#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:03:00 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179437 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/34/4333438.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_4333438
loop_
_publ_author_name
'Figueroa, Joshua S.'
'Yurkerwich, Kevin'
'Melnick, Jonathan'
'Buccella, Daniela'
'Parkin, Gerard'
_publ_section_title
;
 Applications of bis(1-R-imidazol-2-yl)disulfides and diselenides as
 ligands for main-group and transition metals: kappa2-(N,N) coordination,
 S-S bond cleavage, and S-S/E-E (E = S, Se) bond metathesis reactions.
;
_journal_issue                   22
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9234
_journal_page_last               9244
_journal_paper_doi               10.1021/ic701228y
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C18 H14 N4 S2'
_chemical_formula_weight         350.45
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.9310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9142(13)
_cell_length_b                   8.8002(9)
_cell_length_c                   14.5441(15)
_cell_measurement_reflns_used    9934
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      32.96
_cell_measurement_theta_min      2.71
_cell_volume                     1652.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28112
_diffrn_reflns_theta_full        33.18
_diffrn_reflns_theta_max         33.18
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.329
_exptl_absorpt_correction_T_max  0.9523
_exptl_absorpt_correction_T_min  0.9021
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.002
_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          0.1165
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                5237
_reflns_number_total             5978
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic701228ysup1.cif
_cod_data_source_block           ky21s10
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'EMPIRICAL'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

 Adding full bibliography for 4333438--4333444.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4333438
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.356959(18) -0.46415(3) 0.540321(15) 0.01958(8) Uani 1 1 d .
S2 S 0.438014(17) -0.26473(3) 0.565545(15) 0.01860(8) Uani 1 1 d .
N12 N 0.24694(6) -0.33694(10) 0.39205(6) 0.02146(16) Uani 1 1 d .
N11 N 0.15104(7) -0.41648(12) 0.50803(7) 0.02903(19) Uani 1 1 d .
N22 N 0.30832(6) -0.07892(9) 0.65999(5) 0.01699(15) Uani 1 1 d .
N21 N 0.39947(7) -0.24111(9) 0.74921(5) 0.01979(16) Uani 1 1 d .
C11 C 0.24622(7) -0.40259(12) 0.47852(6) 0.02115(18) Uani 1 1 d .
C13 C 0.14477(8) -0.30616(14) 0.36812(8) 0.0292(2) Uani 1 1 d .
H12B H 0.1192 -0.2583 0.3134 0.035 Uiso 1 1 calc R
C12 C 0.08783(9) -0.35825(16) 0.43892(8) 0.0337(2) Uani 1 1 d .
H13A H 0.0144 -0.3547 0.4402 0.040 Uiso 1 1 calc R
C14 C 0.33596(8) -0.30423(11) 0.33940(6) 0.02007(17) Uani 1 1 d .
C15 C 0.35888(8) -0.15412(11) 0.31734(7) 0.02434(19) Uani 1 1 d .
H15A H 0.3149 -0.0738 0.3356 0.029 Uiso 1 1 calc R
C16 C 0.44722(9) -0.12369(12) 0.26813(7) 0.0270(2) Uani 1 1 d .
H16A H 0.4636 -0.0218 0.2527 0.032 Uiso 1 1 calc R
C17 C 0.51178(8) -0.24134(13) 0.24128(7) 0.0269(2) Uani 1 1 d .
H17A H 0.5719 -0.2195 0.2079 0.032 Uiso 1 1 calc R
C18 C 0.48813(8) -0.39039(13) 0.26336(7) 0.0265(2) Uani 1 1 d .
H18A H 0.5323 -0.4706 0.2453 0.032 Uiso 1 1 calc R
C19 C 0.39948(8) -0.42261(12) 0.31205(7) 0.02352(19) Uani 1 1 d .
H19A H 0.3826 -0.5247 0.3264 0.028 Uiso 1 1 calc R
C21 C 0.38133(7) -0.19281(10) 0.66351(6) 0.01696(16) Uani 1 1 d .
