#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2005307.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_2005307
loop_
_publ_author_name
'Fong, M. C.'
'Gable, R. W.'
'Schiesser, C. H.'
_publ_section_title
;
 <i>N</i>-Phenyl-2-(triphenylstannylseleno)benzamide and
 2-Methylseleno-<i>N</i>-phenylbenzamide
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1886
_journal_page_last               1889
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C14 H13 N1 O1 Se1'
_chemical_formula_sum            'C14 H13 N O Se'
_chemical_formula_weight         290.22
_chemical_name_systematic
;
 2-methylseleno-N-phenylbenzamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.777(2)
_cell_length_b                   16.692(2)
_cell_length_c                   15.8203(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      34.6
_cell_measurement_theta_min      18.8
_cell_volume                     2581.8(7)
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD-4 MachS'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  none
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'CuK\a (nickel filtered)'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3400
_diffrn_reflns_theta_max         74.92
_diffrn_reflns_theta_min         5.30
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.794
_exptl_absorpt_correction_T_max  0.8599
_exptl_absorpt_correction_T_min  0.3036
_exptl_absorpt_correction_type
'Gaussian integration from crystal shape (SHELX76; Sheldrick, 1976)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      none
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.425
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.049
_refine_ls_goodness_of_fit_obs   1.080
_refine_ls_hydrogen_treatment
;
For H(N), all coordinates refined; other H atoms riding with all
parameters refined
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2659
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_restrained_S_obs      1.080
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_obs          0.0290
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0366P)^2^ + 1.0801P]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.0795
_refine_ls_wR_factor_obs         0.0731
_reflns_number_observed          2149
_reflns_number_total             2659
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ta1069.cif
_[local]_cod_data_source_block   csch_5
_[local]_cod_chemical_formula_sum_orig 'C14 H13 N1 O1 Se1'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_contact_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (2
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2005307
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'
'-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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Se 0.0515(2) 0.0618(2) 0.0528(2) -0.01016(12) -0.00519(11) 0.00159(12)
O 0.0338(8) 0.0798(12) 0.0727(11) -0.0139(8) -0.0064(8) 0.0157(10)
N 0.0275(9) 0.0521(10) 0.0593(11) -0.0078(8) 0.0017(9) 0.0047(9)
C1 0.0357(10) 0.0454(11) 0.0514(12) 0.0026(9) 0.0037(9) -0.0046(10)
