#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:45:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180447 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/16/7211672.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_7211672
loop_
_publ_author_name
'Pramanik, Avijit'
'Majumdar, Subhojit'
'Das, Gopal'
_publ_section_title
;
 Aryl azo imidazoles assisted assembly of anion/anion--water through salt
 formation
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              250
_journal_paper_doi               10.1039/b912454c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C19 H17 Br2 N9 O S'
_chemical_formula_weight         579.30
_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                 105.557(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1694(3)
_cell_length_b                   13.9841(4)
_cell_length_c                   14.3235(4)
_cell_measurement_reflns_used    3968
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.52
_cell_measurement_theta_min      2.91
_cell_volume                     2348.24(11)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_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  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20047
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    3.572
_exptl_absorpt_correction_T_max  0.377
_exptl_absorpt_correction_T_min  0.271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       reactangular
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.071
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0405P)²+0.9292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1091
_reflns_number_gt                5205
_reflns_number_total             5728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b912454c.txt
_cod_data_source_block           salt1
_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 'Multi-Scan'
changed to 'multi-scan' 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      'P2(1)/c '
_cod_database_code               7211672
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
Br2 Br -0.43461(3) 0.11756(3) 0.19733(3) 0.07071(17) Uani 1 1 d .
Br1 Br 0.67294(3) 0.85028(3) 0.04948(3) 0.07774(18) Uani 1 1 d .
S1 S 0.32951(10) 0.04511(10) 0.28006(10) 0.0924(4) Uani 1 1 d .
C16 C -0.2923(3) 0.1639(3) 0.1875(2) 0.0536(9) Uani 1 1 d .
C17 C -0.2131(4) 0.1008(3) 0.1684(3) 0.0707(11) Uani 1 1 d .
H17 H -0.2313 0.0363 0.1588 0.085 Uiso 1 1 calc R
C18 C -0.1099(4) 0.1321(4) 0.1639(3) 0.0837(14) Uani 1 1 d .
H18 H -0.0568 0.0896 0.1514 0.100 Uiso 1 1 calc R
C14 C -0.1619(4) 0.2907(3) 0.1961(3) 0.0715(12) Uani 1 1 d .
H14 H -0.1430 0.3551 0.2051 0.086 Uiso 1 1 calc R
C15 C -0.2677(3) 0.2599(3) 0.2015(2) 0.0609(10) Uani 1 1 d .
H15 H -0.3206 0.3024 0.2141 0.073 Uiso 1 1 calc R
C13 C -0.0842(3) 0.2270(5) 0.1777(3) 0.0808(15) Uani 1 1 d .
C12 C 0.3129(3) 0.4132(3) 0.1503(3) 0.0658(11) Uani 1 1 d .
H12 H 0.3557 0.4642 0.1376 0.079 Uiso 1 1 calc R
C10 C 0.1739(4) 0.3325(4) 0.1666(3) 0.0722(12) Uani 1 1 d .
C11 C 0.3536(4) 0.3262(3) 0.1765(3) 0.0755(12) Uani 1 1 d .
H11 H 0.4283 0.3054 0.1860 0.091 Uiso 1 1 calc R
N8 N 0.0488(4) 0.2422(3) 0.1767(2) 0.1124(18) Uani 1 1 d .
N7 N 0.0397(4) 0.3202(3) 0.1661(2) 0.0877(13) Uani 1 1 d .
N6 N 0.2633(4) 0.2742(3) 0.1865(2) 0.0813(11) Uani 1 1 d .
H6N H 0.2639 0.2149 0.2026 0.098 Uiso 1 1 calc R
N5 N 0.2009(3) 0.4168(3) 0.1449(2) 0.0690(9) Uani 1 1 d .
H5N H 0.1565 0.4655 0.1301 0.083 Uiso 1 1 calc R
C7 C 0.5299(3) 0.7987(3) 0.0505(3) 0.0582(10) Uani 1 1 d .
C9 C 0.3427(3) 0.8159(4) 0.0711(3) 0.0796(14) Uani 1 1 d .
H9 H 0.2855 0.8539 0.0836 0.095 Uiso 1 1 calc R
C6 C 0.5099(3) 0.7026(3) 0.0320(3) 0.0649(11) Uani 1 1 d .
H6 H 0.5659 0.6643 0.0180 0.078 Uiso 1 1 calc R
C5 C 0.4071(4) 0.6638(3) 0.0343(3) 0.0762(12) Uani 1 1 d .
H5 H 0.3939 0.5988 0.0225 0.091 Uiso 1 1 calc R
C8 C 0.4471(3) 0.8563(3) 0.0700(3) 0.0715(12) Uani 1 1 d .
