#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/54/2015449.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_2015449
loop_
_publ_author_name
'Ossowski, Jerzy'
'Kuś, Piotr'
'Näther, Christian'
'Jones, Peter G.'
_publ_section_title
;
 Two polymorphs of N,N'-diphenethylterephthalamide
;
_journal_coeditor_code           LN3008
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o369
_journal_page_last               o371
_journal_paper_doi               10.1107/S0108270106017422
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C24 H24 N2 O2'
_chemical_formula_moiety         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45
_chemical_name_systematic
;
N,N'-Diphenethylterephthalamide
;
_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                95.305(5)
_cell_angle_beta                 98.541(5)
_cell_angle_gamma                101.663(5)
_cell_formula_units_Z            1
_cell_length_a                   5.1845(12)
_cell_length_b                   9.719(2)
_cell_length_c                   10.041(2)
_cell_measurement_reflns_used    3748
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.79
_cell_volume                     486.07(18)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      133(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0374
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5728
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         2.07
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0464
_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)+(0.0648P)²+0.1016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                2271
_reflns_number_total             2899
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ln3008.cif
_cod_data_source_block           T
_cod_original_cell_volume        486.08(18)
_cod_database_code               2015449
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
O O1 0.20205(16) 0.32616(10) 0.26726(9) 0.0277(2) Uani d . 1
N N1 0.63551(19) 0.30544(11) 0.29535(11) 0.0245(2) Uani d . 1
H H1 0.783(3) 0.3201(16) 0.2636(16) 0.030(4) Uiso d . 1
C C1 0.4699(2) 0.42616(11) 0.11183(11) 0.0183(2) Uani d . 1
C C2 0.7147(2) 0.51500(12) 0.10553(11) 0.0200(2) Uani d . 1
H H2 0.8614 0.5254 0.1775 0.024 Uiso calc R 1
C C3 0.2556(2) 0.41176(12) 0.00574(12) 0.0207(2) Uani d . 1
H H3 0.0886 0.3516 0.0096 0.025 Uiso calc R 1
C C4 0.4242(2) 0.34843(12) 0.23175(11) 0.0199(2) Uani d . 1
C C5 0.6235(2) 0.22751(13) 0.41224(12) 0.0252(2) Uani d . 1
H H5A 0.6548 0.1319 0.3879 0.030 Uiso calc R 1
H H5B 0.4423 0.2159 0.4359 0.030 Uiso calc R 1
C C6 0.8290(3) 0.30203(14) 0.53544(13) 0.0292(3) Uani d . 1
H H6A 1.0106 0.3154 0.5120 0.035 Uiso calc R 1
H H6B 0.7953 0.3966 0.5622 0.035 Uiso calc R 1
C C7 0.8129(2) 0.21525(12) 0.65279(11) 0.0219(2) Uani d . 1
C C8 0.9578(2) 0.10983(13) 0.66794(12) 0.0262(3) Uani d . 1
H H8 1.0736 0.0944 0.6058 0.031 Uiso calc R 1
C C9 0.9343(3) 0.02702(14) 0.77316(14) 0.0310(3) Uani d . 1
H H9 1.0340 -0.0445 0.7824 0.037 Uiso calc R 1
C C10 0.7663(3) 0.04841(15) 0.86445(13) 0.0324(3) Uani d . 1
H H10 0.7497 -0.0086 0.9360 0.039 Uiso calc R 1
C C11 0.6226(3) 0.15343(15) 0.85077(13) 0.0322(3) Uani d . 1
H H11 0.5082 0.1691 0.9135 0.039 Uiso calc R 1
C C12 0.6454(2) 0.23592(13) 0.74555(13) 0.0274(3) Uani d . 1
H H12 0.5454 0.3074 0.7368 0.033 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C4 N1 C5 . 122.93(9) ?
C3 C1 C2 . 119.48(10) ?
C3 C1 C4 . 118.12(9) y
C2 C1 C4 . 122.36(9) y
C3 C2 C1 2_665 120.19(10) ?
C2 C3 C1 2_665 120.33(10) ?
O1 C4 N1 . 123.30(10) ?
O1 C4 C1 . 120.55(9) ?
N1 C4 C1 . 116.15(9) ?
