#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:04:54 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178419 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/40/4024017.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_4024017
loop_
_publ_author_name
'Devarajulu Sureshkumar'
'Venkataraman Ganesh'
'Srinivasan Chandrasekaran'
_publ_contact_author_address
; 
Department of Organic Chemistry
Indian Institute of Science
Bangaloe 560012, Karnataka
India
;
_publ_contact_author_email       scn@orgchem.iisc.ernet.in
_publ_contact_author_fax         '+91 80 23602423'
_publ_contact_author_name        'Prof. Srinivasan Chandrasekaran'
_publ_contact_author_phone       '+91 80 22932404'
_publ_section_title
;
 Conformationally Locked Bridged Bicyclic Diselenides: Synthesis,
 Structure, Se···O Interaction, and Theoretical Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5313
_journal_page_last               5319
_journal_paper_doi               10.1021/jo070705k
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C15 H21 N O3 S Se2'
_chemical_formula_sum            'C15 H21 N O3 S Se2'
_chemical_formula_weight         453.31
_chemical_melting_point          456.15
_chemical_name_common            'locked diselenide'
_chemical_name_systematic
;
 ?
;
_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                93.496(3)
_cell_angle_beta                 97.839(3)
_cell_angle_gamma                108.762(3)
_cell_formula_units_Z            2
_cell_length_a                   6.2232(13)
_cell_length_b                   7.9631(16)
_cell_length_c                   18.610(4)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.11
_cell_volume                     859.6(3)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω 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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8193
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.11
_exptl_absorpt_coefficient_mu    4.433
_exptl_absorpt_correction_T_max  0.8088
_exptl_absorpt_correction_T_min  0.4036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.167
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0704P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2282
_reflns_number_total             3019
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo070705ksi20070405_075852_07.cif
_cod_data_source_block           compound19
_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.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '183 deg' was changed to '456.15' -
it was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4024017
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
Se1 Se 0.73772(10) 0.72054(8) 0.42735(3) 0.0465(2) Uani 1 1 d . . .
Se2 Se 0.58524(10) 0.40749(8) 0.40321(4) 0.0496(2) Uani 1 1 d . . .
S1 S 1.2168(3) 0.93641(18) 0.20765(8) 0.0453(4) Uani 1 1 d . . .
C4 C 0.8465(9) 0.3985(7) 0.3521(3) 0.0372(12) Uani 1 1 d . . .
C2 C 1.0057(9) 0.7324(7) 0.3765(3) 0.0348(12) Uani 1 1 d . . .
C3 C 1.0530(8) 0.5586(6) 0.3861(3) 0.0340(12) Uani 1 1 d . . .
H3A H 1.1847 0.5588 0.3636 0.041 Uiso 1 1 calc R . .
H3B H 1.0902 0.5494 0.4378 0.041 Uiso 1 1 calc R . .
C1 C 0.9379(9) 0.7497(7) 0.2956(3) 0.0363(12) Uani 1 1 d . . .
H1 H 0.8872 0.8539 0.2924 0.044 Uiso 1 1 calc R . .
N1 N 1.1444(8) 0.7825(6) 0.2609(2) 0.0411(11) Uani 1 1 d . . .
O1 O 0.9653(8) 0.4035(5) 0.2327(2) 0.0575(11) Uani 1 1 d . . .
C5 C 0.7808(10) 0.4102(7) 0.2708(3) 0.0470(15) Uani 1 1 d . . .
H5 H 0.6409 0.3103 0.2506 0.056 Uiso 1 1 calc R . .
O3 O 1.1775(8) 1.0895(5) 0.2397(2) 0.0567(11) Uani 1 1 d . . .
C9 C 1.0310(10) 0.8651(7) 0.1227(3) 0.0443(14) Uani 1 1 d . . .
C7 C 1.2054(9) 0.8945(7) 0.4154(3) 0.0444(14) Uani 1 1 d . . .
H7A H 1.2410 0.8772 0.4656 0.053 Uiso 1 1 calc R . .
H7B H 1.1624 0.9997 0.4126 0.053 Uiso 1 1 calc R . .
H7C H 1.3380 0.9083 0.3923 0.053 Uiso 1 1 calc R . .
O2 O 1.4415(7) 0.9489(6) 0.1950(2) 0.0614(12) Uani 1 1 d . . .
C8 C 0.8810(11) 0.2209(7) 0.3652(3) 0.0491(15) Uani 1 1 d . . .
