#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012389.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_2012389
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'
_cell_angle_alpha                90
_cell_angle_beta                 109.09(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.76(2)
_cell_length_b                   10.085(7)
_cell_length_c                   13.639(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    296
_cell_measurement_theta_max      12.4
_cell_measurement_theta_min      11.1
_cell_volume                     2569(3)
_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      296
_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    .077
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3198
_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_%        none
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .316
_exptl_absorpt_correction_T_max  .925
_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    1.493
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1200.0
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .25
_refine_diff_density_max         .25
_refine_diff_density_min         -.20
_refine_ls_extinction_coef       .0053(4)
_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   1.03
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          .098
_refine_ls_R_factor_gt           .047
_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^)+2.0068P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .098
_refine_ls_wR_factor_ref         .116
_reflns_number_gt                1850
_reflns_number_total             2945
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ob1046.cif
_[local]_cod_data_source_block   III
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_[local]_cod_chemical_formula_sum_orig 'C11 H13 Cl N2 O5 '
_cod_database_code               2012389
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 1.17692(3) .32746(7) .71584(6) .0542(2) Uani d 1 Cl
O1 .83337(9) .49794(19) .51908(17) .0551(6) Uani d 1 O
O2 .87669(10) .69523(19) .57879(17) .0600(6) Uani d 1 O
O3 1.13261(12) .7507(2) .66169(19) .0721(7) Uani d 1 O
O4 1.20375(10) .6031(2) .74928(19) .0742(7) Uani d 1 O
O5 .93652(10) 1.0593(2) .6065(2) .0685(7) Uani d 1 O
N1 1.14522(10) .6378(2) .69468(17) .0425(5) Uani d 1 N
N2 .80195(10) .9304(2) .53913(18) .0415(5) Uani d 1 N
C1 .95747(11) .5167(2) .60193(17) .0292(5) Uani d 1 C
C2 1.01702(12) .5977(2) .63248(18) .0308(5) Uani d 1 C
C3 1.08556(11) .5438(2) .66716(17) .0299(5) Uani d 1 C
C4 1.09512(11) .4071(2) .67291(17) .0327(5) Uani d 1 C
C5 1.03493(12) .3269(3) .64108(19) .0368(6) Uani d 1 C
C6 .96719(12) .3806(2) .60579(18) .0318(5) Uani d 1 C
C7 .88264(11) .5755(3) .56369(18) .0344(5) Uani d 1 C
C8 .83071(15) .9979(4) .4643(3) .0567(8) Uani d 1 C
C9 .91125(16) .9987(4) .5074(3) .0637(9) Uani d 1 C
C10 .91069(17) .9912(4) .6780(3) .0596(9) Uani d 1 C
C11 .83031(16) .9912(4) .6432(3) .0554(8) Uani d 1 C
H1 1.0113(13) .691(3) .6308(18) .041(7) Uiso d 1 H
H2 1.0399(13) .228(3) .6427(18) .042(7) Uiso d 1 H
H3 .9274(13) .322(2) .5834(18) .037(7) Uiso d 1 H
H4 .8170(15) .842(3) .545(2) .050(8) Uiso d 1 H
H5 .7490(18) .941(3) .516(2) .068(9) Uiso d 1 H
H6 .8137(19) .949(3) .397(3) .084(12) Uiso d 1 H
H7 .8124(16) 1.093(3) .463(2) .068(10) Uiso d 1 H
H8 .9282(16) .910(3) .516(2) .063(10) Uiso d 1 H
H9 .9276(17) 1.051(3) .464(2) .074(11) Uiso d 1 H
H10 .9286(17) .893(4) .684(2) .078(11) Uiso d 1 H
H11 .927(2) 1.037(4) .737(3) .108(15) Uiso d 1 H
H12 .8142(19) .951(3) .696(3) .086(12) Uiso d 1 H
H13 .8107(17) 1.078(3) .634(2) .072(10) 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 .0297(3) .0566(5) .0721(5) .0162(3) .0107(3) .0181(4)
O1 .0234(8) .0544(13) .0792(15) .0038(8) .0055(9) -.0024(10)
O2 .0403(10) .0404(11) .0920(16) .0157(9) .0115(10) -.0041(10)
O3 .0583(13) .0485(13) .0971(18) -.0207(11) .0083(12) .0153(12)
O4 .0281(10) .0741(16) .1012(18) -.0086(10) -.0053(11) -.0002(13)
O5 .0377(11) .0541(13) .0997(19) -.0195(10) .0034(11) .0003(13)
N1 .0317(11) .0463(13) .0469(13) -.0085(10) .0091(10) -.0020(10)
N2 .0192(9) .0354(12) .0632(15) .0000(9) .0043(9) -.0034(11)
C1 .0251(10) .0332(12) .0293(12) .0042(9) .0089(9) .0015(10)
C2 .0306(11) .0274(12) .0343(13) .0004(9) .0106(10) -.0004(10)
C3 .0234(10) .0346(13) .0309(12) -.0028(9) .0076(9) .0013(10)
C4 .0251(10) .0404(13) .0321(13) .0077(10) .0087(9) .0073(10)
C5 .0332(12) .0307(13) .0464(15) .0050(10) .0130(11) .0064(11)
C6 .0263(11) .0319(12) .0369(13) -.0015(9) .0099(10) .0022(10)
C7 .0241(11) .0401(14) .0385(14) .0060(10) .0093(10) .0030(11)
C8 .0348(14) .070(2) .060(2) .0003(14) .0078(14) .0103(17)
C9 .0360(15) .076(2) .079(3) .0007(16) .0187(16) .025(2)
C10 .0420(15) .066(2) .059(2) -.0076(15) -.0001(15) -.0185(17)
C11 .0423(15) .061(2) .062(2) .0041(14) .0162(15) -.0108(17)
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
2 0 -4
3 -1 -4
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_publ_flag
O4 N1 O3 122.5(2) ?
