#------------------------------------------------------------------------------
#$Date: 2019-11-22 21:52:56 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/65/4516569.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_4516569
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 II
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 116.93(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.263(12)
_cell_length_b                   3.831(2)
_cell_length_c                   11.086(12)
_cell_measurement_reflns_used    1395
_cell_measurement_temperature    315.0(1)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      3.68
_cell_volume                     426.5(8)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2004)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2004)'
_computing_data_reduction        'CrysAlisRED (Oxford Diffraction, 2004)'
_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_pressure         100
_diffrn_ambient_temperature      315.0(1)
_diffrn_measured_fraction_theta_full 0.844
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_device_type  'KM-4 CCD'
_diffrn_measurement_method       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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.1587
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1395
_diffrn_reflns_theta_full        26.85
_diffrn_reflns_theta_max         26.85
_diffrn_reflns_theta_min         3.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
 Correction for absorption was made using XEMP (SHELXTL, 
 Sheldrick (1990)).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.054(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.2481
_refine_ls_R_factor_gt           0.0643
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                214
_reflns_number_total             770
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg5b01475_si_002.cif
_cod_data_source_block           phaseII_315K
_cod_original_cell_volume        426.5(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4516569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.0773(5) 0.0079(13) 0.1394(4) 0.0903(16) Uani 1 1 d .
C2 C 0.1223(5) 0.1052(13) 0.0555(7) 0.0837(18) Uani 1 1 d .
H2 H 0.2101 0.1813 0.0902 0.100 Uiso 1 1 calc R
C3 C -0.0461(7) -0.1005(13) 0.0818(7) 0.0790(18) Uani 1 1 d .
H3 H -0.0836 -0.1777 0.1364 0.095 Uiso 1 1 calc R
N11 N 0.4192(5) 0.4865(13) 0.0647(6) 0.0928(18) Uani 1 1 d .
C12 C 0.5465(8) 0.3980(14) 0.1241(6) 0.0877(19) Uani 1 1 d .
H12 H 0.5837 0.3217 0.2134 0.105 Uiso 1 1 calc R
C13 C 0.3754(6) 0.5875(15) -0.0622(7) 0.0897(19) Uani 1 1 d .
H13 H 0.2865 0.6512 -0.1107 0.108 Uiso 1 1 calc R
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_3
C2 N1 C3 114.5(5) .
N1 C2 C3 122.8(5) 3
N1 C3 C2 122.7(5) 3
C13 N11 C12 113.8(5) .
N11 C12 C13 123.3(6) 3_665
N11 C13 C12 122.9(6) 3_665
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.300(5) .
N1 C3 1.307(6) .
C2 C3 1.367(7) 3
C3 C2 1.367(7) 3
N11 C13 1.320(6) .
N11 C12 1.323(7) .
C12 C13 1.339(6) 3_665
C13 C12 1.339(6) 3_665
