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#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516575.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4516575
loop_
_publ_author_name
'Patyk, Ewa'
'Podsiadło, Marcin'
'Katrusiak, Andrzej'
_publ_section_title
;
 Discrete CH···N Bonded Patterns Modified by
 Temperature and Pressure in Four Pyrazine Polymorphs
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5670
_journal_paper_doi               10.1021/acs.cgd.5b01475
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C4 H4 N2'
_chemical_formula_sum            'C4 H4 N2'
_chemical_formula_weight         80.09
_chemical_melting_point          325
_chemical_name_common            pyrazine
_chemical_name_systematic
; 
pyrazine phase III
;
_space_group_IT_number           58
_space_group_name_Hall           '-P 2n 2'
_space_group_name_H-M_alt        'P m n n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2'
_symmetry_space_group_name_H-M   'P m n n'
_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            2
_cell_length_a                   9.307(9)
_cell_length_b                   5.706(6)
_cell_length_c                   3.623(3)
_cell_measurement_reflns_used    740
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      4.19
_cell_volume                     192.4(3)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2004)'
_computing_data_reduction
'CrysAlisRED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A.  2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL--97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS--97 (Sheldrick, 1997)'
_diffrn_ambient_environment      'diamond-anvil cell'
_diffrn_ambient_pressure         1080000
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.421
_diffrn_measured_fraction_theta_max 0.421
_diffrn_measurement_device_type  'KM-4 CCD'
_diffrn_measurement_method       'φ- and ω-scans'
_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  0.0597
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            740
_diffrn_reflns_theta_full        27.97
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         4.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Correction for absorption of the diamond-anvil cell and the sample 
 were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam
 Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr.
 219, 461-467).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cylinder
_exptl_crystal_F_000             84
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.076
_refine_diff_density_rms         0.022
_refine_ls_extinction_coef       1.68(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     20
_refine_ls_number_reflns         104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.193
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0317
_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)+(0.0176P)²+0.0445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0611
_reflns_number_gt                95
_reflns_number_total             104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b01475_si_002.cif
_cod_data_source_block           phaseIII_1.08GPa
_cod_database_code               4516575
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, -z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'-x, y, z'
'x-1/2, y-1/2, -z-1/2'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.1500(3) 0.0000 0.0000 0.0502(13) Uani 1 2 d S
C2 C 0.0730(3) 0.1813(5) 0.1231(6) 0.0462(10) Uani 1 1 d .
H2 H 0.126(2) 0.309(5) 0.227(6) 0.052(7) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0386(19) 0.052(3) 0.0605(19) 0.0107(13) 0.000 0.000
C2 0.0483(14) 0.039(3) 0.0516(15) 0.0039(11) -0.0057(9) -0.0067(12)
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C2 115.1(3) 2 .
N1 C2 C2 122.45(16) . 6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.335(3) 2
N1 C2 1.335(3) .
C2 C2 1.359(5) 6
loop_
_refln_index_h
_refln_index_k
_refln_index_l
_refln_F_squared_calc
_refln_F_squared_meas
_refln_F_squared_sigma
_refln_observed_status
1 1 0 722.37 744.21 1.59 o
3 1 0 183.51 177.90 1.03 o
5 1 0 16.75 15.45 0.52 o
2 2 0 212.37 220.56 1.56 o
4 2 0 22.06 20.61 0.30 o
6 2 0 130.58 133.78 2.97 o
5 3 0 36.11 34.46 0.45 o
7 3 0 113.92 118.68 1.31 o
8 4 0 1.06 0.56 0.29 o
1 0 1 1051.13 1025.43 12.37 o
3 0 1 133.77 134.26 3.27 o
0 1 1 732.76 714.66 7.41 o
1 1 1 378.92 368.09 5.23 o
2 1 1 0.21 0.58 0.07 o
3 1 1 0.32 0.44 0.08 o
4 1 1 108.53 109.84 2.72 o
5 1 1 39.53 38.28 0.91 o
6 1 1 6.48 5.64 0.26 o
7 1 1 20.98 18.39 0.90 o
0 2 1 97.92 99.53 2.05 o
1 2 1 1.50 1.50 0.10 o
2 2 1 35.55 37.48 1.87 o
3 2 1 128.55 135.18 4.96 o
4 2 1 1.22 1.11 0.11 o
5 2 1 11.37 9.75 0.19 o
6 2 1 17.87 17.94 0.30 o
7 2 1 58.64 60.42 2.78 o
8 2 1 7.70 6.04 0.55 o
2 3 1 66.11 69.10 0.90 o
3 3 1 0.78 0.57 0.18 o
4 3 1 9.23 9.67 0.44 o
5 3 1 1.12 1.09 0.20 o
6 3 1 71.33 70.94 8.20 o
7 3 1 1.83 2.27 0.29 o
8 3 1 14.05 14.20 0.65 o
9 3 1 0.40 1.03 0.41 o
4 4 1 0.16 0.45 0.24 o
5 4 1 0.92 0.84 0.24 o
6 4 1 15.15 16.06 0.50 o
7 4 1 9.81 10.32 0.62 o
8 4 1 7.33 6.71 0.85 o
8 5 1 1.41 1.55 0.48 o
2 0 2 7.71 7.46 0.23 o
4 0 2 23.58 25.81 0.69 o
6 0 2 10.90 10.84 0.37 o
0 1 2 205.22 212.58 0.91 o
1 1 2 34.68 34.77 1.06 o
2 1 2 53.28 52.21 1.04 o
3 1 2 54.74 53.29 0.57 o
4 1 2 8.01 8.60 0.30 o
5 1 2 0.25 0.39 0.15 o
6 1 2 33.72 35.68 0.54 o
7 1 2 11.45 11.41 0.40 o
8 1 2 13.28 12.78 0.96 o
0 2 2 70.52 69.57 1.39 o
1 2 2 69.45 71.44 0.87 o
2 2 2 3.52 3.73 0.16 o
3 2 2 0.98 0.76 0.29 o
6 2 2 9.96 9.53 0.48 o
7 2 2 14.49 14.84 0.57 o
8 2 2 0.62 0.49 0.27 o
9 2 2 1.98 1.06 0.41 o
0 3 2 4.36 3.40 0.21 o
1 3 2 5.31 4.66 0.26 o
2 3 2 3.49 3.42 0.27 o
3 3 2 13.40 13.84 0.38 o
4 3 2 0.04 0.43 0.19 o
5 3 2 0.46 0.56 0.51 o
2 4 2 1.69 1.26 0.43 o
3 4 2 3.43 2.83 0.34 o
4 4 2 4.79 4.42 0.45 o
5 4 2 10.43 10.67 0.57 o
6 4 2 4.22 4.63 0.60 o
6 5 2 4.68 3.47 0.61 o
7 5 2 1.99 1.17 0.44 o
5 0 3 4.57 5.21 0.42 o
7 0 3 19.84 22.37 0.77 o
1 1 3 15.84 12.91 1.11 o
2 1 3 5.21 5.19 0.33 o
3 1 3 0.47 0.55 0.18 o
4 1 3 4.73 4.68 0.34 o
5 1 3 4.93 4.83 0.33 o
6 1 3 8.54 7.60 0.68 o
7 1 3 5.52 6.14 0.56 o
8 1 3 1.62 2.09 0.40 o
0 2 3 19.93 19.06 0.57 o
1 2 3 22.80 21.44 1.43 o
2 2 3 3.56 3.47 0.30 o
3 2 3 4.51 4.93 0.44 o
4 2 3 2.28 1.44 0.60 o
0 3 3 37.20 38.31 0.89 o
1 3 3 0.16 0.43 0.19 o
2 3 3 1.80 1.88 0.50 o
1 4 3 1.71 0.81 0.49 o
2 4 3 3.62 2.27 0.54 o
3 4 3 3.21 3.62 0.58 o
4 4 3 0.37 0.33 0.53 o
5 5 3 0.91 1.37 0.90 o
5 1 4 0.60 1.08 0.47 o
6 1 4 0.02 0.61 0.42 o
3 2 4 0.13 0.78 0.39 o
4 2 4 1.71 0.92 0.40 o
1 3 4 10.20 10.65 1.38 o
2 3 4 0.00 0.44 0.44 o
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 9261