N1 C5 C6 . 112.32(10) ?
C7 C6 C5 . 110.25(10) ?
C12 C7 C8 . 118.48(11) ?
C12 C7 C6 . 120.52(11) ?
C8 C7 C6 . 120.96(11) ?
C9 C8 C7 . 120.61(12) ?
C10 C9 C8 . 120.30(12) ?
C9 C10 C11 . 119.55(12) ?
C10 C11 C12 . 120.19(12) ?
C11 C12 C7 . 120.87(12) ?
C4 N1 H1 . 119.3(10) ?
C5 N1 H1 . 117.7(10) ?
C3 C2 H2 2_665 119.9 ?
C1 C2 H2 . 119.9 ?
C2 C3 H3 2_665 119.8 ?
C1 C3 H3 . 119.8 ?
N1 C5 H5A . 109.1 ?
C6 C5 H5A . 109.1 ?
N1 C5 H5B . 109.1 ?
C6 C5 H5B . 109.1 ?
H5A C5 H5B . 107.9 ?
C7 C6 H6A . 109.6 ?
C5 C6 H6A . 109.6 ?
C7 C6 H6B . 109.6 ?
C5 C6 H6B . 109.6 ?
H6A C6 H6B . 108.1 ?
C9 C8 H8 . 119.7 ?
C7 C8 H8 . 119.7 ?
C10 C9 H9 . 119.8 ?
C8 C9 H9 . 119.8 ?
C9 C10 H10 . 120.2 ?
C11 C10 H10 . 120.2 ?
C10 C11 H11 . 119.9 ?
C12 C11 H11 . 119.9 ?
C11 C12 H12 . 119.6 ?
C7 C12 H12 . 119.6 ?
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
O1 C4 . 1.2395(13) y
N1 C4 . 1.3449(14) y
N1 C5 . 1.4568(14) y
C1 C3 . 1.3953(15) ?
C1 C2 . 1.3971(15) ?
C1 C4 . 1.5023(15) ?
C2 C3 2_665 1.3901(15) ?
C3 C2 2_665 1.3901(15) ?
C5 C6 . 1.5235(17) y
C6 C7 . 1.5137(16) y
C7 C12 . 1.3920(17) ?
C7 C8 . 1.3940(17) ?
C8 C9 . 1.3909(18) ?
C9 C10 . 1.385(2) ?
C10 C11 . 1.385(2) ?
C11 C12 . 1.3886(18) ?
N1 H1 . 0.864(16) ?
C2 H2 . 0.9500 ?
C3 H3 . 0.9500 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 H12 . 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
N1 H1 O1 1_655 0.864(16) 2.155(16) 2.9606(14) 155.1(14)
C6 H6A O1 1_655 0.99 2.79 3.5395(17) 133
C9 H9 O1 2_656 0.95 2.73 3.3351(18) 122
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_4
_geom_torsion
_geom_torsion_publ_flag
C3 C1 C2 C3 2_665 -0.10(18) ?
C4 C1 C2 C3 2_665 -177.89(10) ?
C2 C1 C3 C2 2_665 0.10(18) ?
C4 C1 C3 C2 2_665 177.99(10) ?
C5 N1 C4 O1 . 0.33(19) ?
C5 N1 C4 C1 . -179.32(11) y
C3 C1 C4 O1 . -31.21(16) y
C2 C1 C4 O1 . 146.61(12) ?
C3 C1 C4 N1 . 148.45(11) ?
C2 C1 C4 N1 . -33.72(16) ?
C4 N1 C5 C6 . -122.89(13) ?
N1 C5 C6 C7 . -178.62(10) y
C5 C6 C7 C12 . -90.35(14) ?
C5 C6 C7 C8 . 87.46(14) y
C12 C7 C8 C9 . 0.24(17) ?
C6 C7 C8 C9 . -177.61(11) ?
C7 C8 C9 C10 . -0.03(19) ?
C8 C9 C10 C11 . -0.35(19) ?
C9 C10 C11 C12 . 0.51(19) ?
C10 C11 C12 C7 . -0.30(19) ?
C8 C7 C12 C11 . -0.08(17) ?
C6 C7 C12 C11 . 177.78(11) ?
