#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:07:04 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180412 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/81/7208189.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_7208189
loop_
_publ_author_name
'Arhangelskis, Mihails'
'Lloyd, Gareth O.'
'Jones, William'
_publ_section_title
;
 Mechanochemical synthesis of pyrazine:dicarboxylic acid cocrystals and a
 study of dissociation by quantitative phase analysis
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              5203
_journal_paper_doi               10.1039/c2ce25121c
_journal_volume                  14
_journal_year                    2012
_chemical_formula_iupac          'C8 H6 O4, C4 H4 N2'
_chemical_formula_moiety         'C8 H6 O4, C4 H4 N2'
_chemical_formula_structural     'C8 H6 O4, C4 H4 N2'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_chemical_name_common            'pyrazine:phtalic acid cocrystal'
_chemical_name_systematic
;
pyrazine:phthalic acid cocrystal
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 122.2085(29)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.93440(24)
_cell_length_b                   13.59704(73)
_cell_length_c                   14.51054(72)
_cell_measurement_temperature    295
_cell_volume                     1157.62(10)
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_data_collection       'X'Pert Data Collector (Panalytical )'
_computing_structure_refinement  'Topas Academic (Coelho 2007)'
_computing_structure_solution    'DASH (David et al 2008)'
_diffrn_ambient_temperature      295
_diffrn_detector                 X'Celerator
_diffrn_measurement_device_type  'Panalytical X'pert Powder'
_diffrn_radiation_monochromator  none
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_exptl_crystal_density_diffrn    1.4128(1)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_pd_block_diffractogram_id       pyrphtalprofile
_pd_char_colour                  white
_pd_instr_location               ' ?'
_pd_meas_2theta_range_inc        0.008
_pd_meas_2theta_range_max        80
_pd_meas_2theta_range_min        3
_pd_meas_number_of_points        9215
_pd_meas_scan_method             cont
_pd_prep_temperature             293
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_prof_R_factor        0.092
_pd_proc_ls_prof_wR_expected     0.115
_pd_proc_ls_prof_wR_factor       0.122
_pd_spec_mounting                ' packed powder pellet'
_pd_spec_mount_mode              reflection
_pd_spec_shape                   flat_sheet
_pd_spec_size_axial              14
_pd_spec_size_equat              10
_pd_spec_size_thick              0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.064
_refine_ls_matrix_type           fullcycle
_refine_ls_number_constraints    0
_refine_ls_number_parameters     105
_refine_ls_number_restraints     61
_refine_ls_R_I_factor            .034
_refine_ls_structure_factor_coef Inet
_refine_ls_weighting_details     1/[Yi+σ(Yi)]
_refine_ls_weighting_scheme      sigma
_cod_data_source_file            c2ce25121c.txt