O4 N1 C3 120.0(2) ?
O3 N1 C3 117.4(2) ?
C11 N2 H4 107.7(16) ?
C8 N2 H4 108.1(17) ?
C11 N2 H5 106.8(18) ?
C8 N2 H5 109.1(18) ?
H4 N2 H5 114(2) ?
C2 C1 C6 118.8(2) ?
C2 C1 C7 120.7(2) ?
C6 C1 C7 120.5(2) ?
C1 C2 C3 120.7(2) ?
C1 C2 H1 119.8(15) ?
C3 C2 H1 119.5(15) ?
C4 C3 C2 120.4(2) ?
C4 C3 N1 123.0(2) ?
C2 C3 N1 116.6(2) ?
C5 C4 C3 118.3(2) ?
C5 C4 Cl 116.5(2) ?
C3 C4 Cl 125.14(18) ?
C6 C5 C4 121.1(2) ?
C6 C5 H2 118.5(15) ?
C4 C5 H2 120.4(14) ?
C5 C6 C1 120.7(2) ?
C5 C6 H3 118.3(15) ?
C1 C6 H3 121.0(15) ?
O2 C7 O1 126.5(2) ?
O2 C7 C1 117.3(2) ?
O1 C7 C1 116.2(2) ?
N2 C8 H6 109(2) ?
C9 C8 H6 111(2) ?
N2 C8 H7 103.2(18) ?
C9 C8 H7 109.0(18) ?
H6 C8 H7 116(3) ?
O5 C9 C8 111.9(3) no
O5 C9 H8 107.0(18) ?
C8 C9 H8 109.1(19) ?
O5 C9 H9 106(2) ?
C8 C9 H9 107(2) ?
H8 C9 H9 116(3) ?
O5 C10 C11 111.4(3) no
O5 C10 H10 108.7(18) ?
C11 C10 H10 108.6(18) ?
O5 C10 H11 105(3) ?
C11 C10 H11 109(3) ?
H10 C10 H11 114(3) ?
N2 C8 C9 109.1(3) no
N2 C11 C10 109.4(3) no
N2 C11 H12 115(2) ?
C10 C11 H12 110(2) ?
N2 C11 H13 104.1(19) ?
C10 C11 H13 113(2) ?
H12 C11 H13 106(3) ?
C8 N2 C11 111.1(2) no
C9 O5 C10 110.7(2) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C4 1.727(3) yes
O1 C7 1.242(3) yes
O2 C7 1.237(3) yes
O3 N1 1.220(3) yes
O4 N1 1.204(3) yes
N1 C3 1.463(3) no
C1 C2 1.380(3) no
C1 C6 1.384(3) no
C1 C7 1.518(3) no
C2 C3 1.391(3) no
C2 H1 .95(3) ?
C3 C4 1.390(3) no
C4 C5 1.386(3) no
C5 C6 1.377(3) no
C5 H2 1.00(3) ?
C6 H3 .95(2) ?
O5 C9 1.416(4) no
O5 C10 1.418(4) no
N2 C11 1.479(4) no
N2 C8 1.486(4) no
N2 H4 .93(3) ?
N2 H5 1.00(3) ?
C8 C9 1.505(4) no
C8 H6 1.00(3) ?
C8 H7 1.02(3) ?
C9 H8 .95(3) ?
C9 H9 .93(3) ?
C10 C11 1.501(4) no
C10 H10 1.05(4) ?
C10 H11 .89(4) ?
C11 H12 .96(4) ?
C11 H13 .95(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 2.629(4) 7_666 no
O2 N2 2.752(3) . no
C2 C6 3.372(4) 3_766 no
C4 C7 3.400(4) 3_766 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 . .93(3) 1.85(3) 2.752(4) 160(3) yes
N2 H5 O1 7_666 .99(4) 1.66(4) 2.629(4) 164(3) yes
C5 H2 O5 1_545 1.00(3) 2.58(3) 3.269(5) 125.9(19) yes
C8 H6 O4 8_464 1.00(4) 2.49(4) 3.335(6) 142(3) yes
C10 H10 O2 . 1.05(4) 2.48(4) 3.255(6) 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
_geom_torsion_publ_flag
C6 C1 C2 C3 -.4(4) ?
C7 C1 C2 C3 -179.8(2) ?
C1 C2 C3 C4 -.9(4) ?
C1 C2 C3 N1 178.1(2) ?
O4 N1 C3 C4 -20.3(4) yes
O3 N1 C3 C4 160.9(3) yes
O4 N1 C3 C2 160.8(2) ?
O3 N1 C3 C2 -18.1(3) ?
C2 C3 C4 C5 1.5(4) ?
N1 C3 C4 C5 -177.5(2) ?
C2 C3 C4 Cl -179.21(18) ?
N1 C3 C4 Cl 1.9(4) ?
C3 C4 C5 C6 -.8(4) ?
Cl C4 C5 C6 179.8(2) ?
C4 C5 C6 C1 -.5(4) ?
C2 C1 C6 C5 1.1(4) ?
C7 C1 C6 C5 -179.6(2) ?
C2 C1 C7 O2 -12.9(4) yes
C6 C1 C7 O2 167.7(2) ?
C2 C1 C7 O1 166.3(2) yes
C6 C1 C7 O1 -13.0(3) ?
C11 N2 C8 C9 54.2(4) ?
C10 O5 C9 C8 59.7(4) ?
N2 C8 C9 O5 -56.4(4) ?
C9 O5 C10 C11 -59.9(4) ?
C8 N2 C11 C10 -55.0(4) ?
O5 C10 C11 N2 57.5(4) ?