#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/10/7151098.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_7151098
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 H19 N O3 Se'
_chemical_formula_weight         376.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 93.498(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0161(9)
_cell_length_b                   10.6336(13)
_cell_length_c                   18.746(2)
_cell_measurement_reflns_used    4731
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.55
_cell_volume                     1594.9(3)
_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      130(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9581
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    2.369
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0304
_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)+(0.0539P)²+0.0984P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0831
_reflns_number_gt                3177
_reflns_number_total             3629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B700812K.txt
_cod_data_source_block           jmwka1lt
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7151098
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C6' C 0.0294(12) 1.1267(7) 0.2264(4) 0.036(2) Uani 0.368(10) 1 d P A 1
H6'1 H 0.1282 1.1757 0.2403 0.044 Uiso 0.368(10) 1 calc PR A 1
H6'2 H -0.0424 1.1260 0.2662 0.044 Uiso 0.368(10) 1 calc PR A 1
C5' C -0.0611(12) 1.1863(8) 0.1629(4) 0.0310(17) Uani 0.368(10) 1 d P A 1
H5'1 H -0.1044 1.2674 0.1765 0.037 Uiso 0.368(10) 1 calc PR A 1
H5'2 H -0.1551 1.1338 0.1469 0.037 Uiso 0.368(10) 1 calc PR A 1
C6 C -0.0576(7) 1.1014(4) 0.2078(2) 0.0315(11) Uani 0.632(10) 1 d P A 2
H6A H -0.1557 1.0724 0.1797 0.038 Uiso 0.632(10) 1 calc PR A 2
H6B H -0.0900 1.1176 0.2560 0.038 Uiso 0.632(10) 1 calc PR A 2
C5 C 0.0061(7) 1.2222(4) 0.1757(2) 0.0321(10) Uani 0.632(10) 1 d P A 2
H5A H -0.0807 1.2858 0.1761 0.038 Uiso 0.632(10) 1 calc PR A 2
H5B H 0.1016 1.2524 0.2051 0.038 Uiso 0.632(10) 1 calc PR A 2
C1 C 0.2847(2) 0.92572(16) 0.02340(9) 0.0238(3) Uani 1 1 d . A .
C2 C 0.2201(2) 1.04566(16) 0.02216(9) 0.0233(3) Uani 1 1 d . . .
C3 C 0.1423(2) 1.08075(16) 0.08741(9) 0.0239(3) Uani 1 1 d . A .
C8 C 0.1487(2) 0.98986(17) 0.13750(9) 0.0281(4) Uani 1 1 d . A .
C7 C 0.0780(3) 0.9982(2) 0.20979(11) 0.0361(5) Uani 1 1 d . . .
C4 C 0.0565(2) 1.20433(19) 0.10011(10) 0.0291(4) Uani 1 1 d . . .
C9 C 0.2366(2) 1.12363(17) -0.04147(9) 0.0244(3) Uani 1 1 d . . .
C10 C 0.1935(3) 1.32145(18) -0.09654(10) 0.0347(4) Uani 1 1 d . . .
H10A H 0.1371 1.2846 -0.1388 0.042 Uiso 1 1 calc R . .
H10B H 0.3102 1.3339 -0.1056 0.042 Uiso 1 1 calc R . .
C11 C 0.1139(3) 1.44393(19) -0.07893(12) 0.0446(5) Uani 1 1 d . . .
H11A H -0.0012 1.4301 -0.0699 0.067 Uiso 1 1 calc R . .
H11B H 0.1207 1.5008 -0.1184 0.067 Uiso 1 1 calc R . .
H11C H 0.1712 1.4795 -0.0372 0.067 Uiso 1 1 calc R . .
C12 C 0.4163(2) 0.74983(17) -0.03320(10) 0.0283(4) Uani 1 1 d . . .
C13 C 0.4834(2) 0.70568(18) -0.10132(9) 0.0272(4) Uani 1 1 d . . .
C14 C 0.5371(2) 0.58163(18) -0.10363(10) 0.0326(4) Uani 1 1 d . . .
H14 H 0.5337 0.5311 -0.0633 0.039 Uiso 1 1 calc R . .
C15 C 0.5958(3) 0.53295(19) -0.16611(11) 0.0380(5) Uani 1 1 d . . .
H15 H 0.6335 0.4503 -0.1671 0.046 Uiso 1 1 calc R . .
C16 C 0.5985(3) 0.6060(2) -0.22631(11) 0.0367(4) Uani 1 1 d . . .
H16 H 0.6352 0.5723 -0.2684 0.044 Uiso 1 1 calc R . .
C17 C 0.5466(2) 0.7296(2) -0.22428(10) 0.0349(4) Uani 1 1 d . . .
H17 H 0.5490 0.7792 -0.2651 0.042 Uiso 1 1 calc R . .
C18 C 0.4910(2) 0.78024(19) -0.16191(10) 0.0317(4) Uani 1 1 d . . .
H18 H 0.4587 0.8642 -0.1606 0.038 Uiso 1 1 calc R . .
N1 N 0.3641(2) 0.87124(15) -0.03191(8) 0.0257(3) Uani 1 1 d . . .
O1 O 0.40489(19) 0.68107(13) 0.01876(7) 0.0366(3) Uani 1 1 d . . .
O2 O 0.29961(17) 1.08795(12) -0.09574(6) 0.0297(3) Uani 1 1 d . . .
