#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:12:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180416 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/85/7208592.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_7208592
loop_
_publ_author_name
'Tobu, Yasuhiro'
'Ikeda, Ryuichi'
'Nihei, Taka-Aki'
'Gotoh, Kazuma'
'Ishida, Hiroyuki'
'Asaji, Tetsuo'
_publ_section_title
;
 Temperature dependence of one-dimensional hydrogen bonding in
 morpholinium hydrogen chloranilate studied by (35)Cl nuclear quadrupole
 resonance and multi-temperature X-ray diffraction.
;
_journal_issue                   35
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              12347
_journal_page_last               12354
_journal_paper_doi               10.1039/c2cp41241a
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C10 H11 Cl2 N O5'
_chemical_formula_weight         296.10
_chemical_name_common            'morpholinium hydrogen chloranilete'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                91.9817(7)
_cell_angle_beta                 116.6494(7)
_cell_angle_gamma                113.9058(7)
_cell_formula_units_Z            2
_cell_length_a                   8.62366(16)
_cell_length_b                   9.11968(17)
_cell_length_c                   9.19716(17)
_cell_measurement_reflns_used    15898
_cell_measurement_temperature    145(1)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.1
_cell_volume                     569.92(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku/MSC, 2004)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      145(1)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_sigmaI/netI    0.0082
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16941
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
(NUMABS; Higashi, 1999)
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_preparation
;
Single crystals suitable for X-ray diffraction were prepared
by slow evaporation from an acetonitrile solution of chloranilic acid
with morpholine (molar ration 1:1).
;
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0226
_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)+(0.0346P)²+0.1977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                3171
_reflns_number_total             3327
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cp41241a_2.txt
_cod_data_source_block           145K
_cod_database_code               7208592
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.76437(3) 0.16933(3) 0.70551(3) 0.01632(6) Uani 1 1 d .
Cl2 Cl -0.00158(3) 0.11683(3) 0.18059(3) 0.01894(6) Uani 1 1 d .
O1 O 1.17762(10) 0.32529(8) 0.98045(8) 0.01560(13) Uani 1 1 d .
O2 O 0.61822(9) 0.40910(8) 0.76713(8) 0.01543(13) Uani 1 1 d D
H2 H 0.546(3) 0.318(2) 0.697(3) 0.023 Uiso 0.61(3) 1 d PD
O3 O -0.34174(10) -0.07820(9) 0.22444(9) 0.01876(14) Uani 1 1 d .
O4 O 0.34730(9) 0.18450(8) 0.50794(8) 0.01538(13) Uani 1 1 d D
H4 H 0.430(4) 0.238(4) 0.609(3) 0.023 Uiso 0.39(3) 1 d PD
O5 O 0.82667(10) 0.41691(9) 0.26525(9) 0.01930(14) Uani 1 1 d .
N1 N 0.48538(12) 0.32002(10) 0.29267(10) 0.01586(15) Uani 1 1 d .
C1 C 1.09074(12) 0.40197(10) 0.98594(10) 0.01168(15) Uani 1 1 d .
C2 C 0.88716(12) 0.34931(10) 0.86496(10) 0.01213(15) Uani 1 1 d .
C3 C 0.79707(12) 0.44002(10) 0.87183(10) 0.01199(15) Uani 1 1 d .
C4 C -0.18274(12) -0.04170(10) 0.34786(11) 0.01261(15) Uani 1 1 d .
C5 C 0.00304(12) 0.05464(11) 0.35678(10) 0.01301(15) Uani 1 1 d .
C6 C 0.17907(12) 0.09823(10) 0.49729(11) 0.01263(15) Uani 1 1 d .
C7 C 0.50736(14) 0.19870(12) 0.19873(12) 0.01825(17) Uani 1 1 d .
H7A H 0.3768 0.1167 0.1037 0.022 Uiso 1 1 calc R
H7B H 0.5642 0.1378 0.2751 0.022 Uiso 1 1 calc R
C8 C 0.64020(14) 0.29164(12) 0.13244(12) 0.01934(18) Uani 1 1 d .
H8A H 0.6595 0.2123 0.0750 0.023 Uiso 1 1 calc R
H8B H 0.5768 0.3439 0.0485 0.023 Uiso 1 1 calc R
C9 C 0.80279(14) 0.53643(12) 0.34562(12) 0.01842(17) Uani 1 1 d .
H9A H 0.7374 0.5874 0.2614 0.022 Uiso 1 1 calc R
H9B H 0.9336 0.6258 0.4333 0.022 Uiso 1 1 calc R
C10 C 0.68105(14) 0.45602(12) 0.42574(12) 0.01681(16) Uani 1 1 d .
