#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151099.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_7151099
loop_
_publ_author_name
'Aumann, Kylee M.'
'Scammells, Peter J.'
'White, Jonathan M.'
'Schiesser, Carl H.'
_publ_section_title
;
 On the stability of 2-aminoselenophene-3-carboxylates: potential
 dual-acting selenium-containing allosteric enhancers of A1 adenosine
 receptor binding.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1276
_journal_page_last               1281
_journal_paper_doi               10.1039/B700812K
_journal_volume                  5
_journal_year                    2007
_chemical_formula_sum            'C18 H18 N2 O5 Se'
_chemical_formula_weight         421.30
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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-97
_cell_angle_alpha                93.933(2)
_cell_angle_beta                 101.874(2)
_cell_angle_gamma                117.258(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6394(10)
_cell_length_b                   10.0481(11)
_cell_length_c                   10.1555(11)
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.32
_cell_volume                     840.58(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5132
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    2.267
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.943
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0475P)²+0.4717P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                3311
_reflns_number_total             3646
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B700812K.txt
_cod_data_source_block           jmwka2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        840.57(16)
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7151099
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8788(3) 0.7024(3) 0.4693(2) 0.0220(4) Uani 1 1 d . . .
C2 C 0.9623(3) 0.8177(3) 0.4047(2) 0.0208(4) Uani 1 1 d . . .
C3 C 0.8583(3) 0.8585(3) 0.3111(2) 0.0219(4) Uani 1 1 d . . .
C8 C 0.7001(3) 0.7750(3) 0.3050(2) 0.0235(5) Uani 1 1 d . . .
C7 C 0.5643(3) 0.7913(3) 0.2187(3) 0.0270(5) Uani 1 1 d . . .
H7A H 0.5307 0.8462 0.2757 0.032 Uiso 1 1 calc R . .
H7B H 0.4723 0.6911 0.1792 0.032 Uiso 1 1 calc R . .
C6 C 0.6172(4) 0.8758(4) 0.1059(3) 0.0389(6) Uani 1 1 d . . .
H6A H 0.6223 0.8090 0.0356 0.047 Uiso 1 1 calc R . .
H6B H 0.5381 0.9056 0.0645 0.047 Uiso 1 1 calc R . .
C5 C 0.7792(3) 1.0143(3) 0.1597(3) 0.0394(7) Uani 1 1 d . . .
H5A H 0.7715 1.0825 0.2266 0.047 Uiso 1 1 calc R . .
H5B H 0.8083 1.0667 0.0849 0.047 Uiso 1 1 calc R . .
C4 C 0.9136(3) 0.9804(3) 0.2262(2) 0.0256(5) Uani 1 1 d . . .
H4B H 0.9514 0.9481 0.1553 0.031 Uiso 1 1 calc R . .
H4A H 1.0040 1.0729 0.2840 0.031 Uiso 1 1 calc R . .
C9 C 1.1375(3) 0.8835(3) 0.4324(2) 0.0230(5) Uani 1 1 d . . .
C10 C 1.3765(3) 1.0559(3) 0.3797(3) 0.0283(5) Uani 1 1 d . . .
H10A H 1.4085 0.9775 0.3753 0.034 Uiso 1 1 calc R . .
H10B H 1.4324 1.1222 0.4689 0.034 Uiso 1 1 calc R . .
C11 C 1.4174(4) 1.1454(5) 0.2688(4) 0.0528(9) Uani 1 1 d . . .
H11A H 1.3602 1.0788 0.1812 0.079 Uiso 1 1 calc R . .
H11B H 1.5319 1.1916 0.2788 0.079 Uiso 1 1 calc R . .
H11C H 1.3864 1.2233 0.2751 0.079 Uiso 1 1 calc R . .
C12 C 0.8697(3) 0.5329(3) 0.6301(2) 0.0246(5) Uani 1 1 d . . .
C13 C 0.9701(3) 0.4915(3) 0.7344(2) 0.0225(4) Uani 1 1 d . . .
C14 C 0.8853(3) 0.3755(3) 0.7998(3) 0.0262(5) Uani 1 1 d . . .
