#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/75/2017509.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_2017509
loop_
_publ_author_name
'Kuś, Piotr'
'Borek, Jerzy'
'Jones, Peter G.'
_publ_section_title
;
 Two concomitant polymorphs of
 N,N'-bis[4-(diethylamino)phenyl]terephthaldiamide
;
_journal_coeditor_code           GD3326
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o93
_journal_page_last               o96
_journal_paper_doi               10.1107/S0108270110001952
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C28 H34 N4 O2'
_chemical_formula_moiety         'C28 H34 N4 O2'
_chemical_formula_sum            'C28 H34 N4 O2'
_chemical_formula_weight         458.59
_chemical_name_systematic
;
N,N'-bis[4-(diethylamino)phenyl]terephthaldiamide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.54(2)
_cell_angle_beta                 93.90(2)
_cell_angle_gamma                103.53(2)
_cell_formula_units_Z            1
_cell_length_a                   5.1100(9)
_cell_length_b                   9.946(3)
_cell_length_c                   12.107(3)
_cell_measurement_reflns_used    3618
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.9610
_cell_measurement_theta_min      3.7370
_cell_volume                     584.2(3)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3648
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Nova O'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4870
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         72.56
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       plate
_exptl_crystal_F_000             246
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         4870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0529
_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)+(0.1021P)²+0.1859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1615
_reflns_number_gt                4407
_reflns_number_total             4870
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3326.cif
_cod_data_source_block           It
_cod_database_code               2017509
_cod_database_fobs_code          2017509
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C C1 0.5038(2) 0.88397(12) 0.54926(10) 0.0251(3) Uani d . 1 . .
C C2 0.2791(2) 0.88202(13) 0.47505(10) 0.0258(3) Uani d . 1 . .
H H2 0.1287 0.8017 0.4580 0.031 Uiso calc R 1 . .
C C3 0.7222(2) 1.00224(13) 0.57320(10) 0.0268(3) Uani d . 1 . .
H H3 0.8746 1.0037 0.6234 0.032 Uiso calc R 1 . .
C C4 0.5222(2) 0.76179(12) 0.60342(10) 0.0255(3) Uani d . 1 . .
C C5 0.2607(2) 0.56035(12) 0.67321(10) 0.0259(3) Uani d . 1 . .
C C6 0.4141(2) 0.46253(12) 0.64875(10) 0.0266(3) Uani d . 1 . .
H H6 0.5392 0.4733 0.5945 0.032 Uiso calc R 1 . .
C C7 0.3865(2) 0.34990(13) 0.70258(10) 0.0267(3) Uani d . 1 . .
H H7 0.4953 0.2852 0.6850 0.032 Uiso calc R 1 . .
C C8 0.2031(2) 0.32801(12) 0.78224(10) 0.0256(3) Uani d . 1 . .
C C9 0.0475(3) 0.42747(13) 0.80512(11) 0.0293(3) Uani d . 1 . .
H H9 -0.0804 0.4164 0.8582 0.035 Uiso calc R 1 . .
C C10 0.0773(3) 0.54081(13) 0.75183(11) 0.0295(3) Uani d . 1 . .
H H10 -0.0297 0.6065 0.7693 0.035 Uiso calc R 1 . .
C C11 0.3357(3) 0.11204(13) 0.80000(11) 0.0292(3) Uani d . 1 . .
H H11A 0.5265 0.1602 0.8296 0.035 Uiso calc R 1 . .
H H11B 0.3242 0.0892 0.7164 0.035 Uiso calc R 1 . .
C C12 0.2560(3) -0.02507(14) 0.84292(12) 0.0378(3) Uani d . 1 . .
H H12A 0.2880 -0.0044 0.9257 0.057 Uiso calc R 1 . .
H H12B 0.3651 -0.0888 0.8120 0.057 Uiso calc R 1 . .
H H12C 0.0636 -0.0701 0.8186 0.057 Uiso calc R 1 . .
C C13 0.1203(3) 0.23087(14) 0.95289(11) 0.0324(3) Uani d . 1 . .
H H13A 0.0311 0.1386 0.9700 0.039 Uiso calc R 1 . .
H H13B -0.0054 0.2928 0.9657 0.039 Uiso calc R 1 . .
C C14 0.3763(3) 0.29584(15) 1.03466(12) 0.0375(3) Uani d . 1 . .
H H14A 0.4973 0.2322 1.0265 0.056 Uiso calc R 1 . .
H H14B 0.3291 0.3104 1.1123 0.056 Uiso calc R 1 . .
H H14C 0.4679 0.3868 1.0180 0.056 Uiso calc R 1 . .
N N1 0.2843(2) 0.67814(11) 0.61977(9) 0.0261(3) Uani d . 1 . .
H H01 0.139(4) 0.7019(17) 0.6137(13) 0.033(4) Uiso d . 1 . .
N N2 0.1648(2) 0.20924(11) 0.83312(9) 0.0273(3) Uani d . 1 . .
O O1 0.74457(17) 0.74183(9) 0.63127(8) 0.0296(2) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 C1 C2 . . 119.45(11) ?
C3 C1 C4 . . 117.76(11) ?
C2 C1 C4 . . 122.78(11) ?