_cod_data_source_block           pyrphtal
_cod_database_code               7208189
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 '-x, -y, -z'
2 '-x, y+1/2, -z+1/2'
3 'x, -y+1/2, z+1/2'
4 'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
C12 C 0.4553(19) 0.56431(44) 0.77423(53) 1 6.65(17)
C11 C 0.5333(17) 0.59615(58) 0.87298(44) 1 6.65(17)
C10 C 0.5731(16) 0.68962(44) 0.89275(50) 1 6.65(17)
C9 C 0.5188(18) 0.75835(42) 0.80364(52) 1 6.65(17)
C8 C 0.4462(12) 0.72913(39) 0.71150(62) 1 6.65(17)
C13 C 0.4080(18) 0.63269(47) 0.68932(70) 1 6.65(17)
C14 C 0.3272(13) 0.59283(51) 0.57734(51) 1 6.65(17)
O3 O 0.3227(14) 0.64125(77) 0.49758(72) 1 6.65(17)
O4 O 0.2650(11) 0.50375(59) 0.55901(47) 1 6.65(17)
C7 C 0.39726(97) 0.81057(74) 0.62741(66) 1 6.65(17)
O1 O 0.5353(16) 0.83994(77) 0.60752(73) 1 6.65(17)
O2 O 0.17713(82) 0.83265(64) 0.56186(57) 1 6.65(17)
H12 H 0.4375(53) 0.5104(35) 0.7621(23) 1 6.65(17)
H11 H 0.5743(56) 0.5430(23) 0.9433(20) 1 6.65(17)
H10 H 0.6308(46) 0.7193(22) 0.9747(19) 1 6.65(17)
H9 H 0.5413(41) 0.8203(36) 0.8178(18) 1 6.65(17)
H14 H 0.2184(44) 0.4852(26) 0.4789(24) 1 6.65(17)
H13 H 0.1599(44) 0.8683(23) 0.5071(23) 1 6.65(17)
N1 N -0.0425(17) 0.39850(71) 0.13755(41) 1 6.65(17)
C2 C -0.0255(20) 0.49610(59) 0.16539(51) 1 6.65(17)
C3 C 0.0652(20) 0.52384(58) 0.27408(48) 1 6.65(17)
N4 N 0.1211(19) 0.45514(77) 0.34928(40) 1 6.65(17)
C5 C 0.1009(19) 0.36136(59) 0.31934(44) 1 6.65(17)
C6 C 0.0142(18) 0.33480(57) 0.21252(44) 1 6.65(17)
H2 H -0.0873(49) 0.5547(22) 0.0946(22) 1 6.65(17)
H3 H 0.0910(47) 0.5938(29) 0.3029(24) 1 6.65(17)
H5 H 0.1595(51) 0.2979(25) 0.3929(21) 1 6.65(17)
H6 H -0.0037(39) 0.2781(28) 0.1927(22) 1 6.65(17)
loop_
_audit_conform.dict_name
_audit_conform.dict_location
cif_core.dic ftp://ftp.iucr.org/pub/cif_core.dic
cif_pd.dic ftp://ftp.iucr.org/pub/cif_pd.dic
loop_
_diffrn_radiation_type
_diffrn_radiation_wavelength
CuK\a~1~ 1.54056
CuK\a~2~ 1.54439
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C6 117.7(9)
N1 C6 C5 122.1(9)
C6 C5 N4 121.7(9)
C5 N4 C3 118.2(9)
N4 C3 C2 119.6(9)
C3 C2 N1 120.5(9)
O4 C14 O3 116.6(8)
O4 C14 C13 117.3(7)
C14 C13 C12 118.4(8)
C13 C12 C11 119.9(8)
C12 C11 C10 118.8(8)
C11 C10 C9 120.1(8)
C10 C9 C8 121.3(8)
C9 C8 C13 119.7(8)
C8 C13 C12 120.1(8)
C14 C13 C8 121.4(8)
C13 C8 C7 125.3(7)
O2 C7 O1 120.5(9)
N1 C6 H6 115(2)
H5 C5 N4 117(2)
N4 C3 H3 114(2)
N1 C2 H2 117(2)
H14 O4 C14 109(2)
C13 C12 H12 120(3)
H11 C11 C10 120(2)
H10 C10 C9 119(2)
H9 C9 C8 120(2)
H13 O2 C7 109(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C5 N4 1.33(1)
C5 C6 1.379(9)
C6 N1 1.28(1)
N1 C2 1.37(1)
C2 C3 1.40(1)
C14 O4 1.27(1)
C14 O3 1.32(1)
C14 C13 1.51(1)
C13 C12 1.44(1)
C11 C12 1.31(1)
C11 C10 1.30(1)
C10 C9 1.47(1)
C9 C8 1.22(1)
C8 C13 1.343(8)
C8 C7 1.55(1)
C7 O1 1.21(2)
C7 O2 1.333(7)
C6 H6 0.81(4)
C5 H5 1.26(3)
C3 H3 1.02(4)
C2 H2 1.19(3)
O4 H14 1.06(4)
O2 H13 0.88(4)
C12 H12 0.75(5)
C11 H11 1.16(3)
C10 H10 1.11(3)
C9 H9 0.86(5)
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
O4 H14 N4 . 1.06(4) 1.68(3) 2.731(9) 175(3)
O2 H13 N1 2_555 0.88(4) 1.85(3) 2.68(1) 156(3)
