#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $
#$Revision: 301791 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/36/2003693.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2003693
loop_
_publ_author_name
'Fong, M. C.'
'Gable, R. W.'
'Schiesser, C. H.'
_publ_section_title
;
 3-Phenyl-1,3(4<i>H</i>)-benzoselenazine-2,4(3<i>H</i>)-dione
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1333
_journal_page_last               1335
_journal_paper_doi               10.1107/S0108270194014563
_journal_volume                  51
_journal_year                    1995
_chemical_formula_sum            'C14 H9 N O2 Se'
_chemical_formula_weight         302.18
_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_type_scat_source           IntTabC
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8054(10)
_cell_length_b                   5.0922(10)
_cell_length_c                   20.0693(13)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      41.7
_cell_measurement_theta_min      26.6
_cell_volume                     1206.5(3)
_diffrn_measurement_device       'Enraf-Nonius CAD-4 MachS'
_diffrn_measurement_method       '\w/2\q '
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3810
_diffrn_reflns_theta_max         75.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.159
_exptl_absorpt_correction_T_max  0.707
_exptl_absorpt_correction_T_min  0.305
_exptl_absorpt_correction_type   'analytical (indexed crystal faces)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.618
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_method
;
F~c~^*^ = kF~c~[1 + 0.001\cF~c~^2^\l^3^/sin(2\q)]
;
_refine_ls_goodness_of_fit_obs   1.123
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2487
_refine_ls_R_factor_obs          0.0333
_refine_ls_shift/esd_max         -0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
w = 1/[\s^2^(F~o~^2^) + (0.0552P)^2^ + 0.3368P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         0.0894
_reflns_number_observed          2427
_reflns_number_total             2487
_reflns_observed_criterion       I>2\s(I)
_cod_data_source_file            kh1013.cif
_cod_data_source_block           kh1013a
_cod_database_code               2003693
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Se 0.06024(3) 0.14766(6) 0.46713(2) 0.05003(14)
O(2) 0.2718(3) 0.3332(7) 0.4667(2) 0.0826(10)
O(4) 0.2456(2) -0.2530(5) 0.29945(13) 0.0557(6)
N 0.2541(2) 0.0236(5) 0.38612(13) 0.0437(6)
C(2) 0.2131(3) 0.1777(7) 0.4379(2) 0.0517(7)
C(4) 0.1948(3) -0.1547(6) 0.34559(13) 0.0408(6)
C(4a) 0.0754(3) -0.2231(5) 0.35889(14) 0.0400(6)
C(5) 0.0287(3) -0.4185(7) 0.3181(2) 0.0480(7)
C(6) -0.0822(3) -0.4979(8) 0.3254(2) 0.0559(8)
C(7) -0.1481(3) -0.3832(9) 0.3741(2) 0.0620(9)
C(8) -0.1049(3) -0.1913(7) 0.4150(2) 0.0546(8)