O3 O 0.17842(17) 1.23995(12) -0.03530(6) 0.0301(3) Uani 1 1 d . . .
Se Se 0.25570(2) 0.843264(17) 0.108982(9) 0.02972(9) Uani 1 1 d . . .
H1 H 0.369(3) 0.921(2) -0.0668(12) 0.033(6) Uiso 1 1 d . . .
H4B H 0.131(3) 1.279(2) 0.0928(12) 0.040(6) Uiso 1 1 d . . .
H4A H -0.035(3) 1.220(2) 0.0617(12) 0.035(6) Uiso 1 1 d . . .
H7B H 0.010(3) 0.926(3) 0.2148(15) 0.062(8) Uiso 1 1 d . . .
H7A H 0.157(4) 0.996(2) 0.2411(15) 0.065(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
C7 C6' C5' 110.5(7) . . ?
C7 C6' H6'1 109.6 . . ?
C5' C6' H6'1 109.6 . . ?
C7 C6' H6'2 109.6 . . ?
C5' C6' H6'2 109.6 . . ?
H6'1 C6' H6'2 108.1 . . ?
C6' C5' C4 111.4(7) . . ?
C6' C5' H5'1 109.3 . . ?
C4 C5' H5'1 109.3 . . ?
C6' C5' H5'2 109.3 . . ?
C4 C5' H5'2 109.3 . . ?
H5'1 C5' H5'2 108.0 . . ?
C5 C6 C7 110.9(4) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C4 C5 C6 112.4(4) . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C2 C1 N1 124.61(15) . . ?
C2 C1 Se 112.68(12) . . ?
N1 C1 Se 122.71(13) . . ?
C1 C2 C3 113.80(15) . . ?
C1 C2 C9 119.04(15) . . ?
C3 C2 C9 127.15(15) . . ?
C8 C3 C2 113.73(16) . . ?
C8 C3 C4 120.89(16) . . ?
C2 C3 C4 125.36(15) . . ?
C3 C8 C7 125.90(17) . . ?
C3 C8 Se 113.39(13) . . ?
C7 C8 Se 120.70(14) . . ?
C6' C7 C8 111.5(3) . . ?
C6' C7 C6 31.0(3) . . ?
C8 C7 C6 108.92(19) . . ?
C6' C7 H7B 125.0(17) . . ?
C8 C7 H7B 106.9(16) . . ?
C6 C7 H7B 99.8(17) . . ?
C6' C7 H7A 94.1(19) . . ?
C8 C7 H7A 108.8(19) . . ?
C6 C7 H7A 122.2(19) . . ?
H7B C7 H7A 109(2) . . ?
C3 C4 C5 114.1(2) . . ?
C3 C4 C5' 108.3(3) . . ?
C5 C4 C5' 25.9(2) . . ?
C3 C4 H4B 112.6(13) . . ?
C5 C4 H4B 102.9(13) . . ?
C5' C4 H4B 126.1(13) . . ?
C3 C4 H4A 110.4(13) . . ?
C5 C4 H4A 115.3(12) . . ?
C5' C4 H4A 96.6(13) . . ?
H4B C4 H4A 100.4(18) . . ?
O2 C9 O3 121.72(16) . . ?
O2 C9 C2 124.32(16) . . ?
O3 C9 C2 113.95(14) . . ?
O3 C10 C11 106.77(15) . . ?
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 121.00(17) . . ?
O1 C12 C13 122.74(17) . . ?
N1 C12 C13 116.24(16) . . ?
C14 C13 C18 119.18(17) . . ?
C14 C13 C12 117.01(16) . . ?
C18 C13 C12 123.79(17) . . ?
C15 C14 C13 120.11(18) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 120.42(19) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.78(17) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 120.46(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.00(19) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C12 N1 C1 124.78(16) . . ?
C12 N1 H1 123.5(15) . . ?
C1 N1 H1 111.5(14) . . ?
C9 O3 C10 116.15(14) . . ?
C1 Se C8 86.40(8) . . ?
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
C6' C7 1.461(7) . ?
C6' C5' 1.496(12) . ?
C6' H6'1 0.9700 . ?
C6' H6'2 0.9700 . ?
C5' C4 1.564(7) . ?
C5' H5'1 0.9700 . ?
C5' H5'2 0.9700 . ?
C6 C5 1.521(7) . ?
C6 C7 1.544(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 C4 1.509(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C1 C2 1.376(2) . ?
C1 N1 1.377(2) . ?
C1 Se 1.8554(17) . ?
C2 C3 1.455(2) . ?
C2 C9 1.465(2) . ?
C3 C8 1.346(2) . ?
C3 C4 1.509(3) . ?
C8 C7 1.503(2) . ?
C8 Se 1.8728(18) . ?
C7 H7B 0.95(3) . ?
C7 H7A 0.83(3) . ?
C4 H4B 1.01(2) . ?
C4 H4A 1.01(2) . ?
C9 O2 1.223(2) . ?
C9 O3 1.329(2) . ?
C10 O3 1.449(2) . ?
C10 C11 1.496(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O1 1.226(2) . ?
C12 N1 1.358(2) . ?
C12 C13 1.492(2) . ?
C13 C14 1.389(3) . ?
C13 C18 1.389(3) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 H1 0.84(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 16122190
