#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:00:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180367 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/36/7203651.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_7203651
loop_
_publ_author_name
'Łukasz Dobrzycki'
'Krzysztof Woźniak'
_publ_section_title
;
 On polymorphism and planarity of benzidine dihydrochloride
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              780
_journal_paper_doi               10.1039/b612605g
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C12 H14 Cl2 N2'
_chemical_formula_weight         257.15
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.459(3)
_cell_length_b                   6.0877(8)
_cell_length_c                   7.3074(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1221.5(3)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET)
(compiled Oct 25 2005,08:50:05)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET)
(compiled Oct 25 2005,08:50:05)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET)
(compiled Oct 25 2005,08:50:05)
;
_computing_molecular_graphics    Diamond
_computing_publication_material  SHELXTL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.6479
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KM4CCD
_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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            39654
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.97
_diffrn_standards_decay_%        2
_diffrn_standards_number         '1 frame'
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.28cycle2 beta (release 25-10-2005 CrysAlis171 .NET)
(compiled Oct 25 2005,08:50:05)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0397
_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)+(0.0727P)²+0.4919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1465
_reflns_number_gt                1231
_reflns_number_total             1783
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b612605g.txt
_cod_data_source_block           2_293
_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      Pbcn
_cod_database_code               7203651
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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
Cl1 Cl 0.205962(17) 0.25667(7) 0.13427(9) 0.0471(2) Uani 1 1 d . . .
N1 N 0.18138(6) 0.7513(3) 0.2234(3) 0.0415(4) Uani 1 1 d . . .
C1 C 0.12792(6) 0.7486(3) 0.2258(3) 0.0333(4) Uani 1 1 d . . .
C2 C 0.10198(6) 0.9283(3) 0.1667(3) 0.0389(5) Uani 1 1 d . . .
C3 C 0.05157(6) 0.9252(3) 0.1766(3) 0.0368(4) Uani 1 1 d . . .
C4 C 0.02694(6) 0.7434(3) 0.2448(2) 0.0290(4) Uani 1 1 d . . .
C5 C 0.05399(6) 0.5630(3) 0.3023(3) 0.0357(4) Uani 1 1 d . . .
C6 C 0.10440(6) 0.5656(3) 0.2943(3) 0.0381(5) Uani 1 1 d . . .
H1A H 0.1994(10) 0.636(6) 0.170(5) 0.080(10) Uiso 1 1 d . . .
H1B H 0.1994(10) 0.750(3) 0.340(4) 0.051(8) Uiso 1 1 d . . .
H1C H 0.1982(10) 0.852(6) 0.171(5) 0.080(11) Uiso 1 1 d . . .
H2 H 0.1178(8) 1.054(4) 0.119(3) 0.056(7) Uiso 1 1 d . . .
H3 H 0.0317(8) 1.053(4) 0.137(3) 0.048(6) Uiso 1 1 d . . .
H5 H 0.0357(8) 0.432(4) 0.355(3) 0.054(7) Uiso 1 1 d . . .
H6 H 0.1222(8) 0.441(4) 0.329(3) 0.054(7) Uiso 1 1 d . . .
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
Cl1 0.0267(3) 0.0333(3) 0.0813(4) -0.0011(2) -0.0082(2) -0.00082(17)
N1 0.0194(7) 0.0395(9) 0.0657(12) -0.0002(9) 0.0007(7) 0.0007(7)
C1 0.0188(7) 0.0365(9) 0.0445(10) -0.0027(8) 0.0009(7) -0.0003(6)
C2 0.0259(9) 0.0341(9) 0.0567(12) 0.0064(9) 0.0000(8) -0.0029(7)
C3 0.0240(8) 0.0350(9) 0.0514(11) 0.0059(8) -0.0025(7) 0.0003(7)
C4 0.0204(7) 0.0344(9) 0.0321(8) -0.0015(8) -0.0008(6) 0.0001(7)
C5 0.0252(8) 0.0347(9) 0.0473(11) 0.0054(8) 0.0033(7) 0.0001(7)
C6 0.0269(9) 0.0352(9) 0.0523(12) 0.0046(9) 0.0004(8) 0.0047(7)
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1A 121.3(18) . . ?
C1 N1 H1B 119.4(16) . . ?
H1A N1 H1B 95(2) . . ?
C1 N1 H1C 123(2) . . ?
H1A N1 H1C 94(3) . . ?
H1B N1 H1C 97(2) . . ?
C2 C1 C6 120.88(17) . . ?
C2 C1 N1 120.33(17) . . ?
C6 C1 N1 118.74(16) . . ?
C1 C2 C3 119.36(18) . . ?
C1 C2 H2 121.3(14) . . ?
C3 C2 H2 119.3(14) . . ?
C2 C3 C4 121.01(17) . . ?
C2 C3 H3 121.5(13) . . ?
C4 C3 H3 117.5(13) . . ?
C3 C4 C5 118.51(16) . . ?
C3 C4 C4 120.30(12) . 3 ?
C5 C4 C4 121.19(12) . 3 ?
C6 C5 C4 120.81(17) . . ?
C6 C5 H5 121.1(13) . . ?
C4 C5 H5 118.0(13) . . ?
C1 C6 C5 119.42(17) . . ?
C1 C6 H6 120.4(14) . . ?
C5 C6 H6 120.1(14) . . ?
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 C1 1.468(2) . ?
N1 H1A 0.94(3) . ?
N1 H1B 0.99(3) . ?
N1 H1C 0.86(3) . ?
C1 C2 1.375(3) . ?
C1 C6 1.382(3) . ?
C2 C3 1.386(2) . ?
C2 H2 0.94(3) . ?
C3 C4 1.390(2) . ?
C3 H3 0.99(2) . ?
C4 C5 1.391(2) . ?
C4 C4 1.481(3) 3 ?
C5 C6 1.386(2) . ?
C5 H5 1.02(2) . ?
C6 H6 0.94(2) . ?
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
N1 H1B Cl1 0.99(3) 2.16(3) 3.078(2) 155(2) 7_566
N1 H1C Cl1 0.86(3) 2.48(4) 3.2161(19) 143(3) 1_565
N1 H1C Cl1 0.86(3) 2.71(3) 3.1614(18) 114(3) 8_665
N1 H1A Cl1 0.94(3) 2.33(4) 3.1540(18) 145(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(3) . . . . ?
N1 C1 C2 C3 -177.6(2) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C4 C4 179.7(2) . . . 3 ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C4 C5 C6 -179.1(2) 3 . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
N1 C1 C6 C5 178.19(19) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
