#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (mar 16 de feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/26/7212624.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_7212624
loop_
_publ_author_name
'Constable, Edwin C.'
'Housecroft, Catherine E.'
'Neuburger, Markus'
'Price, Jason R.'
'Zampese, Jennifer A.'
_publ_section_title
;
 Redox addressable ligands in copper(i) coordination chemistry: thione and
 oligosulfide-bridged 6-methyl-2,2′-bipyridines
;
_journal_issue                   10
_journal_name_full               CrystEngComm
_journal_page_first              2928
_journal_paper_doi               10.1039/c002827d
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C11 H10 N2 S1'
_chemical_formula_sum            'C11 H10 N2 S'
_chemical_formula_weight         202.28
_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
_audit_creation_date             10-01-20
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                90
_cell_angle_beta                 107.011(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7126(8)
_cell_length_b                   13.4955(10)
_cell_length_c                   7.1375(6)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    173
_cell_measurement_theta_max      27
_cell_measurement_theta_min      1
_cell_volume                     986.74(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.069
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8599
_diffrn_reflns_theta_full        27.634
_diffrn_reflns_theta_max         27.634
_diffrn_reflns_theta_min         1.988
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.98
_refine_diff_density_min         -0.99
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8362
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1430
_refine_ls_R_factor_gt           0.1118
_refine_ls_shift/su_max          0.000031
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
2.90 1.50 2.11
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0992
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0899
_reflns_limit_h_max              13
_reflns_limit_h_min              0
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              -9
_reflns_number_gt                1410
_reflns_number_total             2288
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.19
_oxford_diffrn_Wilson_scale      2.60
_oxford_refine_ls_r_factor_ref   0.1071
_oxford_refine_ls_scale          0.693(6)
_oxford_reflns_number_all        2275
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_oxford_structure_analysis_title '4171010 jp5_173k'
_cod_data_source_file            c002827d.txt
_cod_data_source_block           jp5
_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.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C11 H10 N2 S1'
_cod_database_code               7212624
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
S1 S -0.19584(14) 0.04958(10) 0.3413(2) 0.0487 1.0000 Uani .
N1 N 0.0112(4) 0.1558(3) 0.3319(6) 0.0362 1.0000 Uani .
N2 N 0.2486(4) 0.1226(3) 0.2942(6) 0.0364 1.0000 Uani .
C1 C -0.1155(5) 0.1565(4) 0.3330(8) 0.0389 1.0000 Uani .
C2 C -0.1701(5) 0.2533(4) 0.3299(8) 0.0412 1.0000 Uani .
C3 C -0.0980(5) 0.3354(4) 0.3236(8) 0.0433 1.0000 Uani .
C4 C 0.0318(5) 0.3289(4) 0.3195(7) 0.0391 1.0000 Uani .
C5 C 0.0858(5) 0.2369(4) 0.3239(7) 0.0356 1.0000 Uani .
C6 C 0.2208(5) 0.2176(4) 0.3213(7) 0.0343 1.0000 Uani .
C7 C 0.3122(5) 0.2932(4) 0.3465(8) 0.0395 1.0000 Uani .
C8 C 0.4385(5) 0.2689(4) 0.3548(8) 0.0430 1.0000 Uani .
C9 C 0.4686(5) 0.1707(4) 0.3288(8) 0.0425 1.0000 Uani .
C10 C 0.3700(5) 0.0996(4) 0.2955(8) 0.0375 1.0000 Uani .
C11 C 0.3964(5) -0.0061(4) 0.2534(9) 0.0474 1.0000 Uani .
