#------------------------------------------------------------------------------
#$Date: 2020-02-19 07:55:49 +0200 (Wed, 19 Feb 2020) $
#$Revision: 248286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/32/2243295.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_2243295
loop_
_publ_author_name
'Tesouro Vallina, Ana'
'Stoeckli-Evans, Helen'
_publ_section_title
;
 Crystal structures and Hirshfeld surface analyses of two new
 tetrakis-substituted pyrazines and a degredation product
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              404
_journal_page_last               409
_journal_paper_doi               10.1107/S2056989020002133
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C36 H40 N6'
_chemical_formula_moiety         'C36 H40 N6'
_chemical_formula_sum            'C36 H40 N6'
_chemical_formula_weight         556.74
_chemical_name_systematic
;
N,N',N'',N'''-[Pyrazine-2,3,5,6\
tetrayltetrakis(methylene)]tetrakis(N-methylaniline)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                85.774(10)
_cell_angle_beta                 73.468(11)
_cell_angle_gamma                82.467(11)
_cell_formula_units_Z            1
_cell_length_a                   8.6753(10)
_cell_length_b                   8.9160(11)
_cell_length_c                   10.0631(10)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.6
_cell_measurement_theta_min      12.5
_cell_volume                     739.21(15)
_computing_cell_refinement
;
STADI4 (Stoe & Cie, 1997)
;
_computing_data_collection
;
STADI4 (Stoe & Cie, 1997)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 1997)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015), PLATON (Spek, 2020)
and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation counter'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Stoe--Siemens AED2, 4-circle'
_diffrn_measurement_method       'ω/\2q scans'
_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  0.0313
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5354
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.477
_diffrn_reflns_theta_min         2.113
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            pale-greenish-yellow
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             298
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.145
_refine_ls_extinction_coef       0.026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
(SHELXL2018/3; Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0493
_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)+(0.0254P)²+0.2540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                1913
_reflns_number_total             2741
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            xi2023sup1.cif
_cod_data_source_block           II
_cod_database_code               2243295
_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, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.46201(19) 0.59971(18) 0.89913(16) 0.0393(4) Uani d 1 . .
N N2 0.5739(2) 0.31235(19) 0.66461(17) 0.0454(4) Uani d 1 . .
N N3 0.2493(2) 0.85914(19) 0.95305(17) 0.0481(5) Uani d 1 . .
C C1 0.5585(2) 0.4702(2) 0.86471(19) 0.0366(5) Uani d 1 . .
C C2 0.4027(2) 0.6301(2) 1.0334(2) 0.0378(5) Uani d 1 . .
C C3 0.6246(2) 0.4442(2) 0.7110(2) 0.0437(5) Uani d 1 . .
H H3A 0.590818 0.533444 0.660508 0.052 Uiso calc 1 . .
H H3B 0.741879 0.433034 0.687257 0.052 Uiso calc 1 . .
C C4 0.4248(3) 0.3268(2) 0.63526(19) 0.0429(5) Uani d 1 . .
C C5 0.3070(3) 0.4493(3) 0.6795(2) 0.0502(6) Uani d 1 . .
H H5 0.328637 0.524582 0.728604 0.060 Uiso calc 1 . .
C C6 0.1604(3) 0.4603(3) 0.6515(2) 0.0619(7) Uani d 1 . .
H H6 0.083983 0.542794 0.682224 0.074 Uiso calc 1 . .
C C7 0.1237(3) 0.3508(3) 0.5785(3) 0.0674(7) Uani d 1 . .
H H7 0.024139 0.359185 0.559288 0.081 Uiso calc 1 . .
C C8 0.2367(3) 0.2306(3) 0.5354(3) 0.0661(7) Uani d 1 . .
H H8 0.212966 0.155880 0.486985 0.079 Uiso calc 1 . .
C C9 0.3863(3) 0.2167(2) 0.5618(2) 0.0549(6) Uani d 1 . .
H H9 0.461601 0.133665 0.530481 0.066 Uiso calc 1 . .
C C10 0.7008(3) 0.2013(3) 0.5894(3) 0.0645(7) Uani d 1 . .
H H10A 0.799406 0.208832 0.612583 0.097 Uiso calc 1 . .
