#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/54/2205470.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_2205470
loop_
_publ_author_name
'Cai-Feng Ding'
'Mei Zhu'
'Xue-Mei Li'
'Shu-Sheng Zhang'
'Hong Xu'
'Ping-Kai Ouyang'
_publ_section_title
;
 1,6-Bis(pyridine-4-carboxamido)hexane
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1103
_journal_page_last               o1104
_journal_paper_doi               10.1107/S1600536805008688
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H22 N4 O2'
_chemical_formula_moiety         'C18 H22 N4 O2'
_chemical_formula_sum            'C18 H22 N4 O2'
_chemical_formula_weight         326.40
_chemical_name_systematic
;
1,6-Bis(pyridine-4-carboxamido)hexane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.067(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0940(9)
_cell_length_b                   5.2911(10)
_cell_length_c                   30.759(6)
_cell_measurement_reflns_used    1592
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.6
_cell_volume                     828.9(3)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Siemens SMART 1000 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  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            4366
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.32
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0413
_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)+(0.0567P)²+0.1501P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1131
_reflns_number_gt                1363
_reflns_number_total             1616
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6474.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2205470
_cod_database_fobs_code          2205470
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_type_symbol
O1 0.19333(19) 0.6683(2) 0.10242(4) 0.0556(4) Uani d . 1 O
N1 -0.2033(3) 1.1864(3) 0.22080(4) 0.0516(4) Uani d . 1 N
N2 -0.2330(2) 0.5678(2) 0.09456(4) 0.0415(3) Uani d . 1 N
H2A -0.3908 0.5915 0.1031 0.050 Uiso calc R 1 H
C1 -0.3122(3) 0.8210(3) 0.17818(5) 0.0429(4) Uani d . 1 C
H1B -0.4231 0.6835 0.1736 0.052 Uiso calc R 1 H
C2 -0.3530(3) 0.9858(3) 0.21231(5) 0.0484(4) Uani d . 1 C
H2B -0.4935 0.9544 0.2304 0.058 Uiso calc R 1 H
C3 -0.0032(3) 1.2257(3) 0.19426(5) 0.0486(4) Uani d . 1 C
H3A 0.1037 1.3653 0.1995 0.058 Uiso calc R 1 H
C4 0.0546(3) 1.0715(3) 0.15957(5) 0.0426(4) Uani d . 1 C
H4A 0.1977 1.1065 0.1422 0.051 Uiso calc R 1 H
C5 -0.1032(3) 0.8642(3) 0.15094(4) 0.0362(3) Uani d . 1 C
C6 -0.0357(3) 0.6926(3) 0.11385(5) 0.0384(3) Uani d . 1 C
C7 -0.1848(3) 0.3914(3) 0.05915(5) 0.0434(4) Uani d . 1 C
H7A -0.0487 0.2733 0.0682 0.052 Uiso calc R 1 H
H7B -0.1217 0.4844 0.0343 0.052 Uiso calc R 1 H
C8 -0.4277(3) 0.2463(3) 0.04592(5) 0.0418(4) Uani d . 1 C
H8A -0.5662 0.3644 0.0381 0.050 Uiso calc R 1 H
H8B -0.4865 0.1473 0.0704 0.050 Uiso calc R 1 H
C9 -0.3782(3) 0.0712(3) 0.00769(5) 0.0418(4) Uani d . 1 C
H9A -0.3121 0.1701 -0.0163 0.063 Uiso calc R 1 H
H9B -0.2435 -0.0500 0.0160 0.063 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0324(6) 0.0724(8) 0.0623(7) -0.0019(5) 0.0081(5) -0.0239(6)
N1 0.0567(8) 0.0539(8) 0.0443(7) 0.0079(7) 0.0030(6) -0.0083(6)
N2 0.0312(6) 0.0504(7) 0.0431(7) 0.0007(5) 0.0046(5) -0.0122(6)
C1 0.0391(8) 0.0463(9) 0.0435(8) -0.0009(6) 0.0034(6) -0.0006(7)
C2 0.0457(8) 0.0603(10) 0.0397(8) 0.0074(8) 0.0086(7) 0.0005(7)
C3 0.0506(9) 0.0445(9) 0.0506(9) -0.0017(7) -0.0018(7) -0.0079(7)
C4 0.0389(8) 0.0473(9) 0.0416(8) -0.0006(6) 0.0034(6) -0.0016(7)
C5 0.0325(7) 0.0415(8) 0.0346(7) 0.0049(6) 0.0001(5) -0.0006(6)
C6 0.0317(7) 0.0431(8) 0.0404(8) 0.0015(6) 0.0034(6) -0.0034(6)
C7 0.0365(8) 0.0514(9) 0.0427(8) -0.0003(7) 0.0062(6) -0.0114(7)
C8 0.0351(7) 0.0454(8) 0.0452(8) -0.0001(6) 0.0049(6) -0.0081(7)
C9 0.0360(7) 0.0435(8) 0.0461(8) -0.0001(6) 0.0054(6) -0.0088(7)
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
C2 N1 C3 . 116.49(13) ?