H21 H -0.2557 0.2615 0.3322 0.0496 1.0000 Uiso R
H31 H -0.1343 0.3987 0.3227 0.0526 1.0000 Uiso R
H41 H 0.0789 0.3858 0.3125 0.0469 1.0000 Uiso R
H71 H 0.2893 0.3585 0.3588 0.0482 1.0000 Uiso R
H81 H 0.5030 0.3170 0.3790 0.0507 1.0000 Uiso R
H91 H 0.5521 0.1522 0.3332 0.0519 1.0000 Uiso R
H112 H 0.4885 -0.0140 0.2768 0.0700 1.0000 Uiso R
H113 H 0.3672 -0.0484 0.3400 0.0697 1.0000 Uiso R
H111 H 0.3519 -0.0221 0.1200 0.0697 1.0000 Uiso R
H11 H 0.0491 0.0982 0.3372 0.0432 1.0000 Uiso 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
S1 0.0421(7) 0.0373(7) 0.0695(11) -0.0082(8) 0.0206(7) -0.0042(7)
N1 0.038(2) 0.034(2) 0.037(2) 0.0004(19) 0.0112(19) 0.0029(18)
N2 0.043(2) 0.029(2) 0.037(2) 0.0045(19) 0.0108(19) -0.0006(18)
C1 0.036(3) 0.031(2) 0.050(3) -0.003(2) 0.014(2) 0.000(2)
C2 0.042(3) 0.038(3) 0.046(3) 0.003(2) 0.016(2) 0.002(2)
C3 0.048(3) 0.039(3) 0.045(3) 0.004(3) 0.016(3) 0.011(2)
C4 0.047(3) 0.037(3) 0.035(3) 0.007(2) 0.014(2) 0.005(2)
C5 0.045(3) 0.032(2) 0.031(3) 0.001(2) 0.012(2) -0.001(2)
C6 0.040(3) 0.032(2) 0.032(3) 0.006(2) 0.012(2) 0.003(2)
C7 0.047(3) 0.032(2) 0.040(3) 0.005(2) 0.014(2) -0.001(2)
C8 0.041(3) 0.035(3) 0.051(3) 0.004(2) 0.010(2) -0.008(2)
C9 0.032(2) 0.046(3) 0.051(3) 0.004(3) 0.014(2) 0.003(2)
C10 0.038(3) 0.037(3) 0.036(3) 0.004(2) 0.010(2) 0.003(2)
C11 0.038(3) 0.041(3) 0.061(4) -0.006(3) 0.011(3) 0.002(2)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 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 N1 C5 126.2(4) yes
C1 N1 H11 117.3 no
C5 N1 H11 116.4 no
C6 N2 C10 118.6(4) yes
N1 C1 S1 120.9(4) yes
N1 C1 C2 114.3(4) yes
S1 C1 C2 124.8(4) yes
C1 C2 C3 120.8(5) yes
C1 C2 H21 120.7 no
C3 C2 H21 118.5 no
C2 C3 C4 121.8(5) yes
C2 C3 H31 120.3 no
C4 C3 H31 117.9 no
C3 C4 C5 118.2(5) yes
C3 C4 H41 120.5 no
C5 C4 H41 121.3 no
N1 C5 C4 118.7(4) yes
N1 C5 C6 116.5(4) yes
C4 C5 C6 124.8(4) yes
C5 C6 N2 115.5(4) yes
C5 C6 C7 121.7(5) yes
N2 C6 C7 122.8(4) yes
C6 C7 C8 118.5(5) yes
C6 C7 H71 121.0 no
C8 C7 H71 120.5 no
C7 C8 C9 119.0(5) yes
C7 C8 H81 120.8 no
C9 C8 H81 120.2 no
C8 C9 C10 119.1(5) yes
C8 C9 H91 121.0 no
C10 C9 H91 119.9 no
C9 C10 N2 121.9(5) yes
C9 C10 C11 120.7(5) yes
N2 C10 C11 117.4(4) yes
C10 C11 H112 108.4 no
C10 C11 H113 108.6 no
H112 C11 H113 109.7 no
C10 C11 H111 110.2 no
H112 C11 H111 109.7 no
H113 C11 H111 110.2 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.690(5) yes
N1 C1 1.360(6) yes
N1 C5 1.367(6) yes
N1 H11 0.872 no
N2 C6 1.342(6) yes
N2 C10 1.334(7) yes
C1 C2 1.428(7) yes
C2 C3 1.358(8) yes
C2 H21 0.930 no
C3 C4 1.402(7) yes
C3 H31 0.938 no
C4 C5 1.365(7) yes
C4 H41 0.929 no
C5 C6 1.475(7) yes
C6 C7 1.389(7) yes
C7 C8 1.376(7) yes
C7 H71 0.927 no
C8 C9 1.389(7) yes
C8 H81 0.927 no
C9 C10 1.395(7) yes
C9 H91 0.921 no
C10 C11 1.501(7) yes
C11 H112 0.957 no
C11 H113 0.959 no
C11 H111 0.957 no
loop_
_oxford_twin_element_scale_factors
0.763(11)
0.432(11)