C(8a) 0.0071(3) -0.1112(6) 0.4074(2) 0.0422(6)
C(9) 0.3746(3) 0.0484(7) 0.3727(2) 0.0457(7)
C(10) 0.4136(3) 0.2365(8) 0.3283(2) 0.0597(9)
C(11) 0.5292(4) 0.2487(9) 0.3160(2) 0.0688(11)
C(12) 0.6029(3) 0.0849(8) 0.3475(2) 0.0643(10)
C(13) 0.5624(3) -0.1015(9) 0.3918(2) 0.0654(9)
C(14) 0.4479(3) -0.1194(7) 0.4042(2) 0.0570(8)
H(5) 0.0734(3) -0.4960(7) 0.2854(2) 0.062(12)
H(6) -0.1122(3) -0.6274(8) 0.2979(2) 0.061(11)
H(7) -0.2230(3) -0.4365(9) 0.3794(2) 0.14(3)
H(8) -0.1503(3) -0.1152(7) 0.4476(2) 0.077(14)
H(10) 0.3637(3) 0.3510(8) 0.3073(2) 0.067(13)
H(11) 0.5568(4) 0.3712(9) 0.2858(2) 0.11(2)
H(12) 0.6802(3) 0.0979(8) 0.3393(2) 0.11(2)
H(13) 0.6125(3) -0.2144(9) 0.4132(2) 0.08(2)
H(14) 0.4204(3) -0.2447(7) 0.4338(2) 0.072(13)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(8a) Se C(2) 100.13(14) yes
C(2) N C(4) 128.6(3) yes
C(2) N C(9) 115.5(3) yes
C(4) N C(9) 115.9(3) yes
O(2) C(2) N 122.0(3) yes
O(2) C(2) Se 117.0(3) yes
N C(2) Se 121.0(2) yes
O(4) C(4) N 117.6(3) yes
O(4) C(4) C(4a) 120.9(3) yes
N C(4) C(4a) 121.5(2) yes
C(8a) C(4a) C(5) 118.2(3) yes
C(4a) C(8a) Se 122.6(2) yes
C(8) C(8a) Se 116.8(2) yes
C(14) C(9) C(10) 121.2(3) yes
C(14) C(9) N 118.6(3) yes
C(10) C(9) N 120.2(3) yes
C(8a) C(4a) C(4) 125.8(3) no
C(5) C(4a) C(4) 116.0(3) no
C(6) C(5) C(4a) 121.3(3) no
C(5) C(6) C(7) 119.2(3) no
C(8) C(7) C(6) 121.0(3) no
C(7) C(8) C(8a) 119.7(3) no
C(4a) C(8a) C(8) 120.6(3) no
C(9) C(10) C(11) 118.1(4) no
C(12) C(11) C(10) 121.3(4) no
C(11) C(12) C(13) 119.8(4) no
C(14) C(13) C(12) 120.0(4) no
C(9) C(14) C(13) 119.7(3) no
C(6) C(5) H(5) 119.3(2) no
C(4a) C(5) H(5) 119.3(2) no
C(5) C(6) H(6) 120.4(2) no
C(7) C(6) H(6) 120.4(2) no
C(8) C(7) H(7) 119.5(2) no
C(6) C(7) H(7) 119.5(2) no
C(7) C(8) H(8) 120.1(2) no
C(8a) C(8) H(8) 120.1(2) no
C(9) C(10) H(10) 121.0(2) no
C(11) C(10) H(10) 121.0(3) no
C(12) C(11) H(11) 119.4(3) no
C(10) C(11) H(11) 119.4(3) no
C(11) C(12) H(12) 120.1(3) no
C(13) C(12) H(12) 120.1(2) no
C(14) C(13) H(13) 120.0(2) no
C(12) C(13) H(13) 120.0(2) no
C(9) C(14) H(14) 120.2(2) no
C(13) C(14) H(14) 120.2(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Se C(8a) 1.889(3) yes
Se C(2) 1.903(3) yes
O(2) C(2) 1.200(4) yes
O(4) C(4) 1.211(4) yes
N C(2) 1.390(4) yes
N C(4) 1.406(4) yes
N C(9) 1.454(4) yes
C(4) C(4a) 1.476(4) yes
C(4a) C(8a) 1.387(4) no
C(4a) C(5) 1.402(4) no
C(5) C(6) 1.378(5) no
C(6) C(7) 1.379(5) no
C(7) C(8) 1.374(5) no
C(8) C(8a) 1.392(5) no
C(9) C(14) 1.370(5) no
C(9) C(10) 1.387(5) no
C(10) C(11) 1.388(6) no
C(11) C(12) 1.361(7) no
C(12) C(13) 1.386(6) no
C(13) C(14) 1.377(5) no
C(5) H(5) 0.93 no
C(6) H(6) 0.93 no
C(7) H(7) 0.93 no
C(8) H(8) 0.93 no
C(10) H(10) 0.93 no
C(11) H(11) 0.93 no
C(12) H(12) 0.93 no
C(13) H(13) 0.93 no
C(14) H(14) 0.93 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11087960