H14 H 0.7728 0.3274 0.7762 0.031 Uiso 1 1 calc R . .
C15 C 0.9670(3) 0.3311(3) 0.8994(3) 0.0282(5) Uani 1 1 d . . .
H15 H 0.9108 0.2534 0.9436 0.034 Uiso 1 1 calc R . .
C16 C 1.1329(3) 0.4039(3) 0.9321(2) 0.0244(5) Uani 1 1 d . . .
C17 C 1.2212(3) 0.5168(3) 0.8677(3) 0.0262(5) Uani 1 1 d . . .
H17 H 1.3336 0.5622 0.8902 0.031 Uiso 1 1 calc R . .
C18 C 1.1376(3) 0.5610(3) 0.7682(3) 0.0263(5) Uani 1 1 d . . .
H18 H 1.1946 0.6380 0.7237 0.032 Uiso 1 1 calc R . .
N1 N 0.9509(3) 0.6440(2) 0.5636(2) 0.0234(4) Uani 1 1 d . . .
N2 N 1.2193(3) 0.3583(3) 1.0408(2) 0.0305(5) Uani 1 1 d . . .
O2 O 1.2195(2) 0.8467(2) 0.51495(18) 0.0287(4) Uani 1 1 d . . .
O3 O 1.2029(2) 0.98768(19) 0.35818(17) 0.0260(4) Uani 1 1 d . . .
O1 O 0.7230(2) 0.4697(2) 0.6067(2) 0.0365(4) Uani 1 1 d . . .
O4 O 1.1389(3) 0.2569(3) 1.0956(2) 0.0505(6) Uani 1 1 d . . .
O5 O 1.3665(2) 0.4235(2) 1.0706(2) 0.0407(5) Uani 1 1 d . . .
Se1 Se 0.65726(3) 0.62951(3) 0.41824(2) 0.02477(10) Uani 1 1 d . . .
H1 H 1.049(4) 0.688(4) 0.576(3) 0.037(9) Uiso 1 1 d . . .
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
_geom_angle_publ_flag
C2 C1 N1 124.1(2) . . ?
C2 C1 Se1 113.62(16) . . ?
N1 C1 Se1 122.24(17) . . ?
C1 C2 C3 113.2(2) . . ?
C1 C2 C9 119.6(2) . . ?
C3 C2 C9 127.1(2) . . ?
C8 C3 C2 113.5(2) . . ?
C8 C3 C4 120.7(2) . . ?
C2 C3 C4 125.8(2) . . ?
C3 C8 C7 125.9(2) . . ?
C3 C8 Se1 113.87(17) . . ?
C7 C8 Se1 120.28(18) . . ?
C8 C7 C6 110.5(2) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C5 C6 C7 111.0(2) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C5 C4 113.9(2) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C3 C4 C5 112.4(2) . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
H4B C4 H4A 107.9 . . ?
O2 C9 O3 121.9(2) . . ?
O2 C9 C2 124.2(2) . . ?
O3 C9 C2 113.91(19) . . ?
O3 C10 C11 106.9(2) . . ?
O3 C10 H10A 110.4 . . ?
C11 C10 H10A 110.4 . . ?
O3 C10 H10B 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 N1 122.0(2) . . ?
O1 C12 C13 121.5(2) . . ?
N1 C12 C13 116.5(2) . . ?
C18 C13 C14 119.6(2) . . ?
C18 C13 C12 124.5(2) . . ?
C14 C13 C12 115.9(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C15 C16 C17 122.9(2) . . ?
C15 C16 N2 118.2(2) . . ?
C17 C16 N2 118.8(2) . . ?
C16 C17 C18 117.9(2) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C13 C18 C17 120.6(2) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C12 N1 C1 124.4(2) . . ?
C12 N1 H1 125(2) . . ?
C1 N1 H1 111(2) . . ?
O5 N2 O4 123.8(2) . . ?
O5 N2 C16 118.3(2) . . ?
O4 N2 C16 117.9(2) . . ?
C9 O3 C10 116.55(18) . . ?
C1 Se1 C8 85.76(10) . . ?
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
C1 C2 1.374(3) . ?