H H10B 0.717471 0.220396 0.491434 0.097 Uiso calc 1 . .
H H10C 0.669345 0.101522 0.614401 0.097 Uiso calc 1 . .
C C11 0.2938(3) 0.7782(2) 1.0686(2) 0.0488(6) Uani d 1 . .
H H11A 0.195686 0.756971 1.138934 0.059 Uiso calc 1 . .
H H11B 0.348395 0.843600 1.108603 0.059 Uiso calc 1 . .
C C12 0.1177(2) 0.8292(2) 0.9122(2) 0.0431(5) Uani d 1 . .
C C13 0.0121(3) 0.7258(3) 0.9845(2) 0.0586(6) Uani d 1 . .
H H13 0.032849 0.671020 1.061037 0.070 Uiso calc 1 . .
C C14 -0.1220(3) 0.7040(3) 0.9440(3) 0.0697(7) Uani d 1 . .
H H14 -0.191144 0.635993 0.994996 0.084 Uiso calc 1 . .
C C15 -0.1562(3) 0.7802(3) 0.8302(3) 0.0690(7) Uani d 1 . .
H H15 -0.247073 0.765006 0.803564 0.083 Uiso calc 1 . .
C C16 -0.0517(3) 0.8795(3) 0.7571(3) 0.0643(7) Uani d 1 . .
H H16 -0.072129 0.931190 0.679059 0.077 Uiso calc 1 . .
C C17 0.0822(3) 0.9052(2) 0.7956(2) 0.0516(6) Uani d 1 . .
H H17 0.149960 0.973716 0.743706 0.062 Uiso calc 1 . .
C C18 0.3667(3) 0.9499(3) 0.8637(3) 0.0633(7) Uani d 1 . .
H H18A 0.407036 0.906772 0.774033 0.095 Uiso calc 1 . .
H H18B 0.454775 0.952213 0.903352 0.095 Uiso calc 1 . .
H H18C 0.316286 1.051147 0.854497 0.095 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'
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
C2 N1 C1 . . 118.46(16) ?
C4 N2 C10 . . 117.64(17) ?
C4 N2 C3 . . 118.71(16) ?
C10 N2 C3 . . 117.17(18) ?
C12 N3 C11 . . 122.00(18) ?
C12 N3 C18 . . 120.07(17) ?
C11 N3 C18 . . 116.70(18) ?
N1 C1 C2 . 2_667 120.79(16) ?
N1 C1 C3 . . 115.85(16) ?
C2 C1 C3 2_667 . 123.33(17) ?
N1 C2 C1 . 2_667 120.74(17) ?
N1 C2 C11 . . 117.03(17) ?
C1 C2 C11 2_667 . 122.23(17) ?
N2 C3 C1 . . 114.84(17) ?
N2 C3 H3A . . 108.6 ?
C1 C3 H3A . . 108.6 ?
N2 C3 H3B . . 108.6 ?
C1 C3 H3B . . 108.6 ?
H3A C3 H3B . . 107.5 ?
N3 C11 C2 . . 115.02(17) ?
N3 C11 H11A . . 108.5 ?
C2 C11 H11A . . 108.5 ?
N3 C11 H11B . . 108.5 ?
C2 C11 H11B . . 108.5 ?
H11A C11 H11B . . 107.5 ?
N2 C4 C9 . . 120.81(19) ?
N2 C4 C5 . . 121.91(19) ?
C9 C4 C5 . . 117.3(2) ?
C6 C5 C4 . . 121.1(2) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 121.2(2) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C8 C7 C6 . . 118.4(2) ?
C8 C7 H7 . . 120.8 ?
C6 C7 H7 . . 120.8 ?
C7 C8 C9 . . 121.7(2) ?
C7 C8 H8 . . 119.2 ?
C9 C8 H8 . . 119.2 ?
C8 C9 C4 . . 120.4(2) ?
C8 C9 H9 . . 119.8 ?
C4 C9 H9 . . 119.8 ?
N3 C12 C13 . . 122.77(19) ?
N3 C12 C17 . . 120.5(2) ?
C13 C12 C17 . . 116.7(2) ?
C14 C13 C12 . . 121.0(2) ?
