#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/68/1506845.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_1506845
loop_
_publ_author_name
'Nishiumi, Toyohiko'
'Nomura, Yasuhiro'
'Chimoto, Yuya'
'Higuchi, Masayoshi'
'Yamamoto, Kimihisa'
_publ_section_title
;
 The Class II/III Transition Electron Transfer on an Infrared Vibrational
 Time Scale forN,N‘-Diphenyl-1,4-phenylenediamine Structures
;
_journal_issue                   23
_journal_name_full               'The Journal of Physical Chemistry B'
_journal_page_first              7992
_journal_paper_doi               10.1021/jp0492265
_journal_volume                  108
_journal_year                    2004
_chemical_formula_moiety         'C22 H24 N2 '
_chemical_formula_sum            'C22 H24 N2'
_chemical_formula_weight         316.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             'Wed Sep 10 17:32:03 2003'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 103.46(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.062(1)
_cell_length_b                   14.302(2)
_cell_length_c                   7.977(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    297.2
_cell_measurement_theta_max      13.7
_cell_measurement_theta_min      10.1
_cell_volume                     894.5(2)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2428
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0.20
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1439
_refine_ls_R_factor_gt           0.060
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²) + (0.0943P)²+0.2429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.201
_reflns_number_gt                1439
_reflns_number_total             2060
_reflns_threshold_expression     I>2Σ(I)
_cod_data_source_file            jp0492265si20040220_043332.cif
_cod_data_source_block           26DMPDA
_cod_original_formula_sum        'C22 H24 N2 '
_cod_database_code               1506845
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-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_calc_flag
N(1) N 0.8245(2) 0.0473(1) 0.9546(2) 0.0597(5) Uani 1.00 d
C(2) C 0.4864(2) -0.0632(2) 1.1266(2) 0.0506(5) Uani 1.00 d
C(3) C 0.6453(2) -0.0393(1) 1.1017(2) 0.0499(5) Uani 1.00 d
C(4) C 0.6612(2) 0.0244(1) 0.9757(2) 0.0458(5) Uani 1.00 d
C(5) C 0.8552(2) 0.1007(2) 0.8153(2) 0.0502(5) Uani 1.00 d
C(6) C 0.9286(3) 0.1897(2) 0.8447(3) 0.0585(6) Uani 1.00 d
C(7) C 0.9657(3) 0.2377(2) 0.7060(4) 0.0712(7) Uani 1.00 d
C(8) C 0.9295(4) 0.1997(2) 0.5449(3) 0.0769(8) Uani 1.00 d
C(9) C 0.8575(3) 0.1126(2) 0.5172(3) 0.0695(7) Uani 1.00 d
C(10) C 0.8194(3) 0.0608(2) 0.6504(3) 0.0557(5) Uani 1.00 d
C(11) C 0.7454(4) -0.0356(2) 0.6169(3) 0.0721(7) Uani 1.00 d
C(12) C 0.9660(4) 0.2325(2) 1.0216(4) 0.0813(8) Uani 1.00 d
H(1) H 0.9038 0.0450 1.0450 0.0990 Uiso 1.00 calc
H(2) H 0.4741 -0.1080 1.2116 0.0990 Uiso 1.00 calc
H(3) H 0.7543 -0.0677 1.1838 0.0990 Uiso 1.00 calc
H(7) H 1.0124 0.3021 0.7259 0.0990 Uiso 1.00 calc
H(8) H 0.9458 0.2363 0.4444 0.0990 Uiso 1.00 calc
H(9) H 0.8360 0.0858 0.4104 0.0990 Uiso 1.00 calc
H(11A) H 0.6407 -0.0323 0.5342 0.0875 Uiso 1.00 calc
H(11B) H 0.8235 -0.0737 0.5739 0.0875 Uiso 1.00 calc
H(11C) H 0.7292 -0.0611 0.7211 0.0875 Uiso 1.00 calc
H(12A) H 0.8673 0.2282 1.0664 0.1027 Uiso 1.00 calc
H(12B) H 1.0585 0.2024 1.0928 0.1027 Uiso 1.00 calc
H(12C) H 0.9923 0.2977 1.0109 0.1027 Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;International Tables for Crystallography
(1992, 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
C(4) N(1) C(5) 124.0(1) . . yes
C(4) N(1) H(1) 115.7 . . no
C(5) N(1) H(1) 117.0 . . no
C(3) C(2) C(4) 120.7(2) . 3_657 yes
C(3) C(2) H(2) 121.3 . . no
C(4) C(2) H(2) 117.9 3_657 . no
C(2) C(3) C(4) 120.8(2) . . yes
C(2) C(3) H(3) 118.9 . . no
C(4) C(3) H(3) 120.2 . . no
N(1) C(4) C(2) 122.3(2) . 3_657 yes
N(1) C(4) C(3) 119.2(2) . . yes
C(2) C(4) C(3) 118.5(2) 3_657 . yes
N(1) C(5) C(6) 120.2(2) . . yes
N(1) C(5) C(10) 118.8(2) . . yes
C(6) C(5) C(10) 120.9(2) . . yes
C(5) C(6) C(7) 118.4(2) . . yes
C(5) C(6) C(12) 120.8(2) . . yes
C(7) C(6) C(12) 120.8(2) . . yes
C(6) C(7) C(8) 121.0(2) . . yes
C(6) C(7) H(7) 118.3 . . no
C(8) C(7) H(7) 120.7 . . no
C(7) C(8) C(9) 120.3(3) . . yes
C(7) C(8) H(8) 120.9 . . no
C(9) C(8) H(8) 118.7 . . no
C(8) C(9) C(10) 121.5(2) . . yes
C(8) C(9) H(9) 120.9 . . no
C(10) C(9) H(9) 117.5 . . no
C(5) C(10) C(9) 117.9(2) . . yes
C(5) C(10) C(11) 121.8(2) . . yes
C(9) C(10) C(11) 120.3(2) . . yes
C(10) C(11) H(11A) 109.4 . . no
C(10) C(11) H(11B) 108.7 . . no
C(10) C(11) H(11C) 109.2 . . no
H(11A) C(11) H(11B) 109.6 . . no
H(11A) C(11) H(11C) 110.5 . . no
H(11B) C(11) H(11C) 109.5 . . no
C(6) C(12) H(12A) 109.0 . . no
C(6) C(12) H(12B) 109.9 . . no
C(6) C(12) H(12C) 108.1 . . no
H(12A) C(12) H(12B) 111.3 . . no
H(12A) C(12) H(12C) 108.6 . . no
H(12B) C(12) H(12C) 109.9 . . no
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
N(1) C(4) 1.404(3) . yes
N(1) C(5) 1.417(3) . yes
N(1) H(1) 0.845 . no
C(2) C(3) 1.385(3) . yes
C(2) C(4) 1.391(3) 3_657 yes
C(2) H(2) 0.954 . no
C(3) C(4) 1.385(3) . yes
C(3) H(3) 1.048 . no
C(5) C(6) 1.400(3) . yes
C(5) C(10) 1.401(3) . yes
C(6) C(7) 1.392(4) . yes
C(6) C(12) 1.503(4) . yes
C(7) C(8) 1.362(4) . yes
C(7) H(7) 0.994 . no
C(8) C(9) 1.370(4) . yes
C(8) H(8) 0.991 . no
C(9) C(10) 1.387(4) . yes
C(9) H(9) 0.913 . no
C(10) C(11) 1.502(3) . yes
C(11) H(11A) 0.943 . no
C(11) H(11B) 0.955 . no
C(11) H(11C) 0.945 . no
C(12) H(12A) 0.947 . no
C(12) H(12B) 0.932 . no
C(12) H(12C) 0.964 . no
