#------------------------------------------------------------------------------
#$Date: 2017-03-05 08:33:12 +0200 (Sun, 05 Mar 2017) $
#$Revision: 193931 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/20/2242058.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_2242058
loop_
_publ_author_name
'Cati, Dilovan S.'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Crystal structures of
 N²,N³,N⁵,N⁶-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide
 and
 N²,N³,N⁵,N⁶-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              300
_journal_page_last               305
_journal_paper_doi               10.1107/S205698901700127X
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C32 H28 N10 O4'
_chemical_formula_moiety         'C32 H28 N10 O4'
_chemical_formula_sum            'C32 H28 N10 O4'
_chemical_formula_weight         616.64
_chemical_name_systematic
N²,N³,N⁵,N⁶-Tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 102.306(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8592(6)
_cell_length_b                   10.6511(6)
_cell_length_c                   14.8089(9)
_cell_measurement_reflns_used    7048
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.87
_cell_measurement_theta_min      2.28
_cell_volume                     1519.37(16)
_computing_cell_refinement
;
CELL in IPDS-I (Stoe & Cie, 2000)
;
_computing_data_collection
;
EXPOSE in IPDS-I (Stoe & Cie, 2000)
;
_computing_data_reduction
;
INTEGRATE in IPDS-I (Stoe & Cie, 2000)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015), PLATON (Spek, 2009) and
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '1 circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 1'
_diffrn_measurement_method       'φ rotation'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11450
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.870
_diffrn_reflns_theta_min         2.277
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(MULABS in PLATON; Spek, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0508
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0843P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1338
_reflns_number_gt                1815
_reflns_number_total             2924
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5836sup1.cif
_cod_data_source_block           II
_cod_database_code               2242058
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 -0.03421(18) 0.58335(15) 0.92721(11) 0.0272(4) Uani d 1 . .
N N2 0.22670(19) 0.60099(18) 0.84892(13) 0.0302(4) Uani d 1 . .
H H2N 0.244(3) 0.658(3) 0.898(2) 0.055(8) Uiso d 1 . .
N N4 -0.2443(2) 0.74564(17) 0.91134(12) 0.0299(4) Uani d 1 . .
H H4N -0.182(3) 0.738(2) 0.8753(18) 0.040(7) Uiso d 1 . .
N N5 -0.2772(2) 1.19617(19) 1.02333(13) 0.0430(5) Uani d 1 . .
O O1 0.09946(16) 0.43306(14) 0.78401(10) 0.0357(4) Uani d 1 . .
O O2 -0.29807(17) 0.67310(16) 1.04302(10) 0.0435(5) Uani d 1 . .
C C1 0.0706(2) 0.50299(19) 0.93128(13) 0.0251(5) Uani d 1 . .
C C2 -0.1056(2) 0.58116(19) 0.99495(13) 0.0257(5) Uani d 1 . .
C C3 0.1375(2) 0.5078(2) 0.84783(13) 0.0264(5) Uani d 1 . .
C C4 0.2840(2) 0.6340(2) 0.76899(15) 0.0350(5) Uani d 1 . .
H H4A 0.298850 0.725974 0.769395 0.042 Uiso calc 1 . .
H H4B 0.214362 0.613342 0.712270 0.042 Uiso calc 1 . .
C C5 0.4176(2) 0.5708(2) 0.76382(14) 0.0369(6) Uani d 1 . .
C C6 0.5084(2) 0.6284(3) 0.71674(16) 0.0428(6) Uani d 1 . .
H H6 0.488582 0.710018 0.691424 0.051 Uiso calc 1 . .
C C7 0.6260(3) 0.5674(4) 0.7070(2) 0.0638(9) Uani d 1 . .
H H7 0.695836 0.611527 0.684660 0.077 Uiso calc 1 A 1
N N3A 0.6459(12) 0.4293(17) 0.7318(7) 0.061(3) Uani d 0.58(3) B 1
C C8A 0.5525(14) 0.3778(16) 0.7738(7) 0.057(3) Uani d 0.58(3) B 1
H H8A 0.565436 0.293085 0.793745 0.068 Uiso calc 0.58(3) B 1
C C9A 0.4378(16) 0.4420(15) 0.7897(9) 0.049(2) Uani d 0.58(3) B 1
H H9A 0.372404 0.400153 0.817822 0.059 Uiso calc 0.58(3) B 1
N N3B 0.6817(19) 0.4827(19) 0.7509(12) 0.055(4) Uani d 0.42(3) B 2
C C8B 0.603(2) 0.429(2) 0.8028(15) 0.061(5) Uani d 0.42(3) B 2
H H8B 0.638613 0.355212 0.835676 0.073 Uiso calc 0.42(3) B 2
C C9B 0.474(2) 0.469(2) 0.8135(13) 0.045(4) Uani d 0.42(3) B 2
H H9B 0.426497 0.427346 0.854273 0.054 Uiso calc 0.42(3) B 2
C C10 -0.2250(2) 0.67050(19) 0.98583(14) 0.0292(5) Uani d 1 . .
