#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/72/2017208.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_2017208
loop_
_publ_author_name
'Seidel, Rüdiger W.'
'Sheldrick, William S.'
'Kolev, Tsonko M.'
'Koleva, Bojidarka B.'
_publ_section_title
;N,N-Diethyl-N'-[(E)-4-pyridylmethylene]benzene-1,4-diamine:
 a combined X-ray and density functional theory study
;
_journal_coeditor_code           BM3080
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o385
_journal_page_last               o387
_journal_paper_doi               10.1107/S0108270109025475
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H19 N3'
_chemical_formula_moiety         'C16 H19 N3'
_chemical_formula_sum            'C16 H19 N3'
_chemical_formula_weight         253.34
_chemical_name_systematic
;
N,N-Diethyl-N'-[(E)-4-pyridylmethylene]benzene-
1,4-diamine
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7984(5)
_cell_length_b                   14.8116(6)
_cell_length_c                   7.2524(3)
_cell_measurement_reflns_used    3166
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.7336
_cell_measurement_theta_min      2.7450
_cell_volume                     1374.80(10)
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2008)'
_computing_publication_material  'enCIFer (Allen et al.,  2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 8.4171
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur2'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10508
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
ABSPACK in CrysAlisPro (Oxford Diffraction, 2009)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'elongated prism'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1458
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0301
_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)+(0.0314P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0582
_reflns_number_gt                1069
_reflns_number_total             1458
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3080.cif
_cod_data_source_block           I
_cod_database_code               2017208
_cod_database_fobs_code          2017208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.34770(13) 0.86781(9) 0.4949(3) 0.0205(4) Uani d . 1 . .
N N4 0.34535(13) 0.48833(10) 0.4434(2) 0.0201(4) Uani d . 1 . .
C C1 0.34786(17) 0.77495(11) 0.4857(3) 0.0169(4) Uani d . 1 . .
C C2 0.41766(15) 0.72274(12) 0.5929(3) 0.0181(5) Uani d . 1 . .
H H2 0.4653 0.7523 0.6733 0.022 Uiso calc R 1 . .
C C3 0.41789(16) 0.63026(13) 0.5829(3) 0.0184(5) Uani d . 1 . .
H H3 0.4651 0.5972 0.6581 0.022 Uiso calc R 1 . .
C C4 0.35054(17) 0.58332(11) 0.4651(3) 0.0169(5) Uani d . 1 . .
C C5 0.28002(16) 0.63465(12) 0.3626(3) 0.0194(5) Uani d . 1 . .
H H5 0.2316 0.6046 0.2845 0.023 Uiso calc R 1 . .
C C6 0.27831(17) 0.72731(12) 0.3711(3) 0.0186(5) Uani d . 1 . .
H H6 0.2293 0.7598 0.2983 0.022 Uiso calc R 1 . .
C C7 0.41671(16) 0.91673(12) 0.6207(3) 0.0211(5) Uani d . 1 . .
H H7A 0.4228 0.8824 0.7372 0.025 Uiso calc R 1 . .
H H7B 0.3850 0.9760 0.6499 0.025 Uiso calc R 1 . .
C C8 0.52491(16) 0.93176(13) 0.5419(3) 0.0282(5) Uani d . 1 . .
H H8A 0.5567 0.8734 0.5120 0.042 Uiso calc R 1 . .
H H8B 0.5683 0.9632 0.6330 0.042 Uiso calc R 1 . .
H H8C 0.5198 0.9684 0.4298 0.042 Uiso calc R 1 . .
C C9 0.28284(16) 0.92364(13) 0.3752(3) 0.0217(5) Uani d . 1 . .
H H9A 0.2765 0.8939 0.2534 0.026 Uiso calc R 1 . .
H H9B 0.3177 0.9826 0.3564 0.026 Uiso calc R 1 . .
C C10 0.17398(16) 0.93977(13) 0.4529(3) 0.0287(6) Uani d . 1 . .
H H10A 0.1361 0.8823 0.4592 0.043 Uiso calc R 1 . .
H H10B 0.1361 0.9817 0.3727 0.043 Uiso calc R 1 . .
H H10C 0.1796 0.9656 0.5769 0.043 Uiso calc R 1 . .
N N11 0.39597(15) 0.14779(10) 0.4753(3) 0.0244(4) Uani d . 1 . .
