#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/59/2205958.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_2205958
loop_
_publ_author_name
'Jun Lin'
'Hao Lin'
'Jing-Wen Chen'
'Zi-Jian Guo'
_publ_section_title
;
 Bis[N,N'-o-phenylenebis(pyridine-2,6-dicarboxamide)]
 dimethylformamide solvate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1592
_journal_page_last               o1594
_journal_paper_doi               10.1107/S1600536805013322
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C26 H18 N6 O4,C6 H14 N2 O2'
_chemical_formula_moiety         'C26 H18 N6 O4,C6 H14 N2 O2'
_chemical_formula_sum            'C29 H25 N7 O5'
_chemical_formula_weight         551.06
_chemical_name_systematic
;3,10,18,25,31,32-hexaazapentacyclo[25.3.1.1^12,16^.0^4,9^.0^19,24^]dotriconta-
1(30),4,6,8,12,14,16(32),19,21,23,27(31),28-dodecaene-2,11,17,26-tetrone
dimethylformamide
 solvate
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2331(17)
_cell_length_b                   15.3467(14)
_cell_length_c                   9.5134(9)
_cell_measurement_reflns_used    1146
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.716
_cell_measurement_theta_min      2.415
_cell_volume                     2662.0(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0580
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            13689
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0411P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0977
_reflns_number_gt                1708
_reflns_number_total             2725
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6173.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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      Pnma
_cod_database_code               2205958
_cod_database_fobs_code          2205958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.54669(8) 0.08730(9) 0.92046(16) 0.0410(4) Uani d . 1 . . N
N2 0.58758(8) 0.15760(10) 1.16484(17) 0.0442(4) Uani d . 1 . . N
H2 0.5506 0.1720 1.1137 0.053 Uiso calc R 1 . . H
N3 0.42769(8) 0.15908(10) 0.80243(16) 0.0445(4) Uani d . 1 . . N
H3 0.4470 0.1729 0.8819 0.053 Uiso calc R 1 . . H
C1 0.60768(10) 0.05629(12) 0.9783(2) 0.0429(5) Uani d . 1 . . C
C2 0.65301(12) -0.00290(13) 0.9111(3) 0.0604(6) Uani d . 1 . . C
H2A 0.6954 -0.0234 0.9545 0.073 Uiso calc R 1 . . H
C3 0.63391(12) -0.03071(13) 0.7786(3) 0.0588(6) Uani d . 1 . . C
H3A 0.6642 -0.0689 0.7298 0.071 Uiso calc R 1 . . H
C4 0.56992(11) -0.00187(13) 0.7189(2) 0.0544(6) Uani d . 1 . . C
H4 0.5549 -0.0218 0.6311 0.065 Uiso calc R 1 . . H
C5 0.52826(11) 0.05787(12) 0.7934(2) 0.0465(5) Uani d . 1 . . C
C6 0.63045(10) 0.09256(12) 1.1182(2) 0.0466(5) Uani d . 1 . . C
C7 0.59839(9) 0.20437(13) 1.2912(2) 0.0452(5) Uani d . 1 . . C
C8 0.60752(12) 0.15994(15) 1.4162(2) 0.0587(6) Uani d . 1 . . C
H8 0.6061 0.0994 1.4171 0.070 Uiso calc R 1 . . H
C9 0.61879(12) 0.20520(15) 1.5396(2) 0.0631(6) Uani d . 1 . . C
H9 0.6264 0.1750 1.6231 0.076 Uiso calc R 1 . . H
C10 0.45964(11) 0.09506(13) 0.7273(2) 0.0457(5) Uani d . 1 . . C
C11 0.36433(10) 0.20495(12) 0.75855(18) 0.0387(4) Uani d . 1 . . C
C12 0.30357(10) 0.16061(14) 0.7160(2) 0.0440(5) Uani d . 1 . . C
H12 0.3032 0.1000 0.7177 0.053 Uiso calc R 1 . . H
C13 0.24318(12) 0.20528(15) 0.6709(2) 0.0604(6) Uani d . 1 . . C