C2 0.0330(10) 0.0462(11) 0.0496(11) -0.0015(9) 0.0044(9) -0.0048(9)
C3 0.0533(14) 0.0574(13) 0.0552(14) -0.0072(11) -0.0011(12) -0.0079(11)
C4 0.072(2) 0.0540(14) 0.074(2) -0.0198(13) -0.0037(15) -0.0098(13)
C5 0.067(2) 0.0446(12) 0.082(2) -0.0086(12) 0.0029(15) 0.0018(13)
C6 0.0517(13) 0.0498(12) 0.0611(14) 0.0040(11) 0.0021(11) 0.0038(11)
C7 0.0325(10) 0.0525(11) 0.0463(11) -0.0038(9) 0.0032(9) -0.0047(10)
C8 0.0414(11) 0.0458(11) 0.0477(11) -0.0062(9) 0.0063(10) -0.0045(10)
C9 0.0447(13) 0.0621(14) 0.0605(15) -0.0146(11) 0.0057(11) 0.0016(12)
C10 0.065(2) 0.072(2) 0.071(2) -0.0258(15) 0.0155(14) 0.0031(15)
C11 0.091(2) 0.0565(15) 0.074(2) -0.011(2) 0.014(2) 0.0123(14)
C12 0.069(2) 0.064(2) 0.088(2) 0.0065(14) 0.006(2) 0.0197(15)
C13 0.0466(14) 0.0581(14) 0.075(2) -0.0016(11) 0.0054(12) 0.0091(13)
C14 0.114(3) 0.091(2) 0.057(2) -0.031(2) -0.019(2) 0.010(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Se 0.04443(3) 0.21728(2) 0.05502(2) 0.05538(11) Uani d . 1 Se
O 0.0492(2) 0.16221(11) 0.22408(12) 0.0621(5) Uani d . 1 O
N 0.2559(2) 0.14000(12) 0.28273(13) 0.0463(4) Uani d . 1 N
C1 0.1760(2) 0.28094(13) 0.11507(15) 0.0442(5) Uani d . 1 C
C2 0.2232(2) 0.25693(13) 0.19475(14) 0.0429(5) Uani d . 1 C
C3 0.3160(3) 0.3049(2) 0.2381(2) 0.0553(6) Uani d . 1 C
H3 0.3474(3) 0.2891(2) 0.2910(2) 0.063(8) Uiso calc R 1 H
C4 0.3620(3) 0.3760(2) 0.2032(2) 0.0666(7) Uani d . 1 C
H4 0.4237(3) 0.4079(2) 0.2327(2) 0.085(10) Uiso calc R 1 H
C5 0.3163(3) 0.3993(2) 0.1248(2) 0.0644(7) Uani d . 1 C
H5 0.3471(3) 0.4472(2) 0.1015(2) 0.074(9) Uiso calc R 1 H
C6 0.2254(3) 0.35232(14) 0.0807(2) 0.0542(6) Uani d . 1 C
H6 0.1964(3) 0.36832(14) 0.0273(2) 0.062(8) Uiso calc R 1 H
C7 0.1687(2) 0.18249(14) 0.23479(14) 0.0438(5) Uani d . 1 C
C8 0.2294(2) 0.07190(13) 0.33304(14) 0.0450(5) Uani d . 1 C
C9 0.0989(3) 0.0437(2) 0.3504(2) 0.0558(6) Uani d . 1 C
H9 0.0227(3) 0.0685(2) 0.3269(2) 0.056(7) Uiso calc R 1 H
C10 0.0834(3) -0.0219(2) 0.4035(2) 0.0696(8) Uani d . 1 C
H10 -0.0041(3) -0.0405(2) 0.4155(2) 0.079(9) Uiso calc R 1 H
C11 0.1936(4) -0.0598(2) 0.4384(2) 0.0739(8) Uani d . 1 C
H11 0.1813(4) -0.1039(2) 0.4734(2) 0.081(9) Uiso calc R 1 H
C12 0.3228(3) -0.0320(2) 0.4211(2) 0.0733(8) Uani d . 1 C
H12 0.3985(3) -0.0572(2) 0.4448(2) 0.090(11) Uiso calc R 1 H
C13 0.3404(3) 0.0333(2) 0.3687(2) 0.0600(6) Uani d . 1 C
H13 0.4283(3) 0.0517(2) 0.3572(2) 0.059(8) Uiso calc R 1 H
C14 0.0722(5) 0.2586(3) -0.0579(2) 0.0875(11) Uani d . 1 C
H14A 0.0117(5) 0.2317(3) -0.0964(2) 0.138(16) Uiso calc R 1 H
H14B 0.1652(5) 0.2495(3) -0.0748(2) 0.139(18) Uiso calc R 1 H
H14C 0.0534(5) 0.3150(3) -0.0586(2) 0.122(16) Uiso calc R 1 H
H(N) 0.325(3) 0.1528(14) 0.281(2) 0.043(7) Uiso d . 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 '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_publ_flag
C1 Se C14 99.55(13) y
C7 N C8 128.8(2) y
C7 N H(N) 115(2) ?
C8 N H(N) 116(2) ?
C6 C1 C2 118.7(2) ?
C6 C1 Se 120.8(2) ?
C2 C1 Se 120.5(2) ?
C3 C2 C1 119.6(2) ?
C3 C2 C7 120.2(2) ?
C1 C2 C7 120.1(2) ?
C4 C3 C2 120.6(2) ?
C4 C3 H3 119.7(2) ?
C2 C3 H3 119.71(14) ?
C5 C4 C3 119.8(3) ?
C5 C4 H4 120.1(2) ?
C3 C4 H4 120.1(2) ?
