#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:20:51 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178946 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/75/4117576.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_4117576
loop_
_publ_author_name
'Debasish Manna'
'Govindasamy Mugesh'
_publ_section_title
;
 Regioselective Deiodination of Thyroxine by Iodothyronine Deiodinase
 Mimics: An Unusual Mechanistic Pathway Involving Cooperative Chalcogen
 and Halogen Bonding
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4269
_journal_page_last               4279
_journal_paper_doi               10.1021/ja210478k
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C14 H13 N Se2'
_chemical_formula_sum            'C14 H13 N Se2'
_chemical_formula_weight         353.17
_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                 93.079(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8085(11)
_cell_length_b                   11.5763(11)
_cell_length_c                   10.5415(10)
_cell_measurement_temperature    296(2)
_cell_volume                     1317.1(2)
_computing_cell_refinement       'Bruker kappa apex ccd'
_computing_data_collection       'Bruker kappa apex ccd'
_computing_data_reduction        'Bruker saint'
_computing_molecular_graphics    ortep-III
_computing_publication_material  WinGX1.80.05
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0.3
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6053
_diffrn_reflns_theta_full        26.78
_diffrn_reflns_theta_max         26.78
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    5.591
_exptl_absorpt_correction_T_max  0.9058
_exptl_absorpt_correction_T_min  0.7629
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_description       'needle shape'
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.806
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0406
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1395
_reflns_number_gt                1644
_reflns_number_total             2665
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ja210478k_si_003.cif
_cod_data_source_block           dm120
_cod_original_sg_symbol_H-M      'P -1'
_cod_database_code               4117576
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 0.78654(6) -0.04127(6) 0.29603(5) 0.0612(2) Uani 1 1 d .
Se2 Se 0.70419(5) 0.05947(5) 0.10289(5) 0.0508(2) Uani 1 1 d .
N1 N 0.6743(4) 0.1629(4) -0.0811(4) 0.0516(11) Uani 1 1 d .
C1 C 0.9510(5) 0.0060(4) 0.2680(4) 0.0434(12) Uani 1 1 d .
C2 C 1.0498(6) -0.0260(5) 0.3439(5) 0.0531(14) Uani 1 1 d .
H2 H 1.0387 -0.0750 0.4122 0.064 Uiso 1 1 calc R
C3 C 1.1689(6) 0.0141(5) 0.3204(5) 0.0601(15) Uani 1 1 d .
H3 H 1.2355 -0.0071 0.3749 0.072 Uiso 1 1 calc R
C4 C 1.1885(5) 0.0837(5) 0.2190(5) 0.0525(14) Uani 1 1 d .
H4 H 1.2681 0.1095 0.2050 0.063 Uiso 1 1 calc R
C5 C 1.0888(5) 0.1166(4) 0.1357(5) 0.0404(11) Uani 1 1 d .
C6 C 1.1035(5) 0.1866(4) 0.0255(5) 0.0470(13) Uani 1 1 d .
H6 H 1.1821 0.2130 0.0083 0.056 Uiso 1 1 calc R
C7 C 1.0068(5) 0.2152(4) -0.0538(5) 0.0477(13) Uani 1 1 d .
H7 H 1.0198 0.2605 -0.1246 0.057 Uiso 1 1 calc R
C8 C 0.8856(5) 0.1773(4) -0.0311(4) 0.0406(12) Uani 1 1 d .
C9 C 0.8672(4) 0.1102(4) 0.0760(4) 0.0331(10) Uani 1 1 d .
C10 C 0.9667(5) 0.0772(4) 0.1597(4) 0.0368(11) Uani 1 1 d .
C11 C 0.7784(5) 0.2014(4) -0.1124(5) 0.0493(14) Uani 1 1 d .
H11 H 0.7849 0.2442 -0.1864 0.059 Uiso 1 1 calc R
C12 C 0.5596(6) 0.1791(6) -0.1609(6) 0.0761(19) Uani 1 1 d .
H12A H 0.5288 0.1047 -0.1908 0.091 Uiso 1 1 calc R
H12B H 0.5766 0.2259 -0.2342 0.091 Uiso 1 1 calc R
C13 C 0.4606(6) 0.2393(8) -0.0830(8) 0.097(3) Uani 1 1 d .
H13A H 0.3829 0.2407 -0.1335 0.117 Uiso 1 1 calc R
H13B H 0.4480 0.1936 -0.0077 0.117 Uiso 1 1 calc R
C14 C 0.4907(7) 0.3536(8) -0.0451(10) 0.121(3) Uani 1 1 d .
H14A H 0.5583 0.3521 0.0179 0.182 Uiso 1 1 calc R
H14B H 0.4200 0.3891 -0.0100 0.182 Uiso 1 1 calc R
H14C H 0.5144 0.3971 -0.1174 0.182 Uiso 1 1 calc 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'
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
C1 Se1 Se2 91.97(15)
C9 Se2 N1 78.50(18)
C9 Se2 Se1 88.45(14)
N1 Se2 Se1 166.93(13)
C11 N1 C12 122.5(5)
C11 N1 Se2 108.5(3)
C12 N1 Se2 128.8(4)
C2 C1 C10 120.5(5)
C2 C1 Se1 123.1(4)
C10 C1 Se1 116.4(4)
C1 C2 C3 120.6(5)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 121.1(5)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 120.2(5)
C3 C4 H4 119.9
C5 C4 H4 119.9
C4 C5 C10 119.1(5)
C4 C5 C6 123.1(5)
C10 C5 C6 117.8(5)
C7 C6 C5 121.8(5)
C7 C6 H6 119.1
C5 C6 H6 119.1
C6 C7 C8 121.0(5)
C6 C7 H7 119.5
C8 C7 H7 119.5
C9 C8 C7 118.9(5)
C9 C8 C11 116.6(5)
C7 C8 C11 124.4(4)
C8 C9 C10 121.4(4)
C8 C9 Se2 118.0(4)
C10 C9 Se2 120.5(3)
C9 C10 C1 122.6(5)
C9 C10 C5 119.0(4)
C1 C10 C5 118.4(5)
N1 C11 C8 118.4(5)
N1 C11 H11 120.8
C8 C11 H11 120.8
N1 C12 C13 109.8(5)
N1 C12 H12A 109.7
C13 C12 H12A 109.7
N1 C12 H12B 109.7
C13 C12 H12B 109.7
H12A C12 H12B 108.2
C14 C13 C12 114.5(6)
C14 C13 H13A 108.6
C12 C13 H13A 108.6
C14 C13 H13B 108.6
C12 C13 H13B 108.6
H13A C13 H13B 107.6
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
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
Se1 C1 1.898(5)
Se1 Se2 2.4704(8)
Se2 C9 1.893(4)
Se2 N1 2.287(4)
N1 C11 1.270(6)
N1 C12 1.472(7)
C1 C2 1.351(7)
C1 C10 1.426(6)
C2 C3 1.402(8)
C2 H2 0.9300
C3 C4 1.364(8)
C3 H3 0.9300
C4 C5 1.405(7)
C4 H4 0.9300
C5 C10 1.432(7)
C5 C6 1.432(7)
C6 C7 1.344(7)
C6 H6 0.9300
C7 C8 1.414(7)
C7 H7 0.9300
C8 C9 1.393(6)
C8 C11 1.431(7)
C9 C10 1.407(6)
C11 H11 0.9300
C12 C13 1.549(9)
C12 H12A 0.9700
C12 H12B 0.9700
C13 C14 1.415(10)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