H13 0.2020 0.1750 0.6401 0.073 Uiso calc R 1 . . H
O1 0.68464(8) 0.06567(10) 1.18065(17) 0.0684(5) Uani d . 1 . . O
O2 0.43698(7) 0.06891(8) 0.61431(14) 0.0521(4) Uani d . 1 . . O
C14 0.4081(3) 0.2500 0.3693(6) 0.0477(14) Uani d SP 0.50 A 1 C
H14A 0.4579 0.2500 0.3369 0.072 Uiso d SPR 0.50 A 1 H
H14B 0.3995 0.3011 0.4252 0.072 Uiso d PR 0.50 A 1 H
C15 0.2811(3) 0.2500 0.2818(7) 0.0529(16) Uani d SP 0.50 A 1 C
H15A 0.2491 0.2500 0.2016 0.079 Uiso d SPR 0.50 A 1 H
H15B 0.2721 0.1989 0.3374 0.079 Uiso d PR 0.50 A 1 H
C16 0.3824(4) 0.2500 0.1172(8) 0.0506(14) Uani d SP 0.50 A 1 C
H16A 0.3494 0.2500 0.0427 0.061 Uiso d SPR 0.50 A 1 H
N4 0.35369(13) 0.2500 0.2380(2) 0.0506(6) Uani d SP 0.50 . . N
O3 0.44841(9) 0.2500 0.08278(19) 0.0460(5) Uani d SP 0.50 . . O
C14' 0.3146(3) 0.2500 0.3682(6) 0.0479(15) Uani d SP 0.50 A 2 C
H14C 0.3491 0.2500 0.4443 0.072 Uiso d SPR 0.50 A 2 H
H14D 0.2843 0.3011 0.3740 0.072 Uiso d PR 0.50 A 2 H
C15' 0.2957(3) 0.2500 0.1085(6) 0.0564(16) Uani d SP 0.50 A 2 C
H15C 0.3218 0.2500 0.0209 0.085 Uiso d SPR 0.50 A 2 H
H15D 0.2654 0.1989 0.1140 0.085 Uiso d PR 0.50 A 2 H
C16' 0.4189(4) 0.2500 0.2000(7) 0.0490(14) Uani d SP 0.50 A 2 C
H16B 0.4521 0.2500 0.2742 0.059 Uiso d SPR 0.50 A 2 H
N4' 0.35369(13) 0.2500 0.2380(2) 0.0506(6) Uani d SP 0.50 A 2 N
O3' 0.44841(9) 0.2500 0.08278(19) 0.0460(5) Uani d SP 0.50 A 2 O
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
_geom_angle_publ_flag
C1 N1 C5 . . 117.69(16) yes
C6 N2 C7 . . 125.22(16) yes
C6 N2 H2 . . 117.4 ?
C7 N2 H2 . . 117.4 ?
C10 N3 C11 . . 123.97(16) yes
C10 N3 H3 . . 118.0 ?
C11 N3 H3 . . 118.0 ?
N1 C1 C2 . . 122.9(2) ?
N1 C1 C6 . . 117.74(16) ?
C2 C1 C6 . . 119.18(19) ?
C3 C2 C1 . . 118.4(2) ?
C3 C2 H2A . . 120.8 ?
C1 C2 H2A . . 120.8 ?
C4 C3 C2 . . 119.67(19) ?
C4 C3 H3A . . 120.2 ?
C2 C3 H3A . . 120.2 ?
C3 C4 C5 . . 117.9(2) ?
C3 C4 H4 . . 121.0 ?
C5 C4 H4 . . 121.0 ?
N1 C5 C4 . . 123.35(19) ?
N1 C5 C10 . . 117.24(16) ?
C4 C5 C10 . . 119.37(18) ?
O1 C6 N2 . . 124.1(2) yes
O1 C6 C1 . . 121.88(18) yes
N2 C6 C1 . . 114.03(17) ?
C8 C7 C7 . 7_565 119.61(13) ?
C8 C7 N2 . . 119.88(18) ?
C7 C7 N2 7_565 . 120.50(10) ?
C9 C8 C7 . . 120.1(2) ?
C9 C8 H8 . . 119.9 ?
C7 C8 H8 . . 119.9 ?
C9 C9 C8 7_565 . 120.23(13) ?
C9 C9 H9 7_565 . 119.9 ?
C8 C9 H9 . . 119.9 ?
O2 C10 N3 . . 124.14(19) yes
O2 C10 C5 . . 121.51(17) yes
N3 C10 C5 . . 114.34(17) ?
C12 C11 C11 . 7_565 119.98(11) ?
C12 C11 N3 . . 120.20(17) ?
C11 C11 N3 7_565 . 119.81(10) ?
C11 C12 C13 . . 119.89(19) ?
C11 C12 H12 . . 120.1 ?
C13 C12 H12 . . 120.1 ?
C12 C13 C13 . 7_565 120.12(12) ?
C12 C13 H13 . . 119.9 ?
C13 C13 H13 7_565 . 119.9 ?
N4 C14 H14A . . 109.7 ?
N4 C14 H14B . . 109.4 ?
H14A C14 H14B . . 109.5 ?
H14A C14 H14C . . 165.2 ?
H14B C14 H16B . . 121.5 ?
H14C C14 H16B . . 165.1 ?
N4 C15 H15A . . 110.0 ?
N4 C15 H15B . . 109.2 ?
H15A C15 H15B . . 109.5 ?
N4 C15 H14D . . 100.1 ?
H15A C15 H14D . . 128.4 ?
H15B C15 H14D . . 98.1 ?
O3 C16 N4 . . 129.7(7) ?
O3 C16 H16A . . 115.1 ?
N4 C16 H16A . . 115.1 ?
O3 C16 H15C . . 125.1 ?
N4 C16 H15C . . 105.2 ?
C16' N4 C15 . . 179.5(5) ?
C16 N4 C15 . . 132.0(5) ?
C16' N4 C14' . . 136.9(5) ?
C16 N4 C14' . . 174.6(5) ?
C16 N4 C14 . . 117.0(4) ?
C15 N4 C14 . . 111.0(4) ?
C16' N4 C15' . . 113.7(5) ?
C14' N4 C15' . . 109.4(4) ?
