#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:11:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180415 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/84/7208436.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_7208436
loop_
_publ_author_name
'Aragoni, M. Carla'
'Arca, Massimiliano'
'Caltagirone, Claudia'
'Castellano, Carlo'
'Demartin, Francesco'
'Garau, Alessandra'
'Isaia, Francesco'
'Lippolis, Vito'
'Montis, Riccardo'
'Pintus, Anna'
_publ_section_title
;
 Cationic and anionic 1D chains based on NH+⋯N charge-assisted
 hydrogen bonds in bipyridyl derivatives and polyiodides
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              5809
_journal_paper_doi               10.1039/c2ce25212k
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C12 H9 Br2 I N4 S'
_chemical_formula_weight         528.01
_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                 108.440(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.773(2)
_cell_length_b                   8.0600(10)
_cell_length_c                   18.058(3)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      3.35
_cell_volume                     1625.5(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SMART CCD diffractometer'
_diffrn_measurement_method       '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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.1707
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7647
_diffrn_reflns_theta_full        23.32
_diffrn_reflns_theta_max         23.32
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    7.009
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.523
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.841
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.841
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0285
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0252P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0640
_reflns_number_gt                1681
_reflns_number_total             2330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce25212k.txt
_cod_data_source_block           HL1IBr2
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7208436
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
I I 0.42262(4) 0.86842(5) 0.67959(2) 0.04106(15) Uani 1 1 d .
Br1 Br 0.50260(6) 0.71390(9) 0.57075(4) 0.0517(2) Uani 1 1 d .
Br2 Br 0.33860(6) 1.03356(9) 0.78114(4) 0.0484(2) Uani 1 1 d .
S S 0.66875(18) 0.6654(3) 0.98617(12) 0.0426(10) Uani 0.672(10) 1 d P
S' S 0.7119(3) 0.5578(5) 0.9313(3) 0.0619(18) Uani 0.314(11) 1 d P
N1 N 0.4904(4) 0.3301(6) 0.6680(3) 0.0365(13) Uani 1 1 d .
HN1 H 0.4231 0.3195 0.6314 0.044 Uiso 1 1 calc R
N2 N 0.7119(3) 0.5578(5) 0.9313(3) 0.0619(18) Uani 0.678(16) 1 d P
N2' N 0.66875(18) 0.6654(3) 0.98617(12) 0.0426(10) Uani 0.320(16) 1 d P
N3 N 0.4965(4) 0.5738(6) 0.8732(3) 0.0316(12) Uani 1 1 d .
N4 N 0.2256(4) 0.8161(6) 0.9385(3) 0.0394(13) Uani 1 1 d .
C1 C 0.4920(5) 0.4039(7) 0.7345(3) 0.0333(15) Uani 1 1 d .
H1 H 0.4205 0.4388 0.7410 0.040 Uiso 1 1 calc R
C2 C 0.5894(6) 0.2722(8) 0.6562(4) 0.0444(17) Uani 1 1 d .
H2 H 0.5852 0.2187 0.6097 0.053 Uiso 1 1 calc R
C3 C 0.6981(5) 0.2926(9) 0.7137(4) 0.0498(19) Uani 1 1 d .
H3 H 0.7681 0.2552 0.7057 0.060 Uiso 1 1 calc R
C4 C 0.7028(5) 0.3692(8) 0.7836(4) 0.0424(17) Uani 1 1 d .
H4 H 0.7755 0.3800 0.8232 0.051 Uiso 1 1 calc R
C5 C 0.5989(5) 0.4292(7) 0.7939(3) 0.0314(15) Uani 1 1 d .
C6 C 0.5988(5) 0.5186(7) 0.8639(3) 0.0293(15) Uani 1 1 d .
C7 C 0.5215(5) 0.6578(7) 0.9407(3) 0.0323(15) Uani 1 1 d .
C8 C 0.4313(5) 0.7363(7) 0.9669(3) 0.0298(15) Uani 1 1 d .
C9 C 0.4579(5) 0.8162(8) 1.0380(3) 0.0379(16) Uani 1 1 d .
H9 H 0.5362 0.8169 1.0717 0.045 Uiso 1 1 calc R
C10 C 0.3685(6) 0.8955(8) 1.0594(4) 0.0451(18) Uani 1 1 d .
H10 H 0.3854 0.9476 1.1077 0.054 Uiso 1 1 calc R
C11 C 0.2544(5) 0.8949(8) 1.0074(4) 0.0401(16) Uani 1 1 d .
H11 H 0.1946 0.9514 1.0205 0.048 Uiso 1 1 calc R
C12 C 0.3127(5) 0.7391(8) 0.9188(3) 0.0336(15) Uani 1 1 d .
H12 H 0.2931 0.6851 0.8709 0.040 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
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
Br2 I Br1 176.91(3)
S' S C7 99.6(3)
S S' C6 104.5(3)
C2 N1 C1 122.4(5)
C7 N3 C6 109.4(5)
C12 N4 C11 118.4(5)
N1 C1 C5 120.8(6)
N1 C2 C3 119.2(6)
C2 C3 C4 119.8(6)
C5 C4 C3 119.6(6)
C4 C5 C1 118.1(6)
C4 C5 C6 122.3(5)
C1 C5 C6 119.6(6)
N3 C6 C5 121.3(5)
N3 C6 S' 114.9(5)
C5 C6 S' 123.7(5)
N3 C7 C8 123.2(5)
N3 C7 S 111.2(5)
C8 C7 S 125.6(5)
C9 C8 C12 117.4(6)
C9 C8 C7 122.5(5)
C12 C8 C7 120.0(5)
C8 C9 C10 120.4(6)
C11 C10 C9 118.1(6)
N4 C11 C10 122.7(6)
N4 C12 C8 122.9(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I Br2 2.6946(9)
I Br1 2.7332(9)
S S' 1.520(4)
S C7 1.668(6)
S' C6 1.526(6)
N1 C2 1.334(7)
N1 C1 1.335(7)
N3 C7 1.343(7)
N3 C6 1.344(7)
N4 C12 1.338(7)
N4 C11 1.342(8)
C1 C5 1.387(8)
C2 C3 1.379(8)
C3 C4 1.392(9)
C4 C5 1.381(8)
C5 C6 1.456(8)
C7 C8 1.439(8)
C8 C9 1.380(8)
C8 C12 1.392(7)
C9 C10 1.386(8)
C10 C11 1.375(8)