C C11 -0.3563(2) 0.8358(2) 0.89116(14) 0.0302(5) Uani d 1 . .
H H11A -0.439256 0.798804 0.908574 0.036 Uiso calc 1 . .
H H11B -0.379534 0.850972 0.823670 0.036 Uiso calc 1 . .
C C12 -0.3255(2) 0.9596(2) 0.93967(13) 0.0280(5) Uani d 1 . .
C C13 -0.4219(2) 1.0556(2) 0.91948(15) 0.0335(5) Uani d 1 . .
H H13 -0.506721 1.042206 0.876122 0.040 Uiso calc 1 . .
C C14 -0.3951(2) 1.1701(2) 0.96208(16) 0.0377(6) Uani d 1 . .
H H14 -0.463442 1.234122 0.947499 0.045 Uiso calc 1 . .
C C15 -0.1850(3) 1.1033(2) 1.04220(17) 0.0462(6) Uani d 1 . .
H H15 -0.100541 1.119381 1.085262 0.055 Uiso calc 1 . .
C C16 -0.2041(2) 0.9855(2) 1.00334(15) 0.0374(6) Uani d 1 . .
H H16 -0.134841 0.922753 1.020004 0.045 Uiso calc 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_site_symmetry_3
_geom_angle
C1 N1 C2 . . 118.66(17)
C3 N2 C4 . . 122.83(19)
C3 N2 H2N . . 120.4(17)
C4 N2 H2N . . 115.9(17)
C10 N4 C11 . . 122.25(19)
C10 N4 H4N . . 116.1(16)
C11 N4 H4N . . 121.6(16)
C15 N5 C14 . . 116.3(2)
N1 C1 C2 . 3_567 120.44(19)
N1 C1 C3 . . 114.06(17)
C2 C1 C3 3_567 . 125.39(18)
N1 C2 C1 . 3_567 120.89(19)
N1 C2 C10 . . 116.66(17)
C1 C2 C10 3_567 . 122.44(18)
O1 C3 N2 . . 125.93(19)
O1 C3 C1 . . 119.20(19)
N2 C3 C1 . . 114.69(18)
N2 C4 C5 . . 115.50(18)
N2 C4 H4A . . 108.4
C5 C4 H4A . . 108.4
N2 C4 H4B . . 108.4
C5 C4 H4B . . 108.4
H4A C4 H4B . . 107.5
C9B C5 C6 . . 113.0(8)
C6 C5 C9A . . 119.4(6)
C9B C5 C4 . . 126.4(8)
C6 C5 C4 . . 119.7(2)
C9A C5 C4 . . 119.6(6)
C7 C6 C5 . . 119.7(3)
C7 C6 H6 . . 120.1
C5 C6 H6 . . 120.1
N3B C7 C6 . . 128.0(6)
C6 C7 N3A . . 120.4(5)
C6 C7 H7 . . 119.8
N3A C7 H7 . . 119.8
C8A N3A C7 . . 116.4(7)
N3A C8A C9A . . 123.1(10)
N3A C8A H8A . . 118.4
C9A C8A H8A . . 118.4
C8A C9A C5 . . 120.1(12)
C8A C9A H9A . . 120.0
C5 C9A H9A . . 120.0
C7 N3B C8B . . 112.7(11)
N3B C8B C9B . . 126.5(12)
N3B C8B H8B . . 116.7
C9B C8B H8B . . 116.7
C5 C9B C8B . . 117.8(13)
C5 C9B H9B . . 121.1
C8B C9B H9B . . 121.1
O2 C10 N4 . . 123.6(2)
O2 C10 C2 . . 121.30(18)
N4 C10 C2 . . 115.08(19)
N4 C11 C12 . . 114.61(17)
N4 C11 H11A . . 108.6
C12 C11 H11A . . 108.6
N4 C11 H11B . . 108.6
C12 C11 H11B . . 108.6
H11A C11 H11B . . 107.6
C16 C12 C13 . . 117.0(2)
C16 C12 C11 . . 123.95(19)
C13 C12 C11 . . 119.04(18)
C14 C13 C12 . . 120.0(2)
C14 C13 H13 . . 120.0
C12 C13 H13 . . 120.0
N5 C14 C13 . . 123.2(2)
N5 C14 H14 . . 118.4
C13 C14 H14 . . 118.4
N5 C15 C16 . . 124.2(2)
N5 C15 H15 . . 117.9
C16 C15 H15 . . 117.9
C15 C16 C12 . . 119.2(2)
C15 C16 H16 . . 120.4