H8A H 1.0093 0.2125 0.3436 0.059 Uiso 1 1 calc R . .
H8B H 0.7447 0.1246 0.3434 0.059 Uiso 1 1 calc R . .
H8C H 0.9107 0.2140 0.4167 0.059 Uiso 1 1 calc R . .
C6 C 0.7414(10) 0.5863(7) 0.2573(3) 0.0432(14) Uani 1 1 d . . .
H6A H 0.7215 0.5951 0.2052 0.052 Uiso 1 1 calc R . .
H6B H 0.6002 0.5858 0.2740 0.052 Uiso 1 1 calc R . .
C10 C 0.8399(12) 0.9116(10) 0.1086(4) 0.0668(19) Uani 1 1 d . . .
H10 H 0.8044 0.9833 0.1432 0.080 Uiso 1 1 calc R . .
C14 C 1.0799(14) 0.7598(10) 0.0698(4) 0.071(2) Uani 1 1 d . . .
H14 H 1.2107 0.7268 0.0789 0.086 Uiso 1 1 calc R . .
C11 C 0.6992(14) 0.8513(12) 0.0422(5) 0.082(2) Uani 1 1 d . . .
H11 H 0.5671 0.8825 0.0331 0.098 Uiso 1 1 calc R . .
C12 C 0.7436(15) 0.7488(10) -0.0103(4) 0.074(2) Uani 1 1 d . . .
C13 C 0.9379(16) 0.7044(11) 0.0047(4) 0.086(2) Uani 1 1 d . . .
H13 H 0.9738 0.6345 -0.0305 0.104 Uiso 1 1 calc R . .
C15 C 0.5820(17) 0.6835(12) -0.0821(5) 0.116(4) Uani 1 1 d . . .
H15A H 0.5240 0.7759 -0.0973 0.139 Uiso 1 1 calc R . .
H15B H 0.4561 0.5802 -0.0763 0.139 Uiso 1 1 calc R . .
H15C H 0.6633 0.6528 -0.1183 0.139 Uiso 1 1 calc R . .
H1N H 1.1477 0.6826 0.2416 0.043(16) Uiso 1 1 d R . .
H1O H 0.9969 0.2950 0.2428 0.14(4) Uiso 1 1 d 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'
S S 0.1246 0.1234 '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 Se1 Se2 92.28(15) . . ?
C4 Se2 Se1 92.11(15) . . ?
O2 S1 O3 119.7(3) . . ?
O2 S1 N1 106.4(3) . . ?
O3 S1 N1 106.9(2) . . ?
O2 S1 C9 107.2(3) . . ?
O3 S1 C9 107.6(3) . . ?
N1 S1 C9 108.7(3) . . ?
C3 C4 C8 112.9(5) . . ?
C3 C4 C5 110.8(4) . . ?
C8 C4 C5 111.5(5) . . ?
C3 C4 Se2 106.4(3) . . ?
C8 C4 Se2 106.2(4) . . ?
C5 C4 Se2 108.8(4) . . ?
C3 C2 C7 112.0(4) . . ?
C3 C2 C1 111.2(4) . . ?
C7 C2 C1 112.7(4) . . ?
C3 C2 Se1 106.0(3) . . ?
C7 C2 Se1 106.0(4) . . ?
C1 C2 Se1 108.5(3) . . ?
C4 C3 C2 111.3(4) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C1 C6 111.8(4) . . ?
N1 C1 C2 108.0(4) . . ?
C6 C1 C2 112.2(4) . . ?
N1 C1 H1 108.2 . . ?
C6 C1 H1 108.2 . . ?
C2 C1 H1 108.2 . . ?
C1 N1 S1 122.4(4) . . ?
C1 N1 H1N 109.2 . . ?
S1 N1 H1N 111.0 . . ?
C5 O1 H1O 107.3 . . ?
O1 C5 C4 109.9(5) . . ?
O1 C5 C6 106.5(5) . . ?
C4 C5 C6 111.8(4) . . ?
O1 C5 H5 109.5 . . ?
C4 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C10 C9 C14 119.1(6) . . ?
C10 C9 S1 120.9(5) . . ?
C14 C9 S1 119.9(5) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C6 C5 113.3(4) . . ?
C1 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C1 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C9 C10 C11 118.9(7) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C13 C14 C9 120.2(7) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C12 C11 C10 123.1(8) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 117.2(7) . . ?
C11 C12 C15 121.2(9) . . ?
C13 C12 C15 121.6(9) . . ?
C14 C13 C12 121.5(8) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
Se1 C2 2.007(5) . ?
Se1 Se2 2.3542(9) . ?
Se2 C4 2.010(5) . ?
S1 O2 1.422(4) . ?
S1 O3 1.429(4) . ?
S1 N1 1.613(5) . ?
S1 C9 1.768(6) . ?
C4 C3 1.517(7) . ?
C4 C8 1.526(7) . ?
C4 C5 1.529(8) . ?
C2 C3 1.521(7) . ?
C2 C7 1.531(7) . ?
C2 C1 1.534(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1 N1 1.472(7) . ?
C1 C6 1.524(7) . ?
C1 H1 0.9800 . ?
N1 H1N 0.8607 . ?
O1 C5 1.443(7) . ?
O1 H1O 0.9693 . ?
C5 C6 1.529(7) . ?
C5 H5 0.9800 . ?
C9 C10 1.353(8) . ?
C9 C14 1.382(9) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 C11 1.373(10) . ?
C10 H10 0.9300 . ?
C14 C13 1.355(10) . ?
C14 H14 0.9300 . ?
C11 C12 1.349(11) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(11) . ?
C12 C15 1.510(10) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
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
C2 Se1 Se2 C4 0.9(2) . . . . ?
Se1 Se2 C4 C3 28.6(3) . . . . ?
Se1 Se2 C4 C8 149.1(4) . . . . ?
Se1 Se2 C4 C5 -90.8(3) . . . . ?
Se2 Se1 C2 C3 -30.2(3) . . . . ?
Se2 Se1 C2 C7 -149.3(3) . . . . ?
Se2 Se1 C2 C1 89.4(3) . . . . ?
C8 C4 C3 C2 -176.1(4) . . . . ?
C5 C4 C3 C2 58.2(6) . . . . ?
Se2 C4 C3 C2 -59.9(5) . . . . ?
C7 C2 C3 C4 175.7(4) . . . . ?
C1 C2 C3 C4 -57.1(6) . . . . ?
Se1 C2 C3 C4 60.7(5) . . . . ?
C3 C2 C1 N1 -71.3(5) . . . . ?
C7 C2 C1 N1 55.4(5) . . . . ?
Se1 C2 C1 N1 172.5(3) . . . . ?
C3 C2 C1 C6 52.4(6) . . . . ?
C7 C2 C1 C6 179.2(5) . . . . ?
Se1 C2 C1 C6 -63.8(5) . . . . ?
C6 C1 N1 S1 102.7(5) . . . . ?
C2 C1 N1 S1 -133.3(4) . . . . ?
O2 S1 N1 C1 170.2(4) . . . . ?
O3 S1 N1 C1 41.2(5) . . . . ?
C9 S1 N1 C1 -74.6(5) . . . . ?
C3 C4 C5 O1 63.5(5) . . . . ?
C8 C4 C5 O1 -63.0(6) . . . . ?
Se2 C4 C5 O1 -179.8(3) . . . . ?
C3 C4 C5 C6 -54.5(6) . . . . ?
C8 C4 C5 C6 178.9(5) . . . . ?
Se2 C4 C5 C6 62.1(5) . . . . ?
O2 S1 C9 C10 -151.1(5) . . . . ?
O3 S1 C9 C10 -21.2(6) . . . . ?
N1 S1 C9 C10 94.3(5) . . . . ?
O2 S1 C9 C14 29.1(6) . . . . ?
O3 S1 C9 C14 159.1(5) . . . . ?
N1 S1 C9 C14 -85.5(6) . . . . ?
N1 C1 C6 C5 72.0(6) . . . . ?
C2 C1 C6 C5 -49.6(6) . . . . ?
O1 C5 C6 C1 -69.4(6) . . . . ?
C4 C5 C6 C1 50.7(7) . . . . ?
C14 C9 C10 C11 0.6(10) . . . . ?
S1 C9 C10 C11 -179.2(5) . . . . ?
C10 C9 C14 C13 0.1(11) . . . . ?
S1 C9 C14 C13 179.8(6) . . . . ?
C9 C10 C11 C12 -0.8(12) . . . . ?
C10 C11 C12 C13 0.3(12) . . . . ?
C10 C11 C12 C15 179.2(7) . . . . ?
C9 C14 C13 C12 -0.6(13) . . . . ?
C11 C12 C13 C14 0.4(12) . . . . ?
C15 C12 C13 C14 -178.5(8) . . . . ?
