#------------------------------------------------------------------------------
#$Date: 2019-06-20 16:09:56 +0300 (Thu, 20 Jun 2019) $
#$Revision: 216392 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/17/1551780.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_1551780
loop_
_publ_author_name
'YAN, Zhen-Zhong'
'HOU, Na'
'LIANG, Hua-Ding'
'ZHAO, Song-Lin'
'TANG, Yu'
_publ_section_title
;
 Synthesis and Crystal Structure of
 1,1′-Butane-1,4-diyl-dibenzimidazolium Picrate
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              31
_journal_paper_doi               10.2116/xraystruct.25.31
_journal_volume                  25
_journal_year                    2009
_chemical_formula_sum            'C32 H32 N10 O16'
_chemical_formula_weight         812.68
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.000(4)
_cell_angle_beta                 104.942(3)
_cell_angle_gamma                94.865(4)
_cell_formula_units_Z            1
_cell_length_a                   6.9285(6)
_cell_length_b                   10.8287(9)
_cell_length_c                   12.9941(11)
_cell_measurement_reflns_used    none
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      0.9760
_cell_measurement_theta_min      0.9580
_cell_volume                     918.99(14)
_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      294(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0138
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4870
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0640
_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)+(0.1019P)²+0.3880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1932
_reflns_number_gt                2375
_reflns_number_total             3334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            25_31_1.cif
_cod_data_source_block           p-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/andrius/struct/COD-crude-data/automatic-downloads/current/J-STAGE/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 6524 2018-11-02 12:15:13Z antanas 
;
_cod_original_cell_volume        918.99(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1551780
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C3 C 0.2381(4) 0.8890(3) 0.5014(2) 0.0452(6) Uani 1 1 d . A 4
C5 C 0.2566(4) 1.0175(2) 0.48428(19) 0.0408(6) Uani 1 1 d . A 4
C6 C 0.2583(4) 1.1225(3) 0.5620(2) 0.0449(6) Uani 1 1 d . A 4
H6 H 0.2699 1.2031 0.5466 0.054 Uiso 1 1 calc R A 4
C9 C 0.2426(4) 1.1066(3) 0.6628(2) 0.0467(6) Uani 1 1 d . A 4
C10 C 0.2610(4) 0.5278(3) 0.0913(2) 0.0448(6) Uani 1 1 d . B 4
C11 C 0.2195(4) 0.8847(3) 0.6097(2) 0.0475(6) Uani 1 1 d . A 4
C13 C 0.2234(4) 0.9872(3) 0.6865(2) 0.0507(7) Uani 1 1 d . A 4
H13 H 0.2133 0.9776 0.7548 0.061 Uiso 1 1 calc R A 4
C15 C 0.2699(4) 0.5288(3) 0.2635(2) 0.0468(6) Uani 1 1 d . B 4
C16 C 0.2422(4) 0.6486(3) 0.1402(2) 0.0449(6) Uani 1 1 d . B 4
C19 C 0.2356(5) 0.5922(3) -0.0744(2) 0.0581(8) Uani 1 1 d . B 4
H19 H 0.2335 0.5753 -0.1473 0.070 Uiso 1 1 calc R B 4
C21 C 0.4911(5) 0.5274(3) 0.4491(2) 0.0525(7) Uani 1 1 d . . 4
H21A H 0.5144 0.6190 0.4694 0.063 Uiso 1 1 calc R . 4
H21B H 0.5942 0.5002 0.4154 0.063 Uiso 1 1 calc R . 4
C22 C 0.2575(4) 0.4974(3) -0.0175(2) 0.0541(7) Uani 1 1 d . B 4
H22 H 0.2695 0.4160 -0.0501 0.065 Uiso 1 1 calc R B 4
C23 C 0.2853(5) 0.4858(3) 0.3676(2) 0.0552(7) Uani 1 1 d . B 4
H23A H 0.2573 0.3942 0.3526 0.066 Uiso 1 1 calc R B 4
H23B H 0.1836 0.5192 0.3995 0.066 Uiso 1 1 calc R B 4
C24 C 0.2181(5) 0.7449(3) 0.0819(2) 0.0607(8) Uani 1 1 d . B 4
H24 H 0.2040 0.8262 0.1139 0.073 Uiso 1 1 calc R B 4
C26 C 0.2162(5) 0.7139(3) -0.0257(2) 0.0641(8) Uani 1 1 d . B 4
H26 H 0.2015 0.7762 -0.0672 0.077 Uiso 1 1 calc R B 4
C30 C 0.2990(10) 0.1098(5) 0.0747(4) 0.1180(18) Uani 1 1 d . . .
