#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012388.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_2012388
loop_
_publ_author_name
'Ishida, Hiroyuki'
'Rahman, Bilkish'
'Kashino, Setsuo'
_publ_section_title
;
 Morpholinium 2-chloro-4-nitrobenzoate, 2-chloro-5-nitrobenzoate and
 4-chloro-3-nitrobenzoate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1450
_journal_page_last               1453
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C4 H10 N O 1+, C7 H3 Cl N O4 1-'
_chemical_formula_moiety         'C4 H10 N O 1+, C7 H3 Cl N O4 1-'
_chemical_formula_sum            'C11 H13 Cl N2 O5'
_chemical_formula_weight         288.69
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 93.35(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.680(6)
_cell_length_b                   10.498(3)
_cell_length_c                   13.125(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      11.2
_cell_volume                     2569.4(13)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1990)
;
_computing_data_reduction
'TEXSAN for Windows (Molecular Structure Corporation, 1997-1999)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'TEXSAN for Windows'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .025
_diffrn_reflns_av_sigmaI/netI    .092
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3215
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        1.47
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .316
_exptl_absorpt_correction_T_max  .940
_exptl_absorpt_correction_T_min  .884
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .20
_refine_diff_density_max         .26
_refine_diff_density_min         -.24
_refine_ls_extinction_coef       .0240(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          .111
_refine_ls_R_factor_gt           .046
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0219P)^2^+1.0240P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .101
_refine_ls_wR_factor_ref         .121
_reflns_number_gt                1741
_reflns_number_total             2945
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ob1046.cif
_[local]_cod_data_source_block   II
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_[local]_cod_chemical_formula_sum_orig 'C11 H13 Cl N2 O5 '
_cod_original_cell_volume        2569.5(13)
_cod_database_code               2012388
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   +y,1/2-z'
'   -x,   -y,   -z'
'   +x,   -y,1/2+z'
'1/2+x,1/2+y,   +z'
1/2-x,1/2+y,1/2-z
'1/2-x,1/2-y,   -z'
1/2+x,1/2-y,1/2+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_occupancy
_atom_site_type_symbol
Cl .58105(4) .37294(7) .32979(6) .0559(3) Uani d 1 Cl
O1 .61609(11) .00193(18) .36764(15) .0556(5) Uani d 1 O
O2 .58973(9) .14191(18) .48707(14) .0506(5) Uani d 1 O
O3 .92286(11) .2335(3) .30218(17) .0784(8) Uani d 1 O
O4 .89280(11) .0791(2) .3986(2) .0720(7) Uani d 1 O
O5 .31960(10) .29981(19) .43692(15) .0550(5) Uani d 1 O
N1 .87919(12) .1750(3) .34898(18) .0527(6) Uani d 1 N
N2 .44683(12) .1719(2) .50853(18) .0432(6) Uani d 1 N
C1 .68165(12) .1917(2) .37796(17) .0335(5) Uani d 1 C
C2 .66822(13) .3131(2) .33920(18) .0377(6) Uani d 1 C
