#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/76/1557620.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_1557620
loop_
_publ_author_name
'Detert, Heiner'
'Jochem, Matthias'
'Schollmeyer, Dieter'
_publ_section_title
;
 2,5-Bis[(E)-2-phenylethenyl]-3,6-bis(pyridin-2-yl)pyrazine
;
_journal_coeditor_code           BT4090
_journal_issue                   3
_journal_name_full               IUCrData
_journal_page_first              x200372
_journal_paper_doi               10.1107/S2414314620003727
_journal_volume                  5
_journal_year                    2020
_chemical_formula_iupac          'C30 H22 N4'
_chemical_formula_moiety         'C30 H22 N4'
_chemical_formula_sum            'C30 H22 N4'
_chemical_formula_weight         438.51
_chemical_name_systematic
;
2,5-Bis[(E)-2-phenylethenyl]-3,6-bis(pyridin-2-yl)pyrazine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.490(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0953(8)
_cell_length_b                   8.9310(8)
_cell_length_c                   18.219(2)
_cell_measurement_reflns_used    3402
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.54
_cell_volume                     1149.2(2)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 1996)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 1996)
;
_computing_data_reduction
;
X-RED (Stoe & Cie, 1996)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2004 (Burla et al.,  2005)
;
_diffrn_ambient_temperature      193(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.933
_diffrn_reflns_theta_min         2.542
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0434
_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)+(0.0551P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                1622
_reflns_number_total             2718
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            bt4090sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1557620
_cod_database_fobs_code          1557620
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which fp29.ckf  fp29.fcf should always be used as a
source of symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.995
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.56710(15) 0.38847(13) 0.45640(6) 0.0371(3) Uani d 1 . .
C C2 0.65303(18) 0.52229(16) 0.46177(7) 0.0356(3) Uani d 1 . .
C C3 0.58305(19) 0.63537(16) 0.50618(7) 0.0349(3) Uani d 1 . .
C C4 0.82169(19) 0.54154(17) 0.42232(8) 0.0377(3) Uani d 1 . .
H H4 0.898305 0.627307 0.433494 0.045 Uiso calc 1 . .
C C5 0.8747(2) 0.44665(17) 0.37180(8) 0.0394(3) Uani d 1 . .
H H5 0.796135 0.361702 0.361337 0.047 Uiso calc 1 . .
C C6 1.04162(19) 0.45956(17) 0.33065(8) 0.0385(4) Uani d 1 . .
C C7 1.0601(2) 0.3624(2) 0.27172(8) 0.0524(4) Uani d 1 . .
H H7 0.965446 0.288996 0.259487 0.063 Uiso calc 1 . .
C C8 1.2135(3) 0.3716(2) 0.23111(10) 0.0691(6) Uani d 1 . .
H H8 1.223164 0.305063 0.190953 0.083 Uiso calc 1 . .
C C9 1.3524(3) 0.4758(3) 0.24812(10) 0.0697(6) Uani d 1 . .
H H9 1.458129 0.481619 0.219953 0.084 Uiso calc 1 . .
C C10 1.3377(2) 0.5724(2) 0.30648(10) 0.0585(5) Uani d 1 . .
H H10 1.433770 0.644817 0.318544 0.070 Uiso calc 1 . .
C C11 1.1840(2) 0.56400(19) 0.34735(8) 0.0444(4) Uani d 1 . .
H H11 1.175609 0.630726 0.387515 0.053 Uiso calc 1 . .
C C12 0.66436(18) 0.78758(17) 0.51362(8) 0.0364(3) Uani d 1 . .
N N13 0.69586(16) 0.85842(14) 0.45085(7) 0.0415(3) Uani d 1 . .
C C14 0.7551(2) 1.00017(19) 0.45675(10) 0.0487(4) Uani d 1 . .
H H14 0.774730 1.052537 0.412735 0.058 Uiso calc 1 . .
C C15 0.7892(2) 1.0746(2) 0.52227(11) 0.0545(5) Uani d 1 . .
H H15 0.831478 1.175580 0.523436 0.065 Uiso calc 1 . .
C C16 0.7610(2) 1.0003(2) 0.58648(10) 0.0555(5) Uani d 1 . .
H H16 0.786532 1.048282 0.632899 0.067 Uiso calc 1 . .
C C17 0.6949(2) 0.85434(19) 0.58234(9) 0.0467(4) Uani d 1 . .
H H17 0.671004 0.801209 0.625662 0.056 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
C3 N1 C2 3_666 . 118.95(12) ?
N1 C2 C3 . . 119.76(12) ?
N1 C2 C4 . . 117.14(13) ?
