#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:07:59 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180376 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/45/7204584.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_7204584
loop_
_publ_author_name
'Dudd, Lucinda M.'
'Venardou, Eleni'
'Garcia-Verdugo, Eduardo'
'Licence, Peter'
'Blake, Alexander J.'
'Wilson, Claire'
'Poliakoff, Martyn'
_publ_section_title
;
 Synthesis of benzimidazoles in high-temperature waterThis work was
 presented at the Green Solvents for Catalysis Meeting held in
 Bruchsal, Germany, 13--16th October 2002.Electronic supplementary
 information (ESI) available: analytical data for compounds 3a--f and
 5g--j. See http://www.rsc.org/suppdata/gc/b2/b212394k/
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              187
_journal_paper_doi               10.1039/b212394k
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         'C16 H14 N4'
_chemical_formula_sum            'C16 H14 N4'
_chemical_formula_weight         262.31
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   'geometrically placed, NH located deltaF'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5187(9)
_cell_length_b                   9.8623(11)
_cell_length_c                   14.8684(15)
_cell_measurement_reflns_used    1524
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.8
_cell_measurement_theta_min      3.45
_cell_volume                     1249.2(2)
_computing_cell_refinement       'Bruker SAINT version 6.02a (Bruker, 2000)'
_computing_data_collection       'Bruker SMART version 5.054 (Bruker, 1998)'
_computing_data_reduction        'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97; PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_av_sigmaI/netI    0.0391
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5853
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.85
_diffrn_reflns_theta_min         2.74
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'plate cut from large block'
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0431P)²+0.2665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0999
_reflns_number_gt                1012
_reflns_number_total             1712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b212394k.txt
_cod_data_source_block           imphpr
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7204584
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
N1 N 0.24009(14) 0.61669(11) 0.06126(8) 0.0198(3) Uani 1 1 d . . .
C2 C 0.28298(16) 0.49449(14) 0.03383(10) 0.0186(3) Uani 1 1 d . . .
N3 N 0.18177(13) 0.39548(12) 0.05999(8) 0.0190(3) Uani 1 1 d . . .
H3 H 0.1897 0.3084 0.0479 0.023 Uiso 1 1 calc R . .
C3A C 0.06395(16) 0.45740(14) 0.10915(10) 0.0182(3) Uani 1 1 d . . .
C4 C -0.06586(17) 0.40569(16) 0.15456(10) 0.0230(4) Uani 1 1 d . . .
H4 H -0.0912 0.3119 0.1528 0.028 Uiso 1 1 calc R . .
C5 C -0.15626(17) 0.49749(16) 0.20239(10) 0.0255(4) Uani 1 1 d . . .
H5 H -0.2454 0.4662 0.2347 0.031 Uiso 1 1 calc R . .
C6 C -0.11835(18) 0.63634(16) 0.20397(10) 0.0255(4) Uani 1 1 d . . .
H6 H -0.1822 0.6966 0.2378 0.031 Uiso 1 1 calc R . .
C7A C 0.10180(16) 0.59575(14) 0.10962(10) 0.0184(3) Uani 1 1 d . . .
C7 C 0.00905(17) 0.68728(15) 0.15767(11) 0.0231(4) Uani 1 1 d . . .
H7 H 0.0328 0.7814 0.1585 0.028 Uiso 1 1 calc R . .
C8 C 0.42779(16) 0.46338(15) -0.01873(11) 0.0217(4) Uani 1 1 d . . .
H8B H 0.4118 0.4907 -0.0821 0.026 Uiso 1 1 calc R . .
H8A H 0.4467 0.3643 -0.0176 0.026 Uiso 1 1 calc 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
N1 0.0188(6) 0.0175(6) 0.0230(7) -0.0019(5) 0.0012(5) 0.0007(5)
C2 0.0169(7) 0.0184(7) 0.0206(8) -0.0011(6) -0.0037(6) -0.0008(5)
N3 0.0174(6) 0.0146(6) 0.0249(7) -0.0022(5) 0.0004(5) 0.0003(4)
C3A 0.0171(7) 0.0192(7) 0.0183(8) -0.0007(6) -0.0034(6) 0.0022(6)
C4 0.0222(8) 0.0214(7) 0.0253(9) 0.0022(6) -0.0009(7) -0.0017(6)
C5 0.0213(8) 0.0318(8) 0.0233(9) 0.0027(7) 0.0034(7) -0.0011(7)
C6 0.0236(8) 0.0280(8) 0.0249(9) -0.0029(7) 0.0019(7) 0.0073(7)
C7A 0.0172(7) 0.0188(7) 0.0192(8) 0.0004(6) -0.0024(6) 0.0007(6)
C7 0.0232(8) 0.0186(7) 0.0275(9) -0.0017(6) -0.0025(7) 0.0028(6)
C8 0.0186(7) 0.0209(7) 0.0258(9) -0.0045(6) 0.0016(6) -0.0001(6)
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'
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
_geom_angle_publ_flag
C2 N1 C7A 104.89(11) . . ?
N1 C2 N3 113.00(12) . . ?
N1 C2 C8 125.22(13) . . ?
N3 C2 C8 121.77(13) . . ?
C2 N3 C3A 107.11(12) . . ?
N3 C3A C4 132.12(14) . . ?
N3 C3A C7A 105.39(12) . . ?
C4 C3A C7A 122.45(14) . . ?
C5 C4 C3A 116.82(14) . . ?
C4 C5 C6 121.14(14) . . ?
C7 C6 C5 121.77(14) . . ?
N1 C7A C7 130.21(13) . . ?
N1 C7A C3A 109.61(12) . . ?
C7 C7A C3A 120.11(13) . . ?
C6 C7 C7A 117.70(14) . . ?
C2 C8 C8 112.12(15) . 5_665 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3238(17) . ?
N1 C7A 1.3955(18) . ?
C2 N3 1.3594(18) . ?
C2 C8 1.492(2) . ?
N3 C3A 1.3836(18) . ?
C3A C4 1.392(2) . ?
C3A C7A 1.402(2) . ?
C4 C5 1.385(2) . ?
C5 C6 1.407(2) . ?
C6 C7 1.380(2) . ?
C7A C7 1.396(2) . ?
C8 C8 1.532(3) 5_665 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 N1 0.88 1.99 2.8290(16) 158.2 8_655