C3 .72200(16) .3875(3) .3022(2) .0472(7) Uani d 1 C
C4 .79118(16) .3433(3) .3050(2) .0477(7) Uani d 1 C
C5 .80519(13) .2243(2) .34609(18) .0392(6) Uani d 1 C
C6 .75198(13) .1480(2) .38116(18) .0371(6) Uani d 1 C
C7 .62345(12) .1057(2) .41338(18) .0373(6) Uani d 1 C
C8 .41171(17) .1445(3) .4057(2) .0527(7) Uani d 1 C
C9 .33271(16) .1724(3) .4082(2) .0523(7) Uani d 1 C
C10 .35140(16) .3231(3) .5362(2) .0524(7) Uani d 1 C
C11 .43096(15) .3038(3) .5412(2) .0475(7) Uani d 1 C
H1 .7123(15) .460(3) .275(2) .057(9) Uiso d 1 H
H2 .8270(15) .390(2) .283(2) .048(8) Uiso d 1 H
H3 .7624(12) .062(3) .4072(18) .040(7) Uiso d 1 H
H4 .4906(16) .161(3) .503(2) .049(8) Uiso d 1 H
H5 .4300(17) .108(3) .558(3) .080(10) Uiso d 1 H
H6 .4323(18) .197(3) .361(3) .073(10) Uiso d 1 H
H7 .4214(15) .055(3) .387(2) .064(9) Uiso d 1 H
H8 .3075(16) .159(3) .336(2) .062(9) Uiso d 1 H
H9 .3098(14) .117(3) .454(2) .051(8) Uiso d 1 H
H10 .3438(15) .411(3) .550(2) .060(9) Uiso d 1 H
H11 .3310(16) .268(3) .584(2) .061(9) Uiso d 1 H
H12 .4530(14) .359(2) .495(2) .045(8) Uiso d 1 H
H13 .4546(16) .311(3) .610(2) .064(9) Uiso d 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl .0463(4) .0548(4) .0658(5) .0102(3) -.0024(3) .0033(4)
O1 .0674(13) .0458(11) .0557(12) -.0179(10) .0207(10) -.0075(9)
O2 .0397(10) .0620(12) .0520(11) -.0028(9) .0180(9) -.0051(9)
O3 .0406(11) .132(2) .0645(13) -.0101(13) .0187(10) .0137(14)
O4 .0443(12) .0661(15) .1056(19) .0073(11) .0033(12) .0037(14)
O5 .0477(11) .0564(12) .0596(12) .0025(10) -.0091(9) .0078(10)
N1 .0351(12) .0757(18) .0477(14) -.0077(12) .0049(11) -.0124(13)
N2 .0307(12) .0499(14) .0497(13) -.0009(10) .0084(10) .0079(11)
C1 .0343(12) .0373(13) .0293(11) -.0034(10) .0042(10) -.0035(10)
C2 .0350(12) .0415(14) .0365(13) .0023(11) .0006(10) -.0030(11)
C3 .0600(18) .0366(15) .0451(15) -.0056(14) .0029(13) .0048(13)
C4 .0477(16) .0530(17) .0433(15) -.0184(14) .0092(13) -.0019(13)
C5 .0341(13) .0498(15) .0338(13) -.0044(12) .0026(10) -.0076(12)
C6 .0368(13) .0413(15) .0335(12) -.0042(11) .0043(10) -.0028(11)
C7 .0331(12) .0429(14) .0360(13) -.0009(11) .0032(10) .0008(11)
C8 .0596(19) .054(2) .0457(16) -.0022(15) .0125(14) .0003(14)
C9 .0526(17) .0575(19) .0457(16) -.0119(15) -.0055(14) .0068(14)
C10 .0476(17) .0522(18) .0571(19) .0045(14) .0013(15) -.0034(16)
C11 .0407(15) .0492(17) .0522(17) -.0043(13) -.0017(13) .0008(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -3 1
0 -2 3
-2 -2 -3
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O3 N1 O4 124.2(3) ?
O3 N1 C5 117.7(3) ?
O4 N1 C5 118.0(2) ?
C11 N2 H4 111.3(19) ?
C8 N2 H4 107(2) ?
C11 N2 H5 111.1(19) ?
C8 N2 H5 108.7(19) ?
H4 N2 H5 108(3) ?
C2 C1 C6 117.6(2) ?
C2 C1 C7 123.0(2) ?
C6 C1 C7 119.4(2) ?
C3 C2 C1 121.8(2) ?
C3 C2 Cl 117.8(2) ?
C1 C2 Cl 120.29(19) ?
C4 C3 C2 120.2(3) ?
C4 C3 H1 119(2) ?
C2 C3 H1 121(2) ?
C3 C4 C5 118.3(3) ?
C3 C4 H2 122.0(17) ?
C5 C4 H2 119.7(17) ?
C6 C5 C4 122.2(2) ?
C6 C5 N1 118.8(2) ?
C4 C5 N1 118.9(2) ?
C5 C6 C1 119.8(2) ?
C5 C6 H3 121.4(14) ?
C1 C6 H3 118.8(14) ?
O2 C7 O1 126.5(2) ?
O2 C7 C1 117.6(2) ?
O1 C7 C1 115.9(2) ?
N2 C8 H6 107(2) ?
C9 C8 H6 110(2) ?
N2 C8 H7 109.2(17) ?
C9 C8 H7 112.5(17) ?