C14 N4 C15' . . 177.8(3) ?
N4 C14' H15B . . 96.7 ?
N4 C14' H14C . . 109.0 ?
H15B C14' H14C . . 129.8 ?
N4 C14' H14D . . 109.7 ?
H15B C14' H14D . . 100.7 ?
H14C C14' H14D . . 109.5 ?
H15A C15' H16A . . 166.3 ?
N4 C15' H15C . . 109.5 ?
H15A C15' H15C . . 166.0 ?
N4 C15' H15D . . 109.4 ?
H15C C15' H15D . . 109.5 ?
O3 C16' N4 . . 132.7(7) ?
O3 C16' H14A . . 125.6 ?
N4 C16' H14A . . 101.7 ?
O3 C16' H16B . . 113.7 ?
N4 C16' H16B . . 113.7 ?
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
N1 C1 . 1.329(2) yes
N1 C5 . 1.333(2) yes
N2 C6 . 1.343(2) yes
N2 C7 . 1.414(2) yes
N2 H2 . 0.8600 ?
N3 C10 . 1.347(2) yes
N3 C11 . 1.416(2) yes
N3 H3 . 0.8600 ?
C1 C2 . 1.384(3) ?
C1 C6 . 1.502(3) ?
C2 C3 . 1.375(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.371(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.386(3) ?
C4 H4 . 0.9300 ?
C5 C10 . 1.512(3) ?
C6 O1 . 1.224(2) yes
C7 C8 . 1.380(3) ?
C7 C7 7_565 1.400(4) ?
C8 C9 . 1.380(3) ?
C8 H8 . 0.9300 ?
C9 C9 7_565 1.375(5) ?
C9 H9 . 0.9300 ?
C10 O2 . 1.219(2) yes
C11 C12 . 1.362(2) ?
C11 C11 7_565 1.383(4) ?
C12 C13 . 1.366(3) ?
C12 H12 . 0.9300 ?
C13 C13 7_565 1.373(5) ?
C13 H13 . 0.9300 ?
C14 N4 . 1.595(6) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9601 ?
C14 H14C . 1.2901 ?
C14 H16B . 1.2097 ?
C15 N4 . 1.387(6) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H14D . 1.1782 ?
C16 O3 . 1.247(6) ?
C16 N4 . 1.263(7) ?
C16 H16A . 0.9300 ?
N4 C16' . 1.243(6) ?
N4 C14' . 1.429(5) ?
N4 C15' . 1.624(6) ?
O3 C16' . 1.238(6) ?
C14' H15B . 1.1407 ?
C14' H14C . 0.9600 ?
C14' H14D . 0.9601 ?
C15' H15A . 1.2272 ?
C15' H15C . 0.9600 ?
C15' H15D . 0.9600 ?
C16' H16B . 0.9300 ?
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 H2 O3' 1_556 0.86 2.23 3.010(2) 150 yes
N2 H2 O3 1_556 0.86 2.23 3.010(2) 150 yes
N3 H3 O3' 1_556 0.86 2.25 3.034(2) 152 yes
N3 H3 O3 1_556 0.86 2.25 3.034(2) 152 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_1
_geom_torsion_site_symmetry_4
_geom_torsion
C5 N1 C1 C2 . . 1.6(3)
C5 N1 C1 C6 . . 177.10(16)
N1 C1 C2 C3 . . 0.0(3)
C6 C1 C2 C3 . . -175.45(19)
C1 C2 C3 C4 . . -2.2(3)
C2 C3 C4 C5 . . 2.8(3)
C1 N1 C5 C4 . . -1.0(3)
C1 N1 C5 C10 . . -178.70(16)
C3 C4 C5 N1 . . -1.2(3)
C3 C4 C5 C10 . . 176.50(19)
C7 N2 C6 O1 . . 0.1(3)
C7 N2 C6 C1 . . -178.08(16)
N1 C1 C6 O1 . . 177.72(17)
C2 C1 C6 O1 . . -6.6(3)
N1 C1 C6 N2 . . -4.1(2)
C2 C1 C6 N2 . . 171.61(17)
C6 N2 C7 C8 . . -51.6(3)
C6 N2 C7 C7 . 7_565 129.79(15)
C7 C7 C8 C9 7_565 . -2.0(3)
N2 C7 C8 C9 . . 179.37(19)
C7 C8 C9 C9 . 7_565 2.0(3)
C11 N3 C10 O2 . . -1.0(3)
C11 N3 C10 C5 . . 177.99(16)
N1 C5 C10 O2 . . -176.57(18)
C4 C5 C10 O2 . . 5.6(3)
N1 C5 C10 N3 . . 4.4(2)
C4 C5 C10 N3 . . -173.37(18)
C10 N3 C11 C12 . . 51.0(3)
C10 N3 C11 C11 . 7_565 -128.84(15)
C11 C11 C12 C13 7_565 . 1.2(2)
N3 C11 C12 C13 . . -178.56(18)
C11 C12 C13 C13 . 7_565 -1.2(2)
O3 C16 N4 C15 . . 180.0
O3 C16 N4 C15' . . 180.0
C14 N4 C16' O3 . . 180.0
