C4 C3 C2 116.0(2) . .
C5 C4 C3 120.6(2) . .
N1 C5 C4 121.9(2) . .
N1 C16 C18 114.18(17) . .
C19 C18 C16 120.0(2) . .
C19 C18 C23 118.9(2) . .
C23 C18 C16 121.1(2) . .
C20 C19 C18 120.5(2) . .
C19 C20 C21 120.2(2) . .
C22 C21 C20 119.7(2) . .
C21 C22 C23 120.2(2) . .
C22 C23 C18 120.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C3 1.873(2) .
O1 C2 1.360(3) .
N1 C1 1.369(3) .
N1 C5 1.356(3) .
N1 C16 1.500(3) .
C1 C2 1.383(3) .
C1 C17 1.502(3) .
C2 C3 1.419(3) .
C3 C4 1.397(3) .
C4 C5 1.366(3) .
C16 C18 1.503(3) .
C18 C19 1.394(3) .
C18 C23 1.397(3) .
C19 C20 1.385(3) .
C20 C21 1.394(3) .
C21 C22 1.386(4) .
C22 C23 1.388(3) .
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
Se1 C3 C4 C5 179.08(17) . . . .
O1 C2 C3 Se1 0.6(3) . . . .
O1 C2 C3 C4 -179.04(19) . . . .
N1 C1 C2 O1 -179.34(19) . . . .
N1 C1 C2 C3 0.7(3) . . . .
N1 C16 C18 C19 90.0(2) . . . .
N1 C16 C18 C23 -92.0(2) . . . .
C1 N1 C5 C4 1.7(3) . . . .
C1 N1 C16 C18 -171.20(19) . . . .
C1 C2 C3 Se1 -179.40(16) . . . .
C1 C2 C3 C4 0.9(3) . . . .
C2 C3 C4 C5 -1.3(3) . . . .
C3 C4 C5 N1 0.0(3) . . . .
C5 N1 C1 C2 -2.0(3) . . . .
C5 N1 C1 C17 178.57(19) . . . .
C5 N1 C16 C18 10.0(3) . . . .
C16 N1 C1 C2 179.22(19) . . . .
C16 N1 C1 C17 -0.2(3) . . . .
C16 N1 C5 C4 -179.5(2) . . . .
C16 C18 C19 C20 178.80(19) . . . .
C16 C18 C23 C22 -179.1(2) . . . .
C17 C1 C2 O1 0.1(3) . . . .
C17 C1 C2 C3 -179.9(2) . . . .
C18 C19 C20 C21 -0.1(3) . . . .
C19 C18 C23 C22 -1.0(3) . . . .
C19 C20 C21 C22 -0.2(3) . . . .
C20 C21 C22 C23 -0.1(3) . . . .
C21 C22 C23 C18 0.7(3) . . . .
C23 C18 C19 C20 0.7(3) . . . .
