#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/08/2010858.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2010858
loop_
_publ_author_name
'Boyer, Isabelle'
'Quillard, Sophie'
'Corraze, Benoit'
'Deniard, Philippe'
'Evain, Michel'
_publ_section_title
;
 A second polymorphic form of
 N,N'-diphenyl-1,4-phenylenediamine
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e159
_journal_page_last               e159
_journal_paper_doi               10.1107/S0108270100003498
_journal_volume                  56
_journal_year                    2000
_chemical_formula_iupac          'C18 H16 N2'
_chemical_formula_moiety         'C18 H16 N2'
_chemical_formula_sum            'C18 H16 N2'
_chemical_formula_weight         260.3
_chemical_melting_point          426
_chemical_name_systematic        ' N,N'-diphenyl-1,4-phenylenediamine'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                108.56(3)
_cell_angle_beta                 94.60(3)
_cell_angle_gamma                112.38(3)
_cell_formula_units_Z            2
_cell_length_a                   7.911(2)
_cell_length_b                   8.984(2)
_cell_length_c                   11.133(3)
_cell_measurement_reflns_used    1631
_cell_measurement_temperature    150
_cell_measurement_theta_max      24
_cell_measurement_theta_min      2
_cell_volume                     675.0(4)
_computing_cell_refinement       'CELL (Stoe & Cie, 1996)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 1996)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 1996)'
_computing_publication_material  JANA98
_computing_structure_refinement  'JANA98 (Petricek & Dusek, 1998)'
_computing_structure_solution    'SIR97 (Altomare et al., 1997)'
_diffrn_ambient_temperature      150
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .057
_diffrn_reflns_av_sigmaI/netI    .0337
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7072
_diffrn_reflns_theta_max         23.95
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.28
_exptl_crystal_description       plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .08
_refine_diff_density_max         .12
_refine_diff_density_min         -.14
_refine_ls_extinction_coef       .90(10)
_refine_ls_extinction_method     'B-C type 1, Lorentzian isotropic'
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     189
_refine_ls_number_reflns         1931
_refine_ls_R_factor_all          .046
_refine_ls_R_factor_gt           .030
_refine_ls_shift/su_max          .0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(I) + 0.0016I²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_ref         .069
_reflns_number_gt                1450
_reflns_number_total             1931
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            qa0242.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '150K' was changed to '150' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '150K' was changed to '150' - the
value should be numeric and without a unit designator.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2010858
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_type_symbol
N1a .9757(2) .2786(2) .19380(10) .0246(6) 1 N
C1a .9838(2) .1377(2) .09540(10) .0212(7) 1 C
C2a .8898(2) -.0334(2) .08780(10) .0229(7) 1 C
C3a 1.0941(2) .1682(2) .00650(10) .0228(7) 1 C
C4a .8117(2) .2858(2) .23190(10) .0219(7) 1 C
C5a .8313(2) .4327(2) .33480(10) .0277(7) 1 C
C6a .6747(2) .4486(2) .37390(10) .0339(8) 1 C
C7a .4952(2) .3163(2) .3122(2) .0338(8) 1 C
C8a .4758(2) .1693(2) .21130(10) .0296(7) 1 C
C9a .6314(2) .1520(2) .17060(10) .0253(7) 1 C
N1b .2353(2) .8286(2) .44660(10) .0295(6) 1 N
C1b .1150(2) .9122(2) .46980(10) .0233(7) 1 C
