#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/26/2232662.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_2232662
loop_
_publ_author_name
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
_publ_section_title
;
 4-Chloro-2-nitrobenzoic acid--pyrazine (2/1)
;
_journal_coeditor_code           FJ2468
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3222
_journal_paper_doi               10.1107/S1600536811046113
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '2C7 H4 Cl N O4, C4 H4 N2'
_chemical_formula_moiety         '2(C7 H4 Cl N O4), C4 H4 N2'
_chemical_formula_sum            'C18 H12 Cl2 N4 O8'
_chemical_formula_weight         483.22
_chemical_name_systematic
;
4-Chloro-2-nitrobenzoic acid--pyrazine (2/1)
;
_space_group_IT_number           14
_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
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.858(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   4.87662(13)
_cell_length_b                   13.5385(3)
_cell_length_c                   14.7981(6)
_cell_measurement_reflns_used    16875
_cell_measurement_temperature    110.0(10)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.0
_cell_volume                     976.89(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110.0(10)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19734
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492.00
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.393
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.2334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2535
_reflns_number_total             2833
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2468.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2232662
_cod_database_fobs_code          2232662
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 1.52398(5) 0.692432(19) 0.490381(17) 0.02257(8) Uani d . 1 1
O O1 0.69354(15) 0.47150(5) 0.18863(5) 0.02033(15) Uani d . 1 1
O O2 0.54429(14) 0.62747(5) 0.17436(5) 0.01875(15) Uani d . 1 1
O O3 0.99168(16) 0.77178(6) 0.14572(5) 0.02218(16) Uani d . 1 1
O O4 0.72288(16) 0.82806(6) 0.25018(5) 0.02337(17) Uani d . 1 1
N N1 0.89159(16) 0.76980(6) 0.22167(5) 0.01549(16) Uani d . 1 1
N N2 0.18864(16) 0.54745(6) 0.05617(5) 0.01577(16) Uani d . 1 1
C C1 0.90441(18) 0.59589(7) 0.27806(6) 0.01446(17) Uani d . 1 1
C C2 0.99232(19) 0.69339(6) 0.28474(6) 0.01377(17) Uani d . 1 1
C C3 1.18351(19) 0.72540(7) 0.34825(6) 0.01557(18) Uani d . 1 1
H H3 1.2416 0.7923 0.3504 0.019 Uiso calc R 1 1
C C4 1.28706(19) 0.65599(7) 0.40871(7) 0.01698(18) Uani d . 1 1
C C5 1.2038(2) 0.55818(7) 0.40559(7) 0.01984(19) Uani d . 1 1
H H5 1.2757 0.5117 0.4478 0.024 Uiso calc R 1 1
C C6 1.0143(2) 0.52883(7) 0.34015(7) 0.01845(19) Uani d . 1 1
H H6 0.9584 0.4617 0.3376 0.022 Uiso calc R 1 1
C C7 0.70336(18) 0.55797(7) 0.20900(6) 0.01475(17) Uani d . 1 1
C C8 0.18281(19) 0.44916(7) 0.04969(6) 0.01661(18) Uani d . 1 1
H H8 0.3099 0.4109 0.0841 0.020 Uiso calc R 1 1
C C9 0.00621(19) 0.59808(7) 0.00657(6) 0.01588(18) Uani d . 1 1
H H9 0.0056 0.6682 0.0098 0.019 Uiso calc R 1 1
H H2 0.429(4) 0.6024(14) 0.1346(14) 0.050(5) Uiso d . 1 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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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
C7 O2 H2 . . 110.7(12)
O4 N1 O3 . . 125.45(9)
O4 N1 C2 . . 117.09(8)
O3 N1 C2 . . 117.41(8)
C9 N2 C8 . . 117.35(8)
C2 C1 C6 . . 117.15(8)
C2 C1 C7 . . 124.91(8)
C6 C1 C7 . . 117.93(8)
C3 C2 C1 . . 123.33(8)
C3 C2 N1 . . 115.18(8)
C1 C2 N1 . . 121.47(8)
C2 C3 C4 . . 117.45(9)
C2 C3 H3 . . 121.3
C4 C3 H3 . . 121.3
C5 C4 C3 . . 121.48(9)
C5 C4 Cl1 . . 119.20(7)
C3 C4 Cl1 . . 119.32(7)
C4 C5 C6 . . 119.28(9)
C4 C5 H5 . . 120.4
C6 C5 H5 . . 120.4
C5 C6 C1 . . 121.31(9)
C5 C6 H6 . . 119.3
C1 C6 H6 . . 119.3
O1 C7 O2 . . 124.96(9)
O1 C7 C1 . . 121.69(9)
O2 C7 C1 . . 113.35(8)
N2 C8 C9 . 3_565 121.03(8)
N2 C8 H8 . . 119.5
C9 C8 H8 3_565 . 119.5
N2 C9 C8 . 3_565 121.62(9)
N2 C9 H9 . . 119.2
C8 C9 H9 3_565 . 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C4 . 1.7313(10)
O1 C7 . 1.2095(11)
O2 C7 . 1.3183(11)
O2 H2 . 0.88(2)
O3 N1 . 1.2323(11)
O4 N1 . 1.2195(11)
N1 C2 . 1.4727(12)
N2 C9 . 1.3343(12)
N2 C8 . 1.3344(13)
C1 C2 . 1.3909(12)
C1 C6 . 1.3932(13)
C1 C7 . 1.4964(12)
C2 C3 . 1.3836(12)
C3 C4 . 1.3875(13)
C3 H3 . 0.9500
C4 C5 . 1.3855(14)
C5 C6 . 1.3866(13)
C5 H5 . 0.9500
C6 H6 . 0.9500
C8 C9 3_565 1.3888(13)
C8 H8 . 0.9500
C9 C8 3_565 1.3888(13)
C9 H9 . 0.9500
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
O2 H2 N2 . 0.88(2) 1.80(2) 2.6739(10) 178(2)
C3 H3 O1 2_755 0.95 2.51 3.4305(12) 162
C6 H6 O3 2_745 0.95 2.59 3.4865(13) 157
C8 H8 O1 . 0.95 2.55 3.2201(12) 128
C9 H9 O3 1_455 0.95 2.45 3.1273(12) 128
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_4
_geom_torsion
C6 C1 C2 C3 . 1.03(14)
C7 C1 C2 C3 . -178.46(9)
C6 C1 C2 N1 . 179.18(9)
C7 C1 C2 N1 . -0.31(14)
O4 N1 C2 C3 . -77.08(11)
O3 N1 C2 C3 . 100.39(10)
O4 N1 C2 C1 . 104.62(10)
O3 N1 C2 C1 . -77.91(11)
C1 C2 C3 C4 . -1.09(14)
N1 C2 C3 C4 . -179.35(8)
C2 C3 C4 C5 . 0.29(15)
C2 C3 C4 Cl1 . -179.28(7)
C3 C4 C5 C6 . 0.51(15)
Cl1 C4 C5 C6 . -179.92(8)
C4 C5 C6 C1 . -0.57(15)
C2 C1 C6 C5 . -0.16(15)
C7 C1 C6 C5 . 179.36(9)
C2 C1 C7 O1 . 157.90(10)
C6 C1 C7 O1 . -21.58(14)
C2 C1 C7 O2 . -22.11(13)
C6 C1 C7 O2 . 158.41(9)
C9 N2 C8 C9 3_565 -0.01(15)
C8 N2 C9 C8 3_565 0.01(15)
