#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/91/2009160.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_2009160
loop_
_publ_author_name
' Ishida, Hiroyuki '
' Kashino, Setsuo '
_publ_section_title
;
 1:1 Complexes of chloranilic acid with pyrazine and morpholine: one-
 and two-dimensional hydrogen-bond networks
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1923
_journal_page_last               1926
_journal_paper_doi               10.1107/S0108270199009841
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C4 H10 N O 1 +, C6 H Cl2 O4 1 -'
_chemical_formula_sum            'C10 H11 Cl2 N O5'
_chemical_formula_weight         296.11
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                116.26(3)
_cell_angle_beta                 113.55(3)
_cell_angle_gamma                92.65(3)
_cell_formula_units_Z            2
_cell_length_a                   9.222(2)
_cell_length_b                   9.241(4)
_cell_length_c                   8.644(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    300
_cell_measurement_theta_max      12.0
_cell_measurement_theta_min      11.4
_cell_volume                     582.9(5)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,
 1990)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1997)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution
;
SIR92 (Altomare et al., 1993)
;
_diffrn_ambient_temperature      300
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2832
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0.51
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_type   '\y scans'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             304.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.28
_refine_ls_extinction_coef       7.3(5)\\times10^-6^
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.51
_refine_ls_goodness_of_fit_ref   1.51
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[σ²(Fo) + 0.00027|Fo|²]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.079
_refine_ls_wR_factor_ref         0.077
_reflns_number_gt                2298
_reflns_number_total             2666
_reflns_threshold_expression     I>2.00σ(I)
_cod_data_source_file            ob1016.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        582.9(6)
_cod_original_sg_symbol_H-M      'P -1       '
_cod_original_formula_sum        'C10 H11 Cl2 N O5 '
_cod_database_code               2009160
loop_
_symmetry_equiv_pos_as_xyz
'  +x,  +y,  +z'
'  -x,  -y,  -z'
loop_
_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_calc_attached_atom
_atom_site_refinement_flags
_atom_site_occupancy
Cl1 .67251(4) .70825(4) .76665(5) .03567(8) Uani d ? . 1.000
Cl2 .61634(4) .18295(4) -.00432(5) .04060(9) Uani d ? . 1.000
O1 .82570(10) .98350(10) 1.17680(10) .0324(2) Uani d ? . 1.000