H6 C8 H7 109(3) ?
O5 C9 C8 112.0(2) no
O5 C9 H8 107.0(16) ?
C8 C9 H8 110.3(17) ?
O5 C9 H9 108.6(16) ?
C8 C9 H9 111.6(16) ?
H8 C9 H9 107(2) ?
O5 C10 C11 112.2(3) no
O5 C10 H10 106.2(17) ?
C11 C10 H10 106.3(17) ?
O5 C10 H11 109.8(17) ?
C11 C10 H11 108.9(18) ?
H10 C10 H11 113(3) ?
N2 C8 C9 108.8(2) no
N2 C11 C10 109.2(2) no
N2 C11 H12 106.3(15) ?
C10 C11 H12 110.8(16) ?
N2 C11 H13 104.4(17) ?
C10 C11 H13 114.7(18) ?
H12 C11 H13 111(2) ?
C8 N2 C11 110.8(2) no
C9 O5 C10 109.7(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C2 1.743(3) yes
O1 C7 1.247(3) yes
O2 C7 1.244(3) yes
O3 N1 1.216(3) yes
O4 N1 1.218(3) yes
C1 C2 1.389(3) no
C1 C6 1.390(3) no
C1 C7 1.508(3) no
C2 C3 1.383(4) no
C3 C4 1.372(4) no
C3 H1 .86(3) ?
C4 C5 1.379(4) no
C4 H2 .89(3) ?
C5 C6 1.376(3) no
C6 H3 .98(3) ?
O5 C9 1.415(4) no
O5 C10 1.421(3) no
N1 C5 1.474(3) no
N2 C11 1.484(4) no
N2 C8 1.494(4) no
N2 H4 .83(3) ?
N2 H5 .99(4) ?
C8 C9 1.507(4) no
C8 H6 .91(3) ?
C8 H7 .99(3) ?
C9 H8 1.04(3) ?
C9 H9 .96(3) ?
C10 C11 1.497(4) no
C10 H10 .95(3) ?
C10 H11 .95(3) ?
C11 H12 .95(3) ?
C11 H13 .99(3) ?
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 N2 2.753(3) 3_656 no
O2 N2 2.719(3) . no
O2 N1 2.918(3) 7_656 no
O2 O3 3.081(3) 7_656 no
O2 C5 3.181(3) 7_656 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
N2 H4 O2 . .83(3) 1.89(3) 2.719(3) 178(2) yes
N2 H5 O1 3_656 1.00(4) 1.77(3) 2.753(3) 169(3) yes
C4 H2 O1 6_655 .89(3) 2.58(3) 3.371(4) 148(2) yes
C11 H13 O3 7_656 .98(3) 2.55(3) 3.344(4) 138(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
_geom_torsion_publ_flag
C6 C1 C2 C3 1.8(4) ?
C7 C1 C2 C3 -176.5(2) ?
C6 C1 C2 Cl 178.40(18) ?
C7 C1 C2 Cl .1(3) ?
C1 C2 C3 C4 -1.4(4) ?
Cl C2 C3 C4 -178.1(2) ?
C2 C3 C4 C5 -.5(4) ?
C3 C4 C5 C6 1.9(4) ?
C3 C4 C5 N1 179.6(2) ?
O3 N1 C5 C6 167.6(2) yes
O4 N1 C5 C6 -13.0(4) yes
O3 N1 C5 C4 -10.1(4) ?
O4 N1 C5 C4 169.3(2) ?
C4 C5 C6 C1 -1.5(4) ?
N1 C5 C6 C1 -179.1(2) ?
C2 C1 C6 C5 -.3(3) ?
C7 C1 C6 C5 178.0(2) ?
C2 C1 C7 O2 -63.1(3) yes
C6 C1 C7 O2 118.7(3) ?
C2 C1 C7 O1 119.8(3) yes
C6 C1 C7 O1 -58.5(3) ?
C11 N2 C8 C9 -54.4(3) ?
C10 O5 C9 C8 -60.5(3) ?
N2 C8 C9 O5 57.7(3) ?
C9 O5 C10 C11 60.4(3) ?
C8 N2 C11 C10 54.5(3) ?
O5 C10 C11 N2 -57.6(3) ?