#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/65/2206565.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_2206565
loop_
_publ_author_name
'Clive L. Oliver'
'Gareth O. Lloyd'
'Elise J.C. de Vries'
_publ_section_title
;
 N,N'-Bis(pyridin-4-ylmethyl)succinamide--terephthalic
 acid (1/1)
;
_journal_coeditor_code           TK6236
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2605
_journal_page_last               o2606
_journal_paper_doi               10.1107/S1600536805021227
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H18 N4 O2 , C8 H6 O4'
_chemical_formula_moiety         'C16 H18 N4 O2 , C8 H6 O4'
_chemical_formula_sum            'C24 H24 N4 O6'
_chemical_formula_weight         464.47
_chemical_name_systematic
;
N,N'-bis(pyridin-4-ylmethyl)succinamide--terephthalic acid (1/1)
;
_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
_cell_angle_alpha                96.582(4)
_cell_angle_beta                 95.944(4)
_cell_angle_gamma                94.753(4)
_cell_formula_units_Z            1
_cell_length_a                   4.8721(13)
_cell_length_b                   9.550(3)
_cell_length_c                   11.547(3)
_cell_measurement_reflns_used    2080
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.6
_cell_volume                     528.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'X-SEED (Atwood & Barbour, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       ω
_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  0.028
_diffrn_reflns_av_sigmaI/netI    0.048
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3480
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         28.2
_diffrn_reflns_theta_min         1.8
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.054
_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)+(0.0704P)²+0.3562P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.143
_refine_ls_wR_factor_ref         0.146
_reflns_number_gt                2156
_reflns_number_total             2330
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6236.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               2206565
_cod_database_fobs_code          2206565
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O9B 0.2812(2) 0.67174(13) 0.39791(11) 0.0206(3) Uani d . 1 . O
N4B -0.6616(3) 1.14377(14) 0.23942(12) 0.0171(3) Uani d . 1 . N
N8B -0.1477(3) 0.74241(14) 0.36740(12) 0.0159(3) Uani d . 1 . N
H5 -0.3203 0.7349 0.3838 0.019 Uiso calc R 1 . H
C1B -0.2717(3) 0.94885(17) 0.27306(14) 0.0154(3) Uani d . 1 . C
C5B -0.5089(3) 1.14620(18) 0.34315(15) 0.0192(4) Uani d . 1 . C
H11 -0.5347 1.2166 0.4052 0.023 Uiso calc R 1 . H
C2B -0.4285(3) 0.94767(17) 0.16569(14) 0.0169(3) Uani d . 1 . C
H12 -0.4041 0.8802 0.1014 0.020 Uiso calc R 1 . H
C3B -0.6207(3) 1.04521(17) 0.15246(14) 0.0178(3) Uani d . 1 . C
H13 -0.7282 1.0420 0.0785 0.021 Uiso calc R 1 . H
C9B 0.0341(3) 0.66138(17) 0.41422(15) 0.0178(3) Uani d . 1 . C
C6B -0.3153(3) 1.05104(18) 0.36435(15) 0.0189(4) Uani d . 1 . C
H15 -0.2139 1.0552 0.4397 0.023 Uiso calc R 1 . H
C7B -0.0619(3) 0.84318(17) 0.28929(15) 0.0181(4) Uani d . 1 . C
H16A -0.0393 0.7914 0.2121 0.022 Uiso calc R 1 . H
H16B 0.1197 0.8940 0.3224 0.022 Uiso calc R 1 . H
O1B 0.0119(3) 0.77301(13) -0.00313(11) 0.0215(3) Uani d . 1 . O
O1A 0.0453(2) 0.68403(12) -0.18870(10) 0.0192(3) Uani d . 1 . O
H3 -0.0690 0.7425 -0.2038 0.023 Uiso calc R 1 . H
C1A 0.1078(3) 0.69211(16) -0.07418(14) 0.0155(3) Uani d . 1 . C
C3A 0.3680(3) 0.57972(17) 0.08183(14) 0.0166(3) Uani d . 1 . C
H8 0.2768 0.6345 0.1374 0.020 Uiso calc R 1 . H
C2A 0.3118(3) 0.59200(16) -0.03722(14) 0.0147(3) Uani d . 1 . C
C4A 0.5558(2) 0.48835(14) 0.12034(12) 0.0161(3) Uani d . 1 . C
H10 0.5938 0.4805 0.2016 0.019 Uiso calc R 1 . H
C10B -0.0778(2) 0.56377(14) 0.49584(12) 0.0227(7) Uani d PR 0.858(7) 1 C
H10A -0.0698 0.6170 0.5751 0.027 Uiso calc PR 0.858(7) 1 H
H10B -0.2748 0.5325 0.4681 0.027 Uiso calc PR 0.858(7) 1 H
C11B -0.098(4) 0.511(2) 0.4419(17) 0.040 Uiso d P 0.142(7) 2 C
H11A -0.0852 0.4348 0.3771 0.048 Uiso calc PR 0.142(7) 2 H
H11B -0.2934 0.5137 0.4570 0.048 Uiso calc PR 0.142(7) 2 H
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_site_symmetry_3
_geom_angle
C3B N4B C5B . . 117.75(14)
C9B N8B C7B . . 120.40(13)
C9B N8B H5 . . 119.8
C7B N8B H5 . . 119.8
C2B C1B C6B . . 117.61(14)
C2B C1B C7B . . 120.55(14)
C6B C1B C7B . . 121.84(15)
N4B C5B C6B . . 123.18(15)
N4B C5B H11 . . 118.4
C6B C5B H11 . . 118.4
C3B C2B C1B . . 119.78(15)
C3B C2B H12 . . 120.1
C1B C2B H12 . . 120.1
N4B C3B C2B . . 122.75(15)
N4B C3B H13 . . 118.6
C2B C3B H13 . . 118.6
O9B C9B N8B . . 122.42(15)
O9B C9B C10B . . 121.97(14)
N8B C9B C10B . . 115.46(13)
O9B C9B C11B . . 117.4(7)
N8B C9B C11B . . 115.0(7)
C5B C6B C1B . . 118.92(15)
C5B C6B H15 . . 120.5
C1B C6B H15 . . 120.5
N8B C7B C1B . . 111.26(12)
N8B C7B H16A . . 109.4
C1B C7B H16A . . 109.4
N8B C7B H16B . . 109.4
C1B C7B H16B . . 109.4
H16A C7B H16B . . 108.0
C1A O1A H3 . . 109.5
O1B C1A O1A . . 124.10(14)
O1B C1A C2A . . 121.93(15)
O1A C1A C2A . . 113.97(13)
C4A C3A C2A . . 120.83(14)
C4A C3A H8 . . 119.6
C2A C3A H8 . . 119.6
C3A C2A C4A . 2_665 120.28(13)
C3A C2A C1A . . 118.75(14)
C4A C2A C1A 2_665 . 120.97(14)
C3A C4A C2A . 2_665 118.89(13)
C3A C4A H10 . . 120.6
C2A C4A H10 2_665 . 120.6
C10B C10B C9B 2_566 . 113.25(14)
C10B C10B H10A 2_566 . 108.9
C9B C10B H10A . . 108.9
C10B C10B H10B 2_566 . 108.9
C9B C10B H10B . . 108.9
H10A C10B H10B . . 107.7
C9B C11B C11B . 2_566 101.2(16)
C9B C11B H11A . . 111.5
C11B C11B H11A 2_566 . 111.5
C9B C11B H11B . . 111.5
C11B C11B H11B 2_566 . 111.5
H11A C11B H11B . . 109.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O9B C9B . 1.235(2)
N4B C3B . 1.338(2)
N4B C5B . 1.340(2)
N8B C9B . 1.337(2)
N8B C7B . 1.458(2)
N8B H5 . 0.8800
C1B C2B . 1.386(2)
C1B C6B . 1.398(2)
C1B C7B . 1.508(2)
C5B C6B . 1.386(2)
C5B H11 . 0.9500
C2B C3B . 1.384(2)
C2B H12 . 0.9500
C3B H13 . 0.9500
C9B C10B . 1.509(2)
C9B C11B . 1.607(18)
C6B H15 . 0.9500
C7B H16A . 0.9900
C7B H16B . 0.9900
O1B C1A . 1.217(2)
O1A C1A . 1.318(2)
O1A H3 . 0.8400
C1A C2A . 1.499(2)
C3A C4A . 1.391(2)
C3A C2A . 1.394(2)
C3A H8 . 0.9500
C2A C4A 2_665 1.403(2)
C4A C2A 2_665 1.403(2)
C4A H10 . 0.9500
C10B C10B 2_566 1.494(2)
C10B H10A . 0.9900
C10B H10B . 0.9900
C11B C11B 2_566 1.60(4)
C11B H11A . 0.9900
C11B H11B . 0.9900
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
N8B H5 O9B 1_455 0.88 2.01 2.875(2) 166
O1A H3 N4B 2_475 0.84 1.82 2.654(2) 175
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
C3B N4B C5B C6B . -0.8(2)
C6B C1B C2B C3B . -0.3(2)
C7B C1B C2B C3B . 179.81(14)
C5B N4B C3B C2B . -0.3(2)
C1B C2B C3B N4B . 0.8(2)
C7B N8B C9B O9B . 3.0(3)
C7B N8B C9B C10B . 178.62(14)
C7B N8B C9B C11B . -150.8(8)
N4B C5B C6B C1B . 1.3(3)
C2B C1B C6B C5B . -0.7(2)
C7B C1B C6B C5B . 179.20(15)
C9B N8B C7B C1B . -164.72(15)
C2B C1B C7B N8B . -111.52(17)
C6B C1B C7B N8B . 68.62(19)
C4A C3A C2A C4A 2_665 0.1(2)
C4A C3A C2A C1A . -179.95(13)
O1B C1A C2A C3A . 7.6(2)
O1A C1A C2A C3A . -172.59(14)
O1B C1A C2A C4A 2_665 -172.45(15)
O1A C1A C2A C4A 2_665 7.3(2)
C2A C3A C4A C2A 2_665 -0.1(2)
O9B C9B C10B C10B 2_566 -29.7(2)
N8B C9B C10B C10B 2_566 154.72(16)
C11B C9B C10B C10B 2_566 59.0(14)
O9B C9B C11B C11B 2_566 58.8(19)
N8B C9B C11B C11B 2_566 -145.9(13)
C10B C9B C11B C11B 2_566 -48.4(13)