C1 N1 1.386(3) . ?
C1 Se1 1.851(2) . ?
C2 C3 1.454(3) . ?
C2 C9 1.458(3) . ?
C3 C8 1.347(3) . ?
C3 C4 1.505(3) . ?
C8 C7 1.501(3) . ?
C8 Se1 1.872(2) . ?
C7 C6 1.507(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 C5 1.493(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 C4 1.526(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4A 0.9700 . ?
C9 O2 1.226(3) . ?
C9 O3 1.327(3) . ?
C10 O3 1.447(3) . ?
C10 C11 1.493(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O1 1.216(3) . ?
C12 N1 1.355(3) . ?
C12 C13 1.496(3) . ?
C13 C18 1.385(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(3) . ?
C16 N2 1.471(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 H1 0.81(4) . ?
N2 O5 1.216(3) . ?
N2 O4 1.217(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
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.6(2) . . . . ?
Se1 C1 C2 C3 0.6(3) . . . . ?
N1 C1 C2 C9 1.3(4) . . . . ?
Se1 C1 C2 C9 -178.46(16) . . . . ?
C1 C2 C3 C8 -0.4(3) . . . . ?
C9 C2 C3 C8 178.6(2) . . . . ?
C1 C2 C3 C4 179.7(2) . . . . ?
C9 C2 C3 C4 -1.3(4) . . . . ?
C2 C3 C8 C7 179.5(2) . . . . ?
C4 C3 C8 C7 -0.6(4) . . . . ?
C2 C3 C8 Se1 0.0(3) . . . . ?
C4 C3 C8 Se1 179.89(17) . . . . ?
C3 C8 C7 C6 18.5(4) . . . . ?
Se1 C8 C7 C6 -161.95(19) . . . . ?
C8 C7 C6 C5 -46.2(3) . . . . ?
C7 C6 C5 C4 59.6(3) . . . . ?
C8 C3 C4 C5 10.8(3) . . . . ?
C2 C3 C4 C5 -169.4(2) . . . . ?
C6 C5 C4 C3 -40.2(3) . . . . ?
C1 C2 C9 O2 -2.8(4) . . . . ?
C3 C2 C9 O2 178.4(2) . . . . ?
C1 C2 C9 O3 176.4(2) . . . . ?
C3 C2 C9 O3 -2.5(3) . . . . ?
O1 C12 C13 C18 -178.6(2) . . . . ?
N1 C12 C13 C18 1.4(4) . . . . ?
O1 C12 C13 C14 1.3(4) . . . . ?
N1 C12 C13 C14 -178.8(2) . . . . ?
C18 C13 C14 C15 1.1(4) . . . . ?
C12 C13 C14 C15 -178.7(2) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 -1.5(4) . . . . ?
C14 C15 C16 N2 178.6(2) . . . . ?
C15 C16 C17 C18 1.9(4) . . . . ?
N2 C16 C17 C18 -178.3(2) . . . . ?
C14 C13 C18 C17 -0.7(4) . . . . ?
C12 C13 C18 C17 179.1(2) . . . . ?
C16 C17 C18 C13 -0.7(4) . . . . ?
O1 C12 N1 C1 3.5(4) . . . . ?
C13 C12 N1 C1 -176.5(2) . . . . ?
C2 C1 N1 C12 178.3(2) . . . . ?
Se1 C1 N1 C12 -1.9(3) . . . . ?
C15 C16 N2 O5 -179.5(2) . . . . ?
C17 C16 N2 O5 0.6(3) . . . . ?
C15 C16 N2 O4 0.6(4) . . . . ?
C17 C16 N2 O4 -179.2(2) . . . . ?
O2 C9 O3 C10 -0.1(3) . . . . ?
C2 C9 O3 C10 -179.2(2) . . . . ?
C11 C10 O3 C9 169.5(3) . . . . ?
C2 C1 Se1 C8 -0.48(18) . . . . ?
N1 C1 Se1 C8 179.7(2) . . . . ?
C3 C8 Se1 C1 0.27(18) . . . . ?
C7 C8 Se1 C1 -179.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17279140
2 PubChem 16122189