C3 C2 C4 . . 123.06(13) ?
N1 C3 C2 3_666 . 121.29(13) ?
N1 C3 C12 3_666 . 115.04(12) ?
C2 C3 C12 . . 123.65(12) ?
C5 C4 C2 . . 124.26(14) ?
C5 C4 H4 . . 117.9 ?
C2 C4 H4 . . 117.9 ?
C4 C5 C6 . . 126.81(14) ?
C4 C5 H5 . . 116.6 ?
C6 C5 H5 . . 116.6 ?
C11 C6 C7 . . 117.79(14) ?
C11 C6 C5 . . 123.22(13) ?
C7 C6 C5 . . 118.99(14) ?
C8 C7 C6 . . 120.94(17) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C9 C8 C7 . . 120.52(17) ?
C9 C8 H8 . . 119.7 ?
C7 C8 H8 . . 119.7 ?
C8 C9 C10 . . 119.56(16) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C11 C10 C9 . . 120.21(17) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C6 . . 120.97(16) ?
C10 C11 H11 . . 119.5 ?
C6 C11 H11 . . 119.5 ?
N13 C12 C17 . . 122.83(15) ?
N13 C12 C3 . . 116.76(13) ?
C17 C12 C3 . . 120.31(14) ?
C14 N13 C12 . . 117.03(14) ?
N13 C14 C15 . . 124.01(16) ?
N13 C14 H14 . . 118.0 ?
C15 C14 H14 . . 118.0 ?
C14 C15 C16 . . 118.66(17) ?
C14 C15 H15 . . 120.7 ?
C16 C15 H15 . . 120.7 ?
C15 C16 C17 . . 118.92(16) ?
C15 C16 H16 . . 120.5 ?
C17 C16 H16 . . 120.5 ?
C16 C17 C12 . . 118.51(16) ?
C16 C17 H17 . . 120.7 ?
C12 C17 H17 . . 120.7 ?
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 C3 3_666 1.3356(17) ?
N1 C2 . 1.3410(18) ?
C2 C3 . 1.4136(19) ?
C2 C4 . 1.4638(19) ?
C3 C12 . 1.478(2) ?
C4 C5 . 1.332(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.4655(19) ?
C5 H5 . 0.9500 ?
C6 C11 . 1.387(2) ?
C6 C7 . 1.396(2) ?
C7 C8 . 1.376(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.369(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.381(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.380(2) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
C12 N13 . 1.3442(18) ?
C12 C17 . 1.385(2) ?
N13 C14 . 1.335(2) ?
C14 C15 . 1.368(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.376(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.385(2) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
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
C3 N1 C2 C3 3_666 . . . -0.4(2) ?
C3 N1 C2 C4 3_666 . . . 177.52(12) ?
N1 C2 C3 N1 . . . 3_666 0.4(2) ?
C4 C2 C3 N1 . . . 3_666 -177.38(12) ?
N1 C2 C3 C12 . . . . -177.97(12) ?
C4 C2 C3 C12 . . . . 4.2(2) ?
N1 C2 C4 C5 . . . . 12.6(2) ?
C3 C2 C4 C5 . . . . -169.56(13) ?
C2 C4 C5 C6 . . . . -179.88(13) ?
C4 C5 C6 C11 . . . . 9.9(2) ?
C4 C5 C6 C7 . . . . -170.21(15) ?
C11 C6 C7 C8 . . . . -0.8(2) ?
C5 C6 C7 C8 . . . . 179.34(15) ?
C6 C7 C8 C9 . . . . 0.5(3) ?
C7 C8 C9 C10 . . . . -0.1(3) ?
C8 C9 C10 C11 . . . . -0.1(3) ?
C9 C10 C11 C6 . . . . -0.2(2) ?
C7 C6 C11 C10 . . . . 0.7(2) ?
C5 C6 C11 C10 . . . . -179.48(14) ?
N1 C3 C12 N13 3_666 . . . -130.40(13) ?
C2 C3 C12 N13 . . . . 48.11(17) ?
N1 C3 C12 C17 3_666 . . . 46.03(17) ?
C2 C3 C12 C17 . . . . -135.47(14) ?
C17 C12 N13 C14 . . . . -1.5(2) ?
C3 C12 N13 C14 . . . . 174.83(12) ?
C12 N13 C14 C15 . . . . 1.6(2) ?
N13 C14 C15 C16 . . . . -0.1(2) ?
C14 C15 C16 C17 . . . . -1.6(2) ?
C15 C16 C17 C12 . . . . 1.7(2) ?
N13 C12 C17 C16 . . . . -0.1(2) ?
C3 C12 C17 C16 . . . . -176.32(13) ?