C14 C13 H13 . . 119.5 ?
C12 C13 H13 . . 119.5 ?
C15 C14 C13 . . 121.6(2) ?
C15 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
C16 C15 C14 . . 117.7(2) ?
C16 C15 H15 . . 121.1 ?
C14 C15 H15 . . 121.1 ?
C15 C16 C17 . . 122.1(2) ?
C15 C16 H16 . . 119.0 ?
C17 C16 H16 . . 119.0 ?
C16 C17 C12 . . 120.8(2) ?
C16 C17 H17 . . 119.6 ?
C12 C17 H17 . . 119.6 ?
N3 C18 H18A . . 109.5 ?
N3 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N3 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N2 C10 H10A . . 109.5 ?
N2 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N2 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
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 C2 . 1.336(2) ?
N1 C1 . 1.339(2) ?
N2 C4 . 1.395(3) ?
N2 C10 . 1.454(3) ?
N2 C3 . 1.459(3) ?
N3 C12 . 1.382(3) ?
N3 C11 . 1.442(2) ?
N3 C18 . 1.445(3) ?
C1 C2 2_667 1.395(3) ?
C1 C3 . 1.512(3) ?
C2 C11 . 1.521(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C9 . 1.398(3) ?
C4 C5 . 1.398(3) ?
C5 C6 . 1.369(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.359(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.386(3) ?
C8 H8 . 0.9300 ?
C9 H9 . 0.9300 ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.400(3) ?
C12 C17 . 1.401(3) ?
C13 C14 . 1.378(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.374(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.371(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.375(3) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
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
C5 H5 N1 . 0.93 2.50 3.331(3) 149
C6 H6 Cg3 . 0.93 2.99 3.804(3) 147
C3 H3A C<i>g</i>2 2_666 0.97 2.83 3.561(2) 133
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C2 . . . 2_667 -0.5(3) ?
C2 N1 C1 C3 . . . . -178.66(17) ?
C1 N1 C2 C1 . . . 2_667 0.5(3) ?
C1 N1 C2 C11 . . . . 179.92(17) ?
C4 N2 C3 C1 . . . . 83.8(2) ?
C10 N2 C3 C1 . . . . -125.0(2) ?
N1 C1 C3 N2 . . . . -117.34(19) ?
C2 C1 C3 N2 2_667 . . . 64.5(2) ?
C12 N3 C11 C2 . . . . 86.2(2) ?
C18 N3 C11 C2 . . . . -81.1(2) ?
N1 C2 C11 N3 . . . . 8.2(3) ?
C1 C2 C11 N3 2_667 . . . -172.42(18) ?
C10 N2 C4 C9 . . . . 14.5(3) ?
C3 N2 C4 C9 . . . . 165.50(19) ?
C10 N2 C4 C5 . . . . -166.6(2) ?
C3 N2 C4 C5 . . . . -15.6(3) ?
N2 C4 C5 C6 . . . . -178.9(2) ?
C9 C4 C5 C6 . . . . 0.0(3) ?
C4 C5 C6 C7 . . . . -0.1(4) ?
C5 C6 C7 C8 . . . . 0.4(4) ?
C6 C7 C8 C9 . . . . -0.6(4) ?
C7 C8 C9 C4 . . . . 0.5(4) ?
N2 C4 C9 C8 . . . . 178.8(2) ?
C5 C4 C9 C8 . . . . -0.2(3) ?
C11 N3 C12 C13 . . . . 4.2(3) ?
C18 N3 C12 C13 . . . . 171.1(2) ?
C11 N3 C12 C17 . . . . -177.13(19) ?
C18 N3 C12 C17 . . . . -10.2(3) ?
N3 C12 C13 C14 . . . . 177.1(2) ?
C17 C12 C13 C14 . . . . -1.7(3) ?
C12 C13 C14 C15 . . . . 1.2(4) ?
C13 C14 C15 C16 . . . . 0.1(4) ?
C14 C15 C16 C17 . . . . -0.8(4) ?
C15 C16 C17 C12 . . . . 0.3(4) ?
N3 C12 C17 C16 . . . . -177.8(2) ?
C13 C12 C17 C16 . . . . 1.0(3) ?

_cod_database_fobs_code 2243295