C C12 0.32821(18) 0.20199(13) 0.3868(3) 0.0242(6) Uani d . 1 . .
H H12 0.2750 0.1741 0.3153 0.029 Uiso calc R 1 . .
C C13 0.33026(17) 0.29515(12) 0.3923(3) 0.0206(6) Uani d . 1 . .
H H13 0.2798 0.3296 0.3269 0.025 Uiso calc R 1 . .
C C14 0.40765(17) 0.33775(11) 0.4955(3) 0.0184(5) Uani d . 1 . .
C C15 0.47914(17) 0.28272(12) 0.5879(3) 0.0209(5) Uani d . 1 . .
H H15 0.5335 0.3085 0.6599 0.025 Uiso calc R 1 . .
C C16 0.46958(19) 0.19013(13) 0.5728(3) 0.0242(5) Uani d . 1 . .
H H16 0.5191 0.1539 0.6365 0.029 Uiso calc R 1 . .
C C17 0.41526(15) 0.43628(13) 0.5119(3) 0.0179(5) Uani d . 1 . .
H H17 0.4732 0.4620 0.5747 0.021 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C9 . . 122.57(19) ?
C1 N1 C7 . . 121.64(18) ?
C9 N1 C7 . . 115.73(14) ?
C17 N4 C4 . . 121.43(18) ?
N1 C1 C6 . . 121.9(2) ?
N1 C1 C2 . . 121.4(2) ?
C6 C1 C2 . . 116.74(14) ?
C3 C2 C1 . . 121.23(19) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C2 C3 C4 . . 121.82(19) ?
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C5 C4 C3 . . 116.96(15) ?
C5 C4 N4 . . 116.84(19) ?
C3 C4 N4 . . 126.18(18) ?
C6 C5 C4 . . 122.1(2) ?
C6 C5 H5 . . 119.0 ?
C4 C5 H5 . . 119.0 ?
C5 C6 C1 . . 121.13(19) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
N1 C7 C8 . . 112.96(18) ?
N1 C7 H7A . . 109.0 ?
C8 C7 H7A . . 109.0 ?
N1 C7 H7B . . 109.0 ?
C8 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N1 C9 C10 . . 112.95(19) ?
N1 C9 H9A . . 109.0 ?
C10 C9 H9A . . 109.0 ?
N1 C9 H9B . . 109.0 ?
C10 C9 H9B . . 109.0 ?
H9A C9 H9B . . 107.8 ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C16 N11 C12 . . 115.32(17) ?
N11 C12 C13 . . 124.8(2) ?
N11 C12 H12 . . 117.6 ?
C13 C12 H12 . . 117.6 ?
C12 C13 C14 . . 118.8(2) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C13 C14 C15 . . 117.34(17) ?
C13 C14 C17 . . 122.78(19) ?
C15 C14 C17 . . 119.9(2) ?
C16 C15 C14 . . 118.9(2) ?
C16 C15 H15 . . 120.5 ?
C14 C15 H15 . . 120.5 ?
N11 C16 C15 . . 124.8(2) ?
N11 C16 H16 . . 117.6 ?
C15 C16 H16 . . 117.6 ?
N4 C17 C14 . . 121.37(18) ?
N4 C17 H17 . . 119.3 ?
C14 C17 H17 . . 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.377(2) ?
N1 C9 . 1.458(3) ?
N1 C7 . 1.462(2) ?
N4 C17 . 1.281(2) ?
N4 C4 . 1.417(2) ?
C1 C6 . 1.408(3) ?
C1 C2 . 1.414(3) ?
C2 C3 . 1.372(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.399(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.395(3) ?
C5 C6 . 1.374(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.514(3) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C10 . 1.522(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
N11 C16 . 1.334(3) ?
N11 C12 . 1.345(3) ?
C12 C13 . 1.381(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.393(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.397(3) ?
C14 C17 . 1.467(2) ?
C15 C16 . 1.381(2) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 Cg1 2_665 0.95 2.83 3.700(2) 153
C6 H6 Cg1 4_554 0.95 2.84 3.633(2) 142
C12 H12 Cg2 4_544 0.95 2.92 3.754(2) 147
C15 H15 Cg2 2_665 0.95 2.75 3.623(2) 152
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24726476
