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#$Date: 2019-11-17 09:18:47 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229063 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/02/7230253.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_7230253
loop_
_publ_author_name
'Rok, M.'
'Bator, G.'
'Sawka-Dobrowolska, W.'
'Durlak, P.'
'Moskwa, M.'
'Medycki, W.'
'Sobczyk, L.'
'Zamponi, M.'
_publ_section_title
;
 Crystal structural analysis of methyl-substituted pyrazines with anilic
 acids: a combined diffraction, inelastic neutron scattering, 1H-NMR study
 and theoretical approach
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2016
_journal_paper_doi               10.1039/C8CE00040A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C6 H2 Br2 O4, C5 H6 N2'
_chemical_formula_sum            'C11 H8 Br2 N2 O4'
_chemical_formula_weight         392.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-01-06 deposited with the CCDC.
2018-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.35(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.001(2)
_cell_length_b                   4.845(4)
_cell_length_c                   16.024(4)
_cell_measurement_reflns_used    3553
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.3930
_cell_measurement_theta_min      3.1070
_cell_volume                     1266.5(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5110
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         3.117
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.412
_exptl_absorpt_correction_T_max  0.817
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1451
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0376
_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)+(0.0326P)²+5.4830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1341
_reflns_number_total             1451
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00040a2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7230250--7230254.cif.'
_cod_original_cell_volume        1266(3)
_cod_database_code               7230253
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.446
_shelx_estimated_absorpt_t_max   0.784
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21442(2) 0.11998(8) 0.30382(3) 0.01742(15) Uani 1 1 d . . . . .
O2 O 0.12309(18) 0.1268(6) 0.4049(2) 0.0197(6) Uani 1 1 d . . . . .
H1 H 0.1042 0.1380 0.4399 0.030 Uiso 1 1 calc R U . . .
O3 O 0.15464(17) -0.1828(5) 0.5642(2) 0.0173(6) Uani 1 1 d . . . . .
C11 C 0.2321(2) -0.0869(7) 0.4143(3) 0.0153(8) Uani 1 1 d . . . . .
C13 C 0.2003(2) -0.2179(7) 0.5382(3) 0.0135(7) Uani 1 1 d . . . . .
C12 C 0.1845(2) -0.0503(7) 0.4481(3) 0.0149(8) Uani 1 1 d . . . . .
N1 N 0.0384(2) 0.3244(7) 0.4713(3) 0.0186(7) Uani 1 1 d . . . . .
C3 C 0.0509(2) 0.3027(8) 0.5621(3) 0.0182(8) Uani 1 1 d . . . . .
H3 H 0.0869 0.1638 0.6082 0.022 Uiso 1 1 calc R U . . .
C2 C -0.0127(3) 0.5224(9) 0.4083(3) 0.0194(8) Uani 1 1 d . . . A 1
C21 C -0.0227(5) 0.5700(18) 0.3094(6) 0.0225(18) Uani 0.5 1 d . . P A 1
H21A H 0.0308 0.6095 0.3231 0.034 Uiso 0.5 1 calc R U P A 1
H21B H -0.0595 0.7270 0.2737 0.034 Uiso 0.5 1 calc R U P A 1
H21C H -0.0461 0.4046 0.2666 0.034 Uiso 0.5 1 calc R U P A 1
H2 H -0.0226 0.5444 0.3444 0.027 Uiso 0.5 1 d . U P B 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C12 O2 H1 109.5 . .
C12 C11 C13 122.2(3) . 7_546
C12 C11 Br1 121.0(3) . .
C13 C11 Br1 116.8(3) 7_546 .
O3 C13 C11 124.6(4) . 7_546
O3 C13 C12 117.7(3) . .
C11 C13 C12 117.7(3) 7_546 .
O2 C12 C11 122.1(4) . .
O2 C12 C13 117.7(3) . .
C11 C12 C13 120.1(3) . .
C3 N1 C2 117.3(3) . .
N1 C3 C2 122.1(4) . 5_566
N1 C3 H3 119.0 . .
C2 C3 H3 119.0 5_566 .
N1 C2 C3 120.6(4) . 5_566
N1 C2 C21 119.0(5) . .
C3 C2 C21 120.1(5) 5_566 .
N1 C2 H2 119.7 . .
C3 C2 H2 119.6 5_566 .
C21 C2 H2 4.4 . .
C2 C21 H21A 109.5 . .
C2 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C2 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C2 C21 H2 7.1 . .
H21A C21 H2 116.0 . .
H21B C21 H2 108.4 . .
H21C C21 H2 103.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C11 1.881(4) .
O2 C12 1.319(5) .
O2 H1 0.8400 .
O3 C13 1.215(5) .
C11 C12 1.353(5) .
C11 C13 1.453(5) 7_546
C13 C11 1.453(5) 7_546
C13 C12 1.521(5) .
N1 C3 1.331(5) .
N1 C2 1.338(5) .
C3 C2 1.395(6) 5_566
C3 H3 0.9500 .
C2 C3 1.395(6) 5_566
C2 C21 1.496(9) .
C2 H2 0.9304 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C21 H2 0.5723 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H1 N1 0.84 1.89 2.645(4) 149.4 .
C3 H3 O3 0.95 2.50 3.124(5) 123.2 .
C21 H21C O2 0.98 2.62 3.530(9) 155.4 2
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C13 C11 C12 O2 -180.0(4) 7_546 .
Br1 C11 C12 O2 1.2(5) . .
C13 C11 C12 C13 -0.6(6) 7_546 .
Br1 C11 C12 C13 -179.4(3) . .
O3 C13 C12 O2 1.3(5) . .
C11 C13 C12 O2 180.0(3) 7_546 .
O3 C13 C12 C11 -178.2(4) . .
C11 C13 C12 C11 0.5(6) 7_546 .
C2 N1 C3 C2 0.0(7) . 5_566
C3 N1 C2 C3 0.0(7) . 5_566
C3 N1 C2 C21 174.7(5) . .