O2 .91010(10) .76700(10) .62160(10) .0319(2) Uani d ? . 1.000
O3 .42100(10) .22830(10) -.34050(10) .0398(3) Uani d ? . 1.000
O4 .68490(10) .50670(10) .34360(10) .0322(2) Uani d ? . 1.000
O5 .91460(10) .26340(10) .82160(10) .0416(3) Uani d ? . 1.000
N .82060(10) .29160(10) .4836(2) .0333(3) Uani d ? . 1.000
C1 .90160(10) .98700(10) 1.0900(2) .0236(3) Uani d ? . 1.000
C2 .85110(10) .86680(10) .8888(2) .0248(3) Uani d ? . 1.000
C3 .94100(10) .87190(10) .7987(2) .0241(3) Uani d ? . 1.000
C4 .45800(10) .34950(10) -.1822(2) .0260(3) Uani d ? . 1.000
C5 .55470(10) .35820(10) .0021(2) .0264(3) Uani d ? . 1.000
C6 .59780(10) .49660(10) .1765(2) .0258(3) Uani d ? . 1.000
C7 .9542(2) .4230(2) .6780(2) .0356(4) Uani d ? . 1.000
C8 1.0330(2) .3434(2) .7981(2) .0392(4) Uani d ? . 1.000
C9 .7913(2) .1319(2) .6364(2) .0412(4) Uani d ? . 1.000
C10 .7007(2) .1974(2) .5046(2) .0384(4) Uani d ? . 1.000
H1A .806(4) .701(4) .540(5) .048 Uiso d ? S .500
H1B .715(4) .594(5) .408(6) .048 Uiso d ? S .500
H2 .760(2) .333(2) .407(3) .058(5) Uiso d ? . 1.000
H3 .858(2) .211(2) .410(2) .045(4) Uiso d ? . 1.000
H4 .904(2) .506(2) .738(2) .045(4) Uiso d ? . 1.000
H5 1.030(2) .474(2) .654(2) .045(4) Uiso d ? . 1.000
H6 1.117(2) .424(2) .922(3) .054(5) Uiso d ? . 1.000
H7 1.086(2) .257(2) .735(3) .055(5) Uiso d ? . 1.000
H8 .705(2) .080(2) .647(3) .050(5) Uiso d ? . 1.000
H9 .839(2) .051(2) .581(2) .045(4) Uiso d ? . 1.000
H10 .637(2) .261(2) .551(2) .055(5) Uiso d ? . 1.000
H11 .622(2) .100(2) .375(3) .053(5) Uiso d ? . 1.000
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.002 0.002
;International Tables for Crystallography
(Vol. C)
;
H 0.000 0.000
;International Tables for Crystallography
(Vol. C)
;
N 0.004 0.003
;International Tables for Crystallography
(Vol. C)
;
O 0.008 0.006
;International Tables for Crystallography
(Vol. C)
;
Cl 0.132 0.159
;International Tables for Crystallography
(Vol. C)
;
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -2 0
3 -1 -1
2 -2 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 C2 C1 . . 117.00(10) no
Cl1 C2 C3 . . 120.70(10) no
Cl2 C5 C4 . . 117.60(10) no
Cl2 C5 C6 . . 119.60(10) no
O1 C1 C2 . . 124.00(10) no
O1 C1 C3 . 2_777 118.00(10) no
O2 C3 C1 . 2_777 113.00(10) no
O2 C3 C2 . . 127.30(10) no
O3 C4 C5 . . 124.10(10) no
O3 C4 C6 . 2_665 118.30(10) no
O4 C6 C4 . 2_665 116.80(10) no
O4 C6 C5 . . 123.60(10) no
C1 C2 C3 . . 122.30(10) no
C1 C3 C2 2_777 2_777 119.60(10) no
C2 C1 C3 . 2_777 118.00(10) no
C3 O2 H1A . . 116(3) no
C4 C5 C6 . . 122.80(10) no
C4 C6 C5 2_665 2_665 119.60(10) no
C5 C4 C6 . 2_665 117.60(10) no
C6 O4 H1B . . 102(4) no
O5 C8 C7 . . 110.50(10) yes
O5 C8 H6 . . 109.0(10) no
O5 C8 H7 . . 109.0(10) no
O5 C9 C10 . . 111.6(2) yes
O5 C9 H8 . . 112.0(10) no
O5 C9 H9 . . 109.0(10) no
N C7 C8 . . 109.20(10) yes