H8 H 0.4605 0.9211 0.0822 0.086 Uiso 1 1 calc R
C4 C 0.3243(4) 0.7196(4) 0.0537(3) 0.0764(13) Uani 1 1 d .
C3 C -0.0621(3) 0.5543(3) 0.1111(3) 0.0623(10) Uani 1 1 d .
H3 H -0.0952 0.4983 0.1257 0.075 Uiso 1 1 calc R
C1 C 0.0572(4) 0.6548(4) 0.0793(3) 0.0693(12) Uani 1 1 d .
C2 C -0.1118(3) 0.6404(3) 0.0969(3) 0.0622(10) Uani 1 1 d .
H2 H -0.1852 0.6549 0.1003 0.075 Uiso 1 1 calc R
N4 N 0.2181(3) 0.6576(3) 0.0610(2) 0.0807(11) Uani 1 1 d .
N2 N 0.0459(2) 0.5630(3) 0.1003(2) 0.0613(8) Uani 1 1 d .
N3 N 0.1562(4) 0.7166(3) 0.0650(2) 0.0898(13) Uani 1 1 d .
N1 N -0.0364(3) 0.7023(2) 0.0769(2) 0.0670(9) Uani 1 1 d .
H1 H -0.0477 0.7623 0.0648 0.080 Uiso 1 1 calc R
C19 C 0.2216(4) 0.0183(3) 0.1911(4) 0.0710(12) Uani 1 1 d .
N9 N 0.1431(4) -0.0007(3) 0.1288(3) 0.1082(15) Uani 1 1 d .
O1 O 0.0600(4) 0.1070(2) 0.9497(4) 0.0933(11) Uani 1 1 d .
H20 H -0.005(4) 0.088(3) 0.925(3) 0.085(17) Uiso 1 1 d .
H10 H 0.079(7) 0.089(7) 1.006(7) 0.21(5) Uiso 1 1 d .
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C15 C16 C17 120.8(4)
C15 C16 Br2 119.5(3)
C17 C16 Br2 119.7(3)
C18 C17 C16 120.5(4)
C17 C18 C13 119.3(4)
C13 C14 C15 120.5(4)
C16 C15 C14 117.8(4)
C18 C13 C14 120.9(4)
C18 C13 N8 108.3(4)
C14 C13 N8 130.6(5)
C11 C12 N5 110.2(4)
N5 C10 N6 111.6(4)
N5 C10 N7 114.5(4)
N6 C10 N7 133.9(5)
C12 C11 N6 105.6(4)
N7 N8 C13 93.9(5)
N8 N7 C10 92.3(5)
C10 N6 C11 106.7(4)
C10 N5 C12 105.8(4)
C8 C7 C6 120.6(4)
C8 C7 Br1 120.4(3)
C6 C7 Br1 119.1(3)
C4 C9 C8 119.9(4)
C5 C6 C7 119.7(4)
C4 C5 C6 120.5(5)
C7 C8 C9 119.0(4)
C5 C4 C9 120.3(4)
C5 C4 N4 111.2(5)
C9 C4 N4 128.3(4)
C2 C3 N2 108.1(3)
N1 C1 N2 110.6(3)
N1 C1 N3 114.7(4)
N2 C1 N3 134.5(4)
C3 C2 N1 107.8(4)
N3 N4 C4 99.8(4)
C1 N2 C3 105.7(3)
N4 N3 C1 98.8(4)
C1 N1 C2 107.7(4)
N9 C19 S1 178.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br2 C16 1.889(4)
Br1 C7 1.888(3)
S1 C19 1.610(5)
C16 C15 1.377(5)
C16 C17 1.388(5)
C17 C18 1.348(6)
C18 C13 1.366(7)
C14 C13 1.376(6)
C14 C15 1.379(5)
C13 N8 1.635(6)
C12 C11 1.328(5)
C12 N5 1.345(4)
C10 N5 1.283(5)
C10 N6 1.327(5)
C10 N7 1.640(6)
C11 N6 1.357(5)
N8 N7 1.103(4)
C7 C8 1.375(5)
C7 C6 1.379(5)
C9 C4 1.377(6)
C9 C8 1.395(5)
C6 C5 1.372(5)
C5 C4 1.360(6)
C4 N4 1.583(6)
C3 C2 1.338(5)
C3 N2 1.369(4)
C1 N1 1.312(5)
C1 N2 1.333(5)
C1 N3 1.541(5)
C2 N1 1.346(5)
N4 N3 1.129(4)
C19 N9 1.150(5)