C2b .0982(2) 1.0165(2) .40390(10) .0263(7) 1 C
C3b .0147(2) .8973(2) .56560(10) .0260(7) 1 C
C4b .2884(2) .7699(2) .33050(10) .0245(7) 1 C
C5b .4530(2) .7453(2) .33420(10) .0302(8) 1 C
C6b .5105(2) .6891(2) .2208(2) .0359(8) 1 C
C7b .4076(2) .6574(2) .1012(2) .0323(8) 1 C
C8b .2413(2) .6755(2) .09670(10) .0296(7) 1 C
C9b .1796(2) .7289(2) .20910(10) .0260(7) 1 C
H1a 1.065(2) .381(2) .2090(10) .0360(10) 1 H
H1b .287(2) .820(2) .512(2) .036 1 H
H2a .810 -.060 .150 .036 1 H
H3a 1.163 .290 .010 .036 1 H
H5a .959 .528 .381 .036 1 H
H6a .691 .556 .447 .036 1 H
H7a .382 .326 .340 .036 1 H
H8a .347 .074 .167 .036 1 H
H9a .613 .044 .098 .036 1 H
H2b .168 1.030 .334 .036 1 H
H3b .024 .823 .614 .036 1 H
H5b .531 .768 .419 .036 1 H
H6b .628 .671 .225 .036 1 H
H7b .452 .622 .020 .036 1 H
H8b .164 .649 .011 .036 1 H
H9b .057 .738 .203 .036 1 H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .003 .002 International_Tables_Vol_C
N .006 .003 International_Tables_Vol_C
H .000 .000 International_Tables_Vol_C
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1a N1a C4a . . 126.10(10) no
C1a N1a H1a . . 116.0(10) no
C4a N1a H1a . . 113.0(10) no
N1a C1a C2a . . 121.50(10) no
N1a C1a C3a . . 120.00(10) no
C2a C1a C3a . . 118.40(10) no
C1a C2a C3a . 2_755 120.40(10) no
C1a C2a H2a . . 120.4 no
C3a C2a H2a 2_755 . 119.2 no
C1a C3a C2a . 2_755 121.2(2) no
C1a C3a H3a . . 119.8 no
C2a C3a H3a 2_755 . 119.0 no
N1a C4a C5a . . 118.20(10) no
N1a C4a C9a . . 123.00(10) no
C5a C4a C9a . . 118.8(2) no
C4a C5a C6a . . 120.60(10) no
C4a C5a H5a . . 119.9 no
C6a C5a H5a . . 119.5 no
C5a C6a C7a . . 120.6(2) no
C5a C6a H6a . . 119.5 no
C7a C6a H6a . . 119.9 no
C6a C7a C8a . . 118.8(2) no
C6a C7a H7a . . 121.2 no
C8a C7a H7a . . 120.0 no
C7a C8a C9a . . 121.20(10) no
C7a C8a H8a . . 118.9 no
C9a C8a H8a . . 119.9 no
C4a C9a C8a . . 120.00(10) no
C4a C9a H9a . . 120.4 no
C8a C9a H9a . . 119.6 no
C1b N1b C4b . . 127.3(2) no
C1b N1b H1b . . 116.0(10) no
C4b N1b H1b . . 116.0(10) no
N1b C1b C2b . . 122.60(10) no
N1b C1b C3b . . 119.3(2) no
C2b C1b C3b . . 118.0(2) no
C1b C2b C3b . 2_576 120.5(2) no
C1b C2b H2b . . 120.1 no
C3b C2b H2b 2_576 . 119.4 no
C1b C3b C2b . 2_576 121.5(2) no
C1b C3b H3b . . 119.4 no
C2b C3b H3b 2_576 . 119.1 no
N1b C4b C5b . . 119.30(10) no
N1b C4b C9b . . 122.3(2) no
C5b C4b C9b . . 118.30(10) no
C4b C5b C6b . . 120.6(2) no
C4b C5b H5b . . 120.3 no
C6b C5b H5b . . 119.0 no
C5b C6b C7b . . 120.9(2) no
C5b C6b H6b . . 119.4 no
C7b C6b H6b . . 119.7 no
C6b C7b C8b . . 118.6(2) no
C6b C7b H7b . . 120.9 no
C8b C7b H7b . . 120.5 no
C7b C8b C9b . . 121.4(2) no
C7b C8b H8b . . 119.1 no
C9b C8b H8b . . 119.5 no
C4b C9b C8b . . 120.0(2) no
C4b C9b H9b . . 120.4 no
C8b C9b H9b . . 119.6 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1a C1a . . 1.413(2) no
N1a C4a . . 1.415(2) no
N1a H1a . . .87(2) no
C1a C2a . . 1.400(2) no
C1a C3a . . 1.395(2) no
C2a C3a . 2_755 1.384(2) no
C2a H2a . . 1.000 no
C3a H3a . . 1.000 no
C4a C5a . . 1.390(2) no
C4a C9a . . 1.400(2) no
C5a C6a . . 1.388(3) no
C5a H5a . . .998 no
C6a C7a . . 1.393(2) no
C6a H6a . . .999 no
C7a C8a . . 1.379(2) no
C7a H7a . . .999 no
C8a C9a . . 1.390(2) no
C8a H8a . . .999 no
C9a H9a . . .999 no
N1b C1b . . 1.413(3) no
N1b C4b . . 1.395(2) no
N1b H1b . . .85(2) no
C1b C2b . . 1.397(3) no
C1b C3b . . 1.390(2) no
C2b C3b . 2_576 1.386(3) no
C2b H2b . . 1.000 no
C3b H3b . . 1.000 no
C4b C5b . . 1.401(3) no
C4b C9b . . 1.400(2) no
C5b C6b . . 1.384(2) no
C5b H5b . . .998 no
C6b C7b . . 1.388(3) no
C6b H6b . . 1.000 no
C7b C8b . . 1.385(3) no
C7b H7b . . .998 no
C8b C9b . . 1.389(2) no
C8b H8b . . .999 no
C9b H9b . . .999 no