C6 N2 C7 . 120.91(11) yes
C6 N2 H2A . 119.5 ?
C7 N2 H2A . 119.5 ?
C2 C1 C5 . 118.85(15) ?
C2 C1 H1B . 120.6 ?
C5 C1 H1B . 120.6 ?
N1 C2 C1 . 123.95(14) ?
N1 C2 H2B . 118.0 ?
C1 C2 H2B . 118.0 ?
N1 C3 C4 . 123.92(15) ?
N1 C3 H3A . 118.0 ?
C4 C3 H3A . 118.0 ?
C3 C4 C5 . 119.07(14) ?
C3 C4 H4A . 120.5 ?
C5 C4 H4A . 120.5 ?
C4 C5 C1 . 117.72(13) ?
C4 C5 C6 . 118.99(12) ?
C1 C5 C6 . 123.25(13) ?
O1 C6 N2 . 122.12(13) yes
O1 C6 C5 . 120.73(13) yes
N2 C6 C5 . 117.14(12) yes
N2 C7 C8 . 112.28(11) ?
N2 C7 H7A . 109.1 ?
C8 C7 H7A . 109.1 ?
N2 C7 H7B . 109.1 ?
C8 C7 H7B . 109.1 ?
H7A C7 H7B . 107.9 ?
C7 C8 C9 . 111.85(12) ?
C7 C8 H8A . 109.2 ?
C9 C8 H8A . 109.2 ?
C7 C8 H8B . 109.2 ?
C9 C8 H8B . 109.2 ?
H8A C8 H8B . 107.9 ?
C9 C9 C8 3_455 113.34(14) ?
C9 C9 H9A 3_455 108.9 ?
C8 C9 H9A . 108.9 ?
C9 C9 H9B 3_455 108.9 ?
C8 C9 H9B . 108.9 ?
H9A C9 H9B . 107.7 ?
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 C6 . 1.2315(16) yes
N1 C2 . 1.330(2) yes
N1 C3 . 1.334(2) yes
N2 C6 . 1.3325(18) yes
N2 C7 . 1.4584(18) yes
N2 H2A . 0.8600 ?
C1 C2 . 1.383(2) ?
C1 C5 . 1.386(2) ?
C1 H1B . 0.9300 ?
C2 H2B . 0.9300 ?
C3 C4 . 1.379(2) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.383(2) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.5030(19) ?
C7 C8 . 1.506(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.5220(19) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C9 3_455 1.520(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
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
_geom_hbond_publ_flag
N2 H2A O1 1_455 0.85 2.16 2.9850(10) 162 yes
C2 H2B N1 2_445 0.93 2.60 3.466(2) 156 yes
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
C3 N1 C2 C1 . -0.1(2)
C5 C1 C2 N1 . 0.2(2)
C2 N1 C3 C4 . -0.3(2)
N1 C3 C4 C5 . 0.7(2)
C3 C4 C5 C1 . -0.5(2)
C3 C4 C5 C6 . -178.40(13)
C2 C1 C5 C4 . 0.1(2)
C2 C1 C5 C6 . 177.91(13)
C7 N2 C6 O1 . 1.1(2)
C7 N2 C6 C5 . -178.15(12)
C4 C5 C6 O1 . 28.6(2)
C1 C5 C6 O1 . -149.21(15)
C4 C5 C6 N2 . -152.18(13)
C1 C5 C6 N2 . 30.1(2)
C6 N2 C7 C8 . 172.60(13)
N2 C7 C8 C9 . 177.54(12)
C7 C8 C9 C9 3_455 -177.83(16)