C4 C5 C6 120.4(2) ?
C4 C5 H5 119.8(2) ?
C6 C5 H5 119.8(2) ?
C5 C6 C1 120.9(2) ?
C5 C6 H6 119.6(2) ?
C1 C6 H6 119.57(15) ?
O C7 N 122.4(2) y
O C7 C2 120.7(2) y
N C7 C2 116.9(2) y
C13 C8 C9 118.9(2) ?
C13 C8 N 117.4(2) ?
C9 C8 N 123.6(2) ?
C8 C9 C10 119.2(3) ?
C8 C9 H9 120.41(15) ?
C10 C9 H9 120.4(2) ?
C11 C10 C9 121.6(3) ?
C11 C10 H10 119.2(2) ?
C9 C10 H10 119.2(2) ?
C10 C11 C12 119.3(3) ?
C10 C11 H11 120.4(2) ?
C12 C11 H11 120.4(2) ?
C11 C12 C13 120.1(3) ?
C11 C12 H12 120.0(2) ?
C13 C12 H12 120.0(2) ?
C12 C13 C8 121.0(2) ?
C12 C13 H13 119.5(2) ?
C8 C13 H13 119.51(14) ?
Se C14 H14A 109.47(11) ?
Se C14 H14B 109.47(14) ?
H14A C14 H14B 109.5 ?
Se C14 H14C 109.47(14) ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Se C1 1.920(2) y
Se C14 1.935(3) y
O C7 1.228(3) y
N C7 1.343(3) y
N C8 1.412(3) y
N H(N) 0.71(2) ?
C1 C6 1.396(3) ?
C1 C2 1.401(3) ?
C2 C3 1.391(3) ?
C2 C7 1.493(3) ?
C3 C4 1.384(4) ?
C3 H3 0.93 ?
C4 C5 1.374(4) ?
C4 H4 0.93 ?
C5 C6 1.376(4) ?
C5 H5 0.93 ?
C6 H6 0.93 ?
C8 C13 1.383(3) ?
C8 C9 1.387(3) ?
C9 C10 1.388(4) ?
C9 H9 0.93 ?
C10 C11 1.366(4) ?
C10 H10 0.93 ?
C11 C12 1.373(4) ?
C11 H11 0.93 ?
C12 C13 1.380(4) ?
C12 H12 0.93 ?
C13 H13 0.93 ?
C14 H14A 0.96 ?
C14 H14B 0.96 ?
C14 H14C 0.96 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
Se O 2.829(2) y
Se N 4.349(2) y
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_publ_flag
C14 Se C1 C6 19.8(2) y
C14 Se C1 C2 -160.9(2) y
C6 C1 C2 C3 0.9(3) ?
Se C1 C2 C3 -178.4(2) ?
C6 C1 C2 C7 177.7(2) ?
Se C1 C2 C7 -1.6(3) ?
C1 C2 C3 C4 0.0(4) ?
C7 C2 C3 C4 -176.8(2) ?
C2 C3 C4 C5 -0.4(4) ?
C3 C4 C5 C6 -0.2(4) ?
C4 C5 C6 C1 1.1(4) ?
C2 C1 C6 C5 -1.5(3) ?
Se C1 C6 C5 177.9(2) ?
C8 N C7 O -5.4(4) y
C8 N C7 C2 174.2(2) y
C3 C2 C7 O 142.6(2) y
C1 C2 C7 O -34.2(3) y
C3 C2 C7 N -37.0(3) y
C1 C2 C7 N 146.2(2) y
C7 N C8 C13 172.5(2) y
C7 N C8 C9 -9.6(4) y
C13 C8 C9 C10 0.4(4) ?
N C8 C9 C10 -177.4(2) ?
C8 C9 C10 C11 -0.5(4) ?
C9 C10 C11 C12 0.5(5) ?
C10 C11 C12 C13 -0.3(5) ?
C11 C12 C13 C8 0.2(5) ?
C9 C8 C13 C12 -0.3(4) ?
N C8 C13 C12 177.7(3) ?