#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/12/7101210.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_7101210
loop_
_publ_author_name
'Paul Ragogna'
'Jason L. Dutton'
'Michael C. Jennings'
'Jocelyn J. Tindale'
_publ_section_title
;
The Direct Reaction of the tBu-DAB Ligand with SeCl4:
A Redox Route to Selenium-Nitrogen Heterocycles
;
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/b603777a
_journal_year                    2006
_chemical_formula_sum            'C6 H11 Cl N2 Se'
_chemical_formula_weight         225.58
_chemical_name_systematic
;
?
;
_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                 104.012(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1855(7)
_cell_length_b                   9.2467(7)
_cell_length_c                   10.3396(6)
_cell_measurement_reflns_used    2553
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      1.70
_cell_volume                     852.07(10)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001)'
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2001)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'φ scans, and ω scans with κ offsets'
_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  0.060
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10131
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.649
_exptl_absorpt_correction_T_max  0.6054
_exptl_absorpt_correction_T_min  0.4210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         .462
_refine_diff_density_min         -.631
_refine_diff_density_rms         .108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0326
_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)+(0.0347P)²+0.0079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0738
_reflns_number_gt                1669
_reflns_number_total             2110
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b603777a.txt
_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.

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               7101210
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
Se1 Se 0.01109(3) 0.03708(3) 0.27627(3) 0.02001(10) Uani 1 1 d .
Cl1 Cl -0.21503(8) -0.00519(8) 0.38277(7) 0.02454(17) Uani 1 1 d .
N1 N -0.1177(3) 0.1280(3) 0.1408(2) 0.0219(5) Uani 1 1 d .
C1 C -0.0495(3) 0.1800(3) 0.0542(2) 0.0229(6) Uani 1 1 d .
H2A H -0.1035 0.2321 -0.0215 0.027 Uiso 1 1 calc R
C2 C 0.1072(3) 0.1571(3) 0.0754(2) 0.0210(6) Uani 1 1 d .
H3A H 0.1641 0.1914 0.0163 0.025 Uiso 1 1 calc R
N2 N 0.1653(2) 0.0849(3) 0.1830(2) 0.0183(5) Uani 1 1 d .
C5 C 0.3295(3) 0.0530(3) 0.2372(3) 0.0196(6) Uani 1 1 d .
C6 C 0.3887(3) 0.1671(3) 0.3430(2) 0.0252(7) Uani 1 1 d .
H6A H 0.3351 0.1598 0.4140 0.038 Uiso 1 1 calc R
H6B H 0.3729 0.2635 0.3026 0.038 Uiso 1 1 calc R
H6C H 0.4962 0.1516 0.3806 0.038 Uiso 1 1 calc R
C7 C 0.4110(3) 0.0604(3) 0.1255(3) 0.0257(7) Uani 1 1 d .
H7A H 0.3710 -0.0139 0.0588 0.038 Uiso 1 1 calc R
H7B H 0.5184 0.0437 0.1622 0.038 Uiso 1 1 calc R
H7C H 0.3960 0.1561 0.0837 0.038 Uiso 1 1 calc R
C8 C 0.3442(3) -0.0971(3) 0.2995(3) 0.0241(6) Uani 1 1 d .
H8A H 0.3060 -0.1693 0.2302 0.036 Uiso 1 1 calc R
H8B H 0.2862 -0.1015 0.3673 0.036 Uiso 1 1 calc R
H8C H 0.4501 -0.1170 0.3409 0.036 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Se1 0.01736(16) 0.02342(18) 0.01958(16) 0.00156(11) 0.00512(11) 0.00178(12)
Cl1 0.0194(4) 0.0297(4) 0.0258(4) -0.0005(3) 0.0079(3) -0.0012(3)
N1 0.0224(13) 0.0212(14) 0.0212(11) -0.0025(10) 0.0034(10) 0.0023(10)
C1 0.0258(16) 0.0206(16) 0.0201(14) 0.0009(12) 0.0013(12) 0.0037(13)
C2 0.0265(16) 0.0186(15) 0.0182(13) -0.0005(11) 0.0058(12) -0.0009(13)
N2 0.0182(12) 0.0192(13) 0.0179(11) -0.0005(10) 0.0053(9) 0.0005(10)
C5 0.0151(14) 0.0244(17) 0.0202(14) -0.0002(11) 0.0062(11) 0.0013(12)
C6 0.0218(16) 0.0304(18) 0.0238(14) -0.0015(13) 0.0065(12) -0.0028(13)
C7 0.0212(16) 0.036(2) 0.0210(14) 0.0004(12) 0.0080(12) 0.0005(13)
C8 0.0211(15) 0.0258(17) 0.0261(15) 0.0015(13) 0.0072(12) 0.0022(13)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -.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
N1 Se1 N2 85.91(10)
N1 Se1 Cl1 87.60(8)
N2 Se1 Cl1 173.31(7)
C1 N1 Se1 111.8(2)
N1 C1 C2 118.5(2)
N1 C1 H2A 120.7
C2 C1 H2A 120.7
N2 C2 C1 113.7(2)
N2 C2 H3A 123.2
C1 C2 H3A 123.2
C2 N2 C5 126.0(2)
C2 N2 Se1 110.10(19)
C5 N2 Se1 123.64(16)
N2 C5 C8 108.4(2)
N2 C5 C7 109.9(2)
C8 C5 C7 110.6(2)
N2 C5 C6 106.4(2)
C8 C5 C6 110.4(2)
C7 C5 C6 111.0(2)
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Se1 N1 1.807(2)
Se1 N2 1.948(2)
Se1 Cl1 2.6051(8)
N1 C1 1.303(3)
C1 C2 1.418(4)
C1 H2A 0.9500
C2 N2 1.297(3)
C2 H3A 0.9500
N2 C5 1.505(3)
C5 C8 1.522(4)
C5 C7 1.522(4)
C5 C6 1.523(4)
C6 H6A 0.9800
C6 H6B 0.9800
C6 H6C 0.9800
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
N2 Se1 N1 C1 -1.1(2)
Cl1 Se1 N1 C1 177.23(19)
Se1 N1 C1 C2 1.1(3)
N1 C1 C2 N2 -0.3(4)
C1 C2 N2 C5 -175.3(2)
C1 C2 N2 Se1 -0.6(3)
N1 Se1 N2 C2 1.00(19)
Cl1 Se1 N2 C2 -13.1(7)
N1 Se1 N2 C5 175.9(2)
Cl1 Se1 N2 C5 161.8(5)
C2 N2 C5 C8 -144.3(3)
Se1 N2 C5 C8 41.7(3)
C2 N2 C5 C7 -23.3(4)
Se1 N2 C5 C7 162.70(19)
C2 N2 C5 C6 97.0(3)
Se1 N2 C5 C6 -77.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652979