H30A H 0.3453 0.1521 0.0246 0.177 Uiso 1 1 calc R . .
H30B H 0.1759 0.0547 0.0367 0.177 Uiso 1 1 calc R . .
H30C H 0.3994 0.0611 0.1063 0.177 Uiso 1 1 calc R . .
H1 H 0.240(5) 0.712(3) 0.299(3) 0.059(9) Uiso 1 1 d . . .
H2N H 0.292(5) 0.369(3) 0.165(3) 0.065(9) Uiso 1 1 d . . .
N1 N 0.2483(4) 0.6452(2) 0.24741(18) 0.0488(6) Uani 1 1 d . B 4
N2 N 0.2790(4) 0.4560(2) 0.17123(18) 0.0493(6) Uani 1 1 d . B 4
N3 N 0.1896(5) 0.7614(3) 0.6374(3) 0.0752(9) Uani 1 1 d . A 4
N4 N 0.2388(4) 1.2173(3) 0.7433(2) 0.0629(7) Uani 1 1 d . A 4
N5 N 0.2691(3) 1.0415(2) 0.37995(18) 0.0496(6) Uani 1 1 d . A 4
O1 O 0.2617(4) 0.9539(2) 0.30585(17) 0.0804(8) Uani 1 1 d . A 4
O2 O 0.2889(5) 1.1507(2) 0.3685(2) 0.0852(8) Uani 1 1 d . A 4
O3 O 0.0742(8) 0.6736(4) 0.5598(4) 0.0559(10) Uani 0.50 1 d P . .
O4 O 0.2419(4) 0.79291(19) 0.43519(17) 0.0675(6) Uani 1 1 d . A 4
O5 O 0.2824(11) 0.7447(5) 0.7231(4) 0.0962(19) Uani 0.50 1 d P . .
O6 O 0.2133(5) 1.1988(3) 0.8297(2) 0.0988(10) Uani 1 1 d . A 4
O7 O 0.2612(4) 1.3220(2) 0.7226(2) 0.0834(8) Uani 1 1 d . A 4
O8 O 0.2657(7) 0.1964(3) 0.1539(2) 0.1187(12) Uani 1 1 d . . .
H8 H 0.2649 0.1645 0.2066 0.178 Uiso 1 1 calc R . .
O3' O 0.192(2) 0.6731(15) 0.5954(12) 0.201(6) Uiso 0.50 1 d P A .
O5' O 0.1309(15) 0.7567(9) 0.7217(8) 0.135(3) Uiso 0.50 1 d P A .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O4 C3 C5 125.8(2) . .
O4 C3 C11 122.6(3) . .
C5 C3 C11 111.6(2) . .
C6 C5 N5 116.1(2) . .
C6 C5 C3 123.8(2) . .
N5 C5 C3 120.1(2) . .
C9 C6 C5 119.3(2) . .
C9 C6 H6 120.3 . .
C5 C6 H6 120.3 . .
C6 C9 C13 121.0(2) . .
C6 C9 N4 119.0(3) . .
C13 C9 N4 119.9(2) . .
C16 C10 N2 106.1(2) . .
C16 C10 C22 121.8(3) . .
N2 C10 C22 132.2(3) . .
C13 C11 C3 124.9(3) . .
C13 C11 N3 117.0(3) . .
C3 C11 N3 118.1(3) . .
C11 C13 C9 119.4(2) . .
C11 C13 H13 120.3 . .
C9 C13 H13 120.3 . .
N1 C15 N2 109.0(2) . .
N1 C15 C23 125.9(2) . .
N2 C15 C23 125.1(2) . .
C10 C16 C24 121.2(2) . .