H10A H 0.7491 0.4100 0.5144 0.020 Uiso 1 1 calc R
H10B H 0.6634 0.5399 0.4787 0.020 Uiso 1 1 calc R
H1A H 0.415(2) 0.2669(19) 0.343(2) 0.029(4) Uiso 1 1 d .
H1B H 0.419(2) 0.3642(18) 0.2192(19) 0.026(4) Uiso 1 1 d .
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
_geom_angle_site_symmetry_3
C3 O2 H2 116.9(17) .
C6 O4 H4 108(3) .
C8 O5 C9 110.28(7) .
C10 N1 C7 111.29(7) .
C10 N1 H1A 108.6(10) .
C7 N1 H1A 110.4(10) .
C10 N1 H1B 109.3(10) .
C7 N1 H1B 108.8(9) .
H1A N1 H1B 108.3(13) .
O1 C1 C2 123.16(8) .
O1 C1 C3 118.55(7) 2_767
C2 C1 C3 118.29(7) 2_767
C3 C2 C1 121.61(8) .
C3 C2 Cl1 121.31(6) .
C1 C2 Cl1 117.03(6) .
O2 C3 C2 127.25(8) .
O2 C3 C1 112.69(7) 2_767
C2 C3 C1 120.05(7) 2_767
O3 C4 C5 123.71(8) .
O3 C4 C6 118.37(8) 2_556
C5 C4 C6 117.91(7) 2_556
C6 C5 C4 122.84(8) .
C6 C5 Cl2 119.33(7) .
C4 C5 Cl2 117.82(6) .
O4 C6 C5 123.84(8) .
O4 C6 C4 116.92(7) 2_556
C5 C6 C4 119.24(7) 2_556
N1 C7 C8 109.38(8) .
N1 C7 H7A 109.8 .
C8 C7 H7A 109.8 .
N1 C7 H7B 109.8 .
C8 C7 H7B 109.8 .
H7A C7 H7B 108.2 .
O5 C8 C7 111.34(8) .
O5 C8 H8A 109.4 .
C7 C8 H8A 109.4 .
O5 C8 H8B 109.4 .
C7 C8 H8B 109.4 .
H8A C8 H8B 108.0 .
O5 C9 C10 110.91(8) .
O5 C9 H9A 109.5 .
C10 C9 H9A 109.5 .
O5 C9 H9B 109.5 .
C10 C9 H9B 109.5 .
H9A C9 H9B 108.0 .
N1 C10 C9 108.90(7) .
N1 C10 H10A 109.9 .
C9 C10 H10A 109.9 .
N1 C10 H10B 109.9 .
C9 C10 H10B 109.9 .
H10A C10 H10B 108.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.7314(9) .
Cl2 C5 1.7242(9) .
O1 C1 1.2284(10) .
O2 C3 1.2969(10) .
O2 H2 0.821(17) .
O3 C4 1.2195(11) .
O4 C6 1.2944(10) .
O4 H4 0.835(19) .
O5 C8 1.4267(12) .
O5 C9 1.4281(12) .
N1 C10 1.4932(12) .
N1 C7 1.5024(12) .
N1 H1A 0.917(16) .
N1 H1B 0.897(15) .
C1 C2 1.4416(11) .
C1 C3 1.5258(12) 2_767
C2 C3 1.3613(11) .
C3 C1 1.5258(12) 2_767
C4 C5 1.4428(12) .
C4 C6 1.5227(12) 2_556
C5 C6 1.3594(11) .
C6 C4 1.5227(12) 2_556
C7 C8 1.5092(13) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.5133(13) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
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
O1 C1 C2 C3 -177.98(8) . .
C3 C1 C2 C3 2.45(13) 2_767 .
O1 C1 C2 Cl1 -0.32(12) . .
C3 C1 C2 Cl1 -179.90(6) 2_767 .
C1 C2 C3 O2 177.12(8) . .
Cl1 C2 C3 O2 -0.43(13) . .
C1 C2 C3 C1 -2.49(13) . 2_767
Cl1 C2 C3 C1 179.95(6) . 2_767
O3 C4 C5 C6 178.02(9) . .
C6 C4 C5 C6 -0.93(14) 2_556 .
O3 C4 C5 Cl2 -1.65(12) . .
C6 C4 C5 Cl2 179.40(6) 2_556 .
C4 C5 C6 O4 179.98(8) . .
Cl2 C5 C6 O4 -0.35(13) . .
C4 C5 C6 C4 0.94(14) . 2_556
Cl2 C5 C6 C4 -179.39(6) . 2_556
C10 N1 C7 C8 -53.54(10) . .
C9 O5 C8 C7 -61.29(10) . .
N1 C7 C8 O5 56.49(10) . .
C8 O5 C9 C10 62.16(10) . .
C7 N1 C10 C9 54.30(10) . .
O5 C9 C10 N1 -58.33(10) . .