N C7 H4 . . 107.0(10) no
N C7 H5 . . 107.0(10) no
N C10 C9 . . 109.30(10) yes
N C10 H10 . . 113.0(10) no
N C10 H11 . . 110.0(10) no
C7 N C10 . . 111.10(10) yes
C7 N H2 . . 114.0(10) no
C7 N H3 . . 113.0(10) no
C7 C8 H6 . . 111.0(10) no
C7 C8 H7 . . 111.0(10) no
C8 O5 C9 . . 110.10(10) yes
C8 C7 H4 . . 112.0(10) no
C8 C7 H5 . . 113.0(10) no
C9 C10 H10 . . 110.0(10) no
C9 C10 H11 . . 108.0(10) no
C10 N H2 . . 106.0(10) no
C10 N H3 . . 105.0(10) no
C10 C9 H8 . . 103.0(10) no
C10 C9 H9 . . 112.0(10) no
H2 N H3 . . 106(2) no
H4 C7 H5 . . 109(2) no
H6 C8 H7 . . 106(2) no
H8 C9 H9 . . 110(2) no
H10 C10 H11 . . 106(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C2 . . 1.730(2) yes
Cl2 C5 . . 1.726(2) yes
O1 C1 . . 1.222(2) yes
O2 C3 . . 1.295(2) yes
O2 H1A . . .90(4) no
O3 C4 . . 1.216(2) yes
O4 C6 . . 1.299(2) yes
O4 H1B . . .70(5) no
C1 C2 . . 1.439(2) yes
C1 C3 . 2_777 1.527(2) yes
C2 C3 . . 1.357(2) yes
C4 C5 . . 1.444(2) yes
C4 C6 . 2_665 1.522(2) yes
C5 C6 . . 1.355(2) yes
O5 C8 . . 1.420(2) yes
O5 C9 . . 1.424(2) yes
N C7 . . 1.489(2) yes
N C10 . . 1.492(2) yes
N H2 . . .91(2) no
N H3 . . .93(2) no
C7 C8 . . 1.507(2) yes
C7 H4 . . .97(2) no
C7 H5 . . .96(2) no
C8 H6 . . .94(2) no
C8 H7 . . 1.02(2) no
C9 C10 . . 1.504(2) yes
C9 H8 . . .97(2) no
C9 H9 . . .93(2) no
C10 H10 . . .93(2) no
C10 H11 . . .99(2) no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N 2.928(2) 1_566 no
O2 O4 2.512(2) . no
O2 N 2.964(2) 2_766 no
O2 O3 3.067(2) 2_665 no
O4 N 2.851(2) . no
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
_geom_hbond_publ_flag
O2 H1A O4 . 0.90(4) 1.72(5) 2.512(2) 145(4) yes
O2 H1A O3 2_665 0.90(4) 2.45(5) 3.067(2) 126(3) yes
O4 H1B O2 . 0.70(5) 1.92(5) 2.512(2) 142(5) yes
O4 H1B O3 2_665 0.70(5) 2.25(5) 2.686(2) 122(4) yes
N H2 O4 . 0.91(2) 1.99(2) 2.851(2) 157(2) yes
N H3 O1 1_544 0.93(2) 2.07(2) 2.928(2) 153(2) yes
N H3 O2 2_766 0.93(2) 2.27(2) 2.963(2) 131(2) yes
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_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cl1 C2 C1 O1 . . -0.5(2) no
Cl1 C2 C1 C3 . 2_777 179.90(10) no
Cl1 C2 C3 O2 . . -0.2(2) no
Cl1 C2 C3 C1 . 2_777 -179.80(10) no
Cl2 C5 C4 O3 . . -1.8(2) no
Cl2 C5 C4 C6 . 2_665 179.40(10) no
Cl2 C5 C6 O4 . . 0.1(2) no
Cl2 C5 C6 C4 . 2_665 -179.40(10) no
O1 C1 C2 C3 . . -178.10(10) no
O1 C1 C3 O2 2_777 2_777 -2.2(2) no
O1 C1 C3 C2 2_777 2_777 178.10(10) no
O2 C3 C1 C2 2_777 2_777 -177.40(10) no
O2 C3 C2 C1 . . 177.30(10) no
O3 C4 C5 C6 . . 178.2(2) no
O3 C4 C6 O4 2_665 2_665 1.2(2) no
O3 C4 C6 C5 2_665 2_665 -178.30(10) no
O4 C6 C4 C5 2_665 2_665 179.90(10) no
O4 C6 C5 C4 . . -179.90(10) no
O5 C8 C7 N . . -58.9(2) no
O5 C9 C10 N . . 56.4(2) no
C7 N C10 C9 . . -53.3(2) no
C7 C8 O5 C9 . . 62.4(2) no
C8 O5 C9 C10 . . -61.5(2) no
C8 C7 N C10 . . 54.6(2) no