C10 C16 N1 106.7(2) . .
C24 C16 N1 132.1(3) . .
C22 C19 C26 121.5(3) . .
C22 C19 H19 119.3 . .
C26 C19 H19 119.3 . .
C23 C21 C21 111.9(3) . 2_666
C23 C21 H21A 109.2 . .
C21 C21 H21A 109.2 2_666 .
C23 C21 H21B 109.2 . .
C21 C21 H21B 109.2 2_666 .
H21A C21 H21B 107.9 . .
C19 C22 C10 117.0(3) . .
C19 C22 H22 121.5 . .
C10 C22 H22 121.5 . .
C15 C23 C21 113.0(2) . .
C15 C23 H23A 109.0 . .
C21 C23 H23A 109.0 . .
C15 C23 H23B 109.0 . .
C21 C23 H23B 109.0 . .
H23A C23 H23B 107.8 . .
C26 C24 C16 116.5(3) . .
C26 C24 H24 121.7 . .
C16 C24 H24 121.7 . .
C24 C26 C19 122.0(3) . .
C24 C26 H26 119.0 . .
C19 C26 H26 119.0 . .
O8 C30 H30A 109.5 . .
O8 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
O8 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C15 N1 C16 109.0(2) . .
C15 N1 H1 125(2) . .
C16 N1 H1 126(2) . .
C15 N2 C10 109.3(2) . .
C15 N2 H2N 122(2) . .
C10 N2 H2N 128.3(19) . .
O3' N3 O5 95.6(9) . .
O3' N3 O5' 111.5(10) . .
O5 N3 O5' 51.3(4) . .
O3' N3 O3 39.7(9) . .
O5 N3 O3 124.8(4) . .
O5' N3 O3 106.8(5) . .
O3' N3 C11 130.6(9) . .
O5 N3 C11 119.4(4) . .
O5' N3 C11 117.5(5) . .
O3 N3 C11 115.4(3) . .
O7 N4 O6 123.5(3) . .
O7 N4 C9 119.3(3) . .
O6 N4 C9 117.1(3) . .
O1 N5 O2 121.1(2) . .
O1 N5 C5 120.3(2) . .
O2 N5 C5 118.6(2) . .
O3' O3 N3 51.8(12) . .
O5' O5 N3 68.5(6) . .
O5' O5 O3' 86.4(8) . .
N3 O5 O3' 38.3(5) . .
C30 O8 H8 109.5 . .
O3 O3' N3 88.6(15) . .
O3 O3' O5 122.9(16) . .
N3 O3' O5 46.1(7) . .
O5 O5' N3 60.3(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C3 O4 1.237(3) .
C3 C5 1.448(4) .
C3 C11 1.453(4) .
C5 C6 1.380(4) .
C5 N5 1.446(3) .
C6 C9 1.380(4) .
C6 H6 0.9300 .
C9 C13 1.384(4) .
C9 N4 1.454(4) .
C10 C16 1.384(4) .
C10 N2 1.388(3) .
C10 C22 1.388(4) .
C11 C13 1.351(4) .
C11 N3 1.455(4) .
C13 H13 0.9300 .
C15 N1 1.328(4) .
C15 N2 1.335(3) .
C15 C23 1.486(4) .
C16 C24 1.389(4) .
C16 N1 1.390(3) .
C19 C22 1.362(4) .
C19 C26 1.392(5) .
C19 H19 0.9300 .
C21 C23 1.518(4) .
C21 C21 1.522(5) 2_666
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C22 H22 0.9300 .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 C26 1.377(4) .
C24 H24 0.9300 .
C26 H26 0.9300 .
C30 O8 1.347(5) .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
N1 H1 0.92(3) .
N2 H2N 0.95(4) .
N3 O3' 1.019(15) .
N3 O5 1.185(5) .
N3 O5' 1.269(9) .
N3 O3 1.297(6) .
N4 O7 1.216(4) .
N4 O6 1.228(4) .
N5 O1 1.216(3) .
N5 O2 1.218(3) .
O3 O3' 0.828(14) .
O5 O5' 1.065(9) .
O5 O3' 1.637(16) .
O8 H8 0.8200 .