C23 C 0.27937(7) -0.05386(11) 0.74883(6) 0.02096(18) Uani 1 1 d .
H22B H 0.2305 0.0184 0.7691 0.025 Uiso 1 1 calc R
C22 C 0.33597(8) -0.15538(11) 0.80247(6) 0.02163(18) Uani 1 1 d .
H23A H 0.3316 -0.1647 0.8673 0.026 Uiso 1 1 calc R
C24 C 0.27061(7) 0.00383(10) 0.58040(6) 0.01704(16) Uani 1 1 d .
C25 C 0.16964(8) -0.01920(14) 0.54882(8) 0.0296(2) Uani 1 1 d .
H25A H 0.1266 -0.0907 0.5781 0.035 Uiso 1 1 calc R
C26 C 0.13182(8) 0.06407(17) 0.47329(9) 0.0359(3) Uani 1 1 d .
H26A H 0.0623 0.0499 0.4515 0.043 Uiso 1 1 calc R
C27 C 0.19494(8) 0.16747(12) 0.42973(7) 0.02426(19) Uani 1 1 d .
H27A H 0.1688 0.2245 0.3786 0.029 Uiso 1 1 calc R
C28 C 0.29622(8) 0.18653(11) 0.46153(7) 0.02271(18) Uani 1 1 d .
H28A H 0.3399 0.2562 0.4314 0.027 Uiso 1 1 calc R
C29 C 0.33495(7) 0.10465(12) 0.53733(7) 0.02278(19) Uani 1 1 d .
H29A H 0.4046 0.1181 0.5590 0.027 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'
S S 0.1246 0.1234 '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
C11 S1 S2 103.20(4)
C21 S2 S1 103.24(3)
C13 N12 C11 105.98(8)
C13 N12 C14 127.14(9)
C11 N12 C14 126.86(8)
C11 N11 C12 105.34(9)
C23 N22 C21 106.83(8)
C23 N22 C24 125.42(8)
C21 N22 C24 127.72(7)
C21 N21 C22 105.27(8)
N11 C11 N12 111.63(9)
N11 C11 S1 123.91(8)
N12 C11 S1 124.45(7)
C12 C13 N12 106.18(10)
C13 C12 N11 110.83(10)
C19 C14 C15 120.78(9)
C19 C14 N12 119.59(9)
C15 C14 N12 119.62(9)
C16 C15 C14 118.98(10)
C15 C16 C17 120.62(10)
C18 C17 C16 119.96(10)
C17 C18 C19 120.03(10)
C14 C19 C18 119.63(9)
N21 C21 N22 111.50(8)
N21 C21 S2 125.77(7)
N22 C21 S2 122.71(7)
N22 C23 C22 105.78(8)
N21 C22 C23 110.62(8)
C29 C24 C25 121.25(9)
C29 C24 N22 119.86(8)
C25 C24 N22 118.88(8)
C24 C25 C26 119.07(10)
C27 C26 C25 120.54(10)
C28 C27 C26 119.34(9)
C27 C28 C29 120.76(9)
C24 C29 C28 119.03(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C11 1.7493(10)
S1 S2 2.0699(4)
S2 C21 1.7426(9)
N12 C13 1.3801(13)
N12 C11 1.3843(12)
N12 C14 1.4318(13)
N11 C11 1.3212(12)
N11 C12 1.3725(15)
N22 C23 1.3751(12)
N22 C21 1.3757(11)
N22 C24 1.4385(11)
N21 C21 1.3303(11)
N21 C22 1.3727(12)
C13 C12 1.3647(16)
C14 C19 1.3923(13)
C14 C15 1.3936(14)
C15 C16 1.3930(15)
C16 C17 1.3934(16)
C17 C18 1.3869(16)
C18 C19 1.3954(14)
C23 C22 1.3793(13)
C24 C29 1.3803(13)
C24 C25 1.3827(13)
C25 C26 1.3950(15)
C26 C27 1.3887(15)
C27 C28 1.3828(13)
C28 C29 1.3955(13)