C3 C2 C1 2_676 . 119.65(12) ?
C2 C3 C1 2_676 . 120.90(11) ?
O1 C4 N1 . . 123.20(10) ?
O1 C4 C1 . . 120.61(11) ?
N1 C4 C1 . . 116.19(10) ?
C10 C5 C6 . . 118.36(11) ?
C10 C5 N1 . . 119.41(10) ?
C6 C5 N1 . . 122.24(11) ?
C7 C6 C5 . . 120.61(11) ?
C6 C7 C8 . . 122.09(10) ?
C7 C8 C9 . . 116.48(11) ?
C7 C8 N2 . . 122.18(10) ?
C9 C8 N2 . . 121.26(11) ?
C10 C9 C8 . . 121.31(11) ?
C9 C10 C5 . . 121.15(10) ?
N2 C11 C12 . . 113.44(11) ?
N2 C13 C14 . . 114.45(11) ?
C4 N1 C5 . . 124.43(10) ?
C8 N2 C13 . . 117.29(10) ?
C8 N2 C11 . . 115.79(10) ?
C13 N2 C11 . . 114.75(9) ?
C3 C2 H2 2_676 . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 H3 2_676 . 119.5 ?
C1 C3 H3 . . 119.5 ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 H7 . . 119.0 ?
C8 C7 H7 . . 119.0 ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
C9 C10 H10 . . 119.4 ?
C5 C10 H10 . . 119.4 ?
N2 C11 H11A . . 108.9 ?
C12 C11 H11A . . 108.9 ?
N2 C11 H11B . . 108.9 ?
C12 C11 H11B . . 108.9 ?
H11A C11 H11B . . 107.7 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N2 C13 H13A . . 108.6 ?
C14 C13 H13A . . 108.6 ?
N2 C13 H13B . . 108.6 ?
C14 C13 H13B . . 108.6 ?
H13A C13 H13B . . 107.6 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C4 N1 H01 . . 122.0(11) ?
C5 N1 H01 . . 112.0(11) ?
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
C1 C3 . 1.3894(19) ?
C1 C2 . 1.4030(19) ?
C1 C4 . 1.5008(16) ?
C2 C3 2_676 1.3841(17) ?
C3 C2 2_676 1.3841(17) ?
C4 O1 . 1.2336(15) ?
C4 N1 . 1.3527(17) ?
C5 C10 . 1.3878(18) ?
C5 C6 . 1.3901(17) ?
C5 N1 . 1.4239(16) ?
C6 C7 . 1.3803(17) ?
C7 C8 . 1.3999(18) ?
C8 C9 . 1.4091(17) ?
C8 N2 . 1.4098(16) ?
C9 C10 . 1.3818(18) ?
C11 N2 . 1.4693(15) ?
C11 C12 . 1.5245(18) ?
C13 N2 . 1.4676(17) ?
C13 C14 . 1.518(2) ?
C2 H2 . 0.9500 ?
C3 H3 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 H12A . 0.9800 ?
C12 H12B . 0.9800 ?
C12 H12C . 0.9800 ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
N1 H01 . 0.832(18) ?
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
N1 H01 O1 1_455 0.832(18) 2.161(18) 2.9773(14) 166.8(14)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 C1 C2 C3 . . . 2_676 -0.07(18) ?
C4 C1 C2 C3 . . . 2_676 -179.00(10) ?
C2 C1 C3 C2 . . . 2_676 0.07(18) ?
C4 C1 C3 C2 . . . 2_676 179.06(10) ?
C3 C1 C4 O1 . . . . -26.53(16) ?
C2 C1 C4 O1 . . . . 152.42(12) ?
C3 C1 C4 N1 . . . . 153.02(11) ?
C2 C1 C4 N1 . . . . -28.03(16) y
C10 C5 C6 C7 . . . . -0.79(19) ?
N1 C5 C6 C7 . . . . 179.76(12) ?
C5 C6 C7 C8 . . . . 0.7(2) ?
C6 C7 C8 C9 . . . . -0.13(19) ?
C6 C7 C8 N2 . . . . 176.75(12) ?
C7 C8 C9 C10 . . . . -0.44(19) ?
N2 C8 C9 C10 . . . . -177.35(12) ?
C8 C9 C10 C5 . . . . 0.4(2) ?
C6 C5 C10 C9 . . . . 0.2(2) ?
N1 C5 C10 C9 . . . . 179.70(12) ?
O1 C4 N1 C5 . . . . 1.76(19) ?
C1 C4 N1 C5 . . . . -177.78(10) y
C10 C5 N1 C4 . . . . 136.23(13) ?
C6 C5 N1 C4 . . . . -44.32(18) y
C7 C8 N2 C13 . . . . 142.46(13) ?
C9 C8 N2 C13 . . . . -40.81(17) ?
C7 C8 N2 C11 . . . . 1.87(18) ?
C9 C8 N2 C11 . . . . 178.60(11) ?
C14 C13 N2 C8 . . . . -79.16(13) ?
C14 C13 N2 C11 . . . . 61.83(14) ?
C12 C11 N2 C8 . . . . -171.05(11) ?
C12 C11 N2 C13 . . . . 47.36(15) ?