C12 C16 H16 . . 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 C1 . 1.333(3)
N1 C2 . 1.343(3)
N2 C3 . 1.324(3)
N2 C4 . 1.459(3)
N2 H2N . 0.93(3)
N4 C10 . 1.343(3)
N4 C11 . 1.446(3)
N4 H4N . 0.90(3)
N5 C15 . 1.333(3)
N5 C14 . 1.342(3)
O1 C3 . 1.232(2)
O2 C10 . 1.224(3)
C1 C2 3_567 1.398(3)
C1 C3 . 1.521(3)
C2 C10 . 1.497(3)
C4 C5 . 1.495(3)
C4 H4A . 0.9900
C4 H4B . 0.9900
C5 C9B . 1.360(18)
C5 C6 . 1.389(3)
C5 C9A . 1.427(16)
C6 C7 . 1.363(4)
C6 H6 . 0.9500
C7 N3B . 1.177(12)
C7 N3A . 1.518(17)
C7 H7 . 0.9500
N3A C8A . 1.334(12)
C8A C9A . 1.384(16)
C8A H8A . 0.9500
C9A H9A . 0.9500
N3B C8B . 1.336(16)
C8B C9B . 1.38(2)
C8B H8B . 0.9500
C9B H9B . 0.9500
C11 C12 . 1.502(3)
C11 H11A . 0.9900
C11 H11B . 0.9900
C12 C16 . 1.384(3)
C12 C13 . 1.385(3)
C13 C14 . 1.373(3)
C13 H13 . 0.9500
C14 H14 . 0.9500
C15 C16 . 1.376(3)
C15 H15 . 0.9500
C16 H16 . 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
C9A H9A O2 3_567 0.95 2.46 3.316(15) 150
'[C9B' H9B O2] 3_567 0.95 2.43 3.375(18) 178
N2 H2N N5 3_577 0.93(3) 1.93(3) 2.845(3) 167(2)
N4 H4N N3A 2_556 0.90(3) 2.65(3) 3.184(13) 119(2)
C6 H6 O1 2_556 0.95 2.58 3.414(3) 146
C11 H11B O1 2_456 0.99 2.56 3.301(2) 132
C14 H14 O2 3_477 0.95 2.58 3.442(3) 151
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
C2 N1 C1 C2 . 3_567 -0.4(3)
C2 N1 C1 C3 . . 176.06(18)
C1 N1 C2 C1 . 3_567 0.4(3)
C1 N1 C2 C10 . . -178.23(17)
C4 N2 C3 O1 . . 5.4(3)
C4 N2 C3 C1 . . -169.63(18)
N1 C1 C3 O1 . . -95.4(2)
C2 C1 C3 O1 3_567 . 80.8(3)
N1 C1 C3 N2 . . 80.0(2)
C2 C1 C3 N2 3_567 . -103.8(2)
C3 N2 C4 C5 . . -91.4(2)
N2 C4 C5 C9B . . 14.7(13)
N2 C4 C5 C6 . . -153.7(2)
N2 C4 C5 C9A . . 39.5(7)
C9B C5 C6 C7 . . 14.2(11)
C9A C5 C6 C7 . . -9.1(7)
C4 C5 C6 C7 . . -175.9(2)
C5 C6 C7 N3B . . -19.6(17)
C5 C6 C7 N3A . . 11.0(7)
C6 C7 N3A C8A . . -8.4(9)
C7 N3A C8A C9A . . 4.0(11)
N3A C8A C9A C5 . . -2.3(11)
C6 C5 C9A C8A . . 4.6(9)
C4 C5 C9A C8A . . 171.5(5)
C6 C7 N3B C8B . . 13.7(16)
C7 N3B C8B C9B . . -5.4(18)
C6 C5 C9B C8B . . -7.3(13)
C4 C5 C9B C8B . . -176.3(10)
N3B C8B C9B C5 . . 3.0(19)
C11 N4 C10 O2 . . -1.2(3)
C11 N4 C10 C2 . . 178.84(18)
N1 C2 C10 O2 . . 178.2(2)
C1 C2 C10 O2 3_567 . -0.4(3)
N1 C2 C10 N4 . . -1.8(3)
C1 C2 C10 N4 3_567 . 179.59(19)
C10 N4 C11 C12 . . 84.7(3)
N4 C11 C12 C16 . . -3.9(3)
N4 C11 C12 C13 . . 175.06(19)
C16 C12 C13 C14 . . -0.1(3)
C11 C12 C13 C14 . . -179.1(2)
C15 N5 C14 C13 . . -0.5(4)
C12 C13 C14 N5 . . 0.6(4)
C14 N5 C15 C16 . . -0.1(4)
N5 C15 C16 C12 . . 0.6(4)
C13 C12 C16 C15 . . -0.5(3)
C11 C12 C16 C15 . . 178.5(2)

_cod_database_fobs_code 2242058